The Undertaker

Calaway began training under Buzz Sawyer in late 1986;[5][27] he disliked Sawyer, who reportedly lacked commitment and provided a limited education.[5][6] Calaway learned "on the job" thereafter.[28] Performing under a mask as Texas Red,[6] Calaway wrestled his first match on June 26, 1987, for World Class Championship Wrestling (WCCW), losing to Bruiser Brody at the Dallas Sportatorium.[7][29] He was accompanied to the ring by Percival "Percy" Pringle III, who would later serve as his manager in the WWF (as Paul Bearer).[6][30] Two myths have circulated regarding Calaway's beginnings in the industry, the first being that he made his in-ring debut in 1984,[5] and the second being that he was trained by former WCCW colleague Don Jardine (aka The Spoiler).[31][32] While never trained by Jardine, Calaway was an admirer of his work and would emulate Jardine's top rope walk.[33][34] PWInsider's Mike Johnson stated, "Undertaker using some of Jardine's style eventually morphed into this story that he was trained by Jardine."[28]

In 1988, Calaway joined the Continental Wrestling Association (which became part of the United States Wrestling Association (USWA) after Jerry Jarrett bought WCCW and merged the two organizations into one), wrestling under several gimmicks. On February 2, 1989, managed by Dutch Mantel, he was reintroduced as The Master of Pain, a character fresh out of the United States Penitentiary, Atlanta after serving five years (much in solitary confinement) for killing two men in a fight.[35] After his second match the next week, he stayed in the ring by challenging USWA Unified World Heavyweight Champion Jerry Lawler to an impromptu match. The Master of Pain easily dominated Lawler until Mantel entered the ring and called him off. Lawler agreed to a title match and on April 1, The Master of Pain won his first professional wrestling championship. He held it for just over three weeks before Lawler became the first man to pin him, winning it back. While performing as The Punisher, Calaway won the WCWA Texas Heavyweight Championship on October 5, 1989, when Eric Embry forfeited the title.[36]

In 1989, Calaway joined World Championship Wrestling (WCW) as a villain and adopted the ring name "Mean Mark" Callous, a name devised for him by Terry Funk.[37] He was portrayed as a sinister force, wearing predominantly black ring attire and was described by announcer Jim Ross as having a fondness for pet snakes and the music of Ozzy Osbourne.[38] Callous was promptly drafted into The Skyscrapers tag team to replace a legitimately injured Sid Vicious, and he made his debut on January 3, 1990, in a match later televised against Agent Steel and Randy Harris.[39] The new team gained some notoriety at Clash of the Champions X when they beat down The Road Warriors after their match (the Road Warriors were actually very impressed by this).[40] However, Callous's partner Dan Spivey left WCW days before their Chicago Street Fight against The Road Warriors at WrestleWar. Callous and a replacement masked Skyscraper were defeated in the street fight and the team broke up soon afterwards.[41] Now a singles wrestler, Callous took on the guidance of Paul E. Dangerously (Paul Heyman) and defeated Johnny Ace at Capital Combat and Brian Pillman at Clash of the Champions XI: Coastal Crush.

Calaway later began to question his future in WCW after being told by company booker, Ole Anderson, during contract renewal discussions that nobody would ever pay money to watch him perform.[5] It was in response to this that Calaway sought to achieve more noteworthy success in professional wrestling by making numerous efforts to join the World Wrestling Federation, going to many lengths to land a meeting with Vince McMahon. However, accessing and securing an interview with McMahon was described by Calaway as a despairing task.[42]

Among routes Calaway took to land a meeting with McMahon was trying to convince individuals acquainted with McMahon or already existing WWF talent to recommend him into the WWF, such as Hulk Hogan, Paul Heyman, Bruce Prichard, etc. While linking up with Hogan for a small role as "Hutch" during the making of the movie Suburban Commando, Calaway was able to get a recommendation sent to McMahon from him. Hogan's effectiveness is questioned because he was reportedly on bad terms with McMahon at this particular point.[42][43] In 2014, however, Hogan publicly took sole credit for The Undertaker meeting McMahon, and becoming employed with the WWF: Hogan shared that he had The Undertaker cast for the Suburban Commando movie role, and while taping for the movie in 1990, he decided to introduce Calaway to McMahon. According to Hogan, it was in that meeting he set up between the three of them that Vince immediately took to Calaway, and decided to call him "The Undertaker" right then and there in front of Hogan.[44] However, The Undertaker has shared a vastly contrasting account from Hogan's, rather crediting WWF Executive Bruce Prichard and Paul Heyman for landing him the meeting with Vince McMahon.[45]

Callous wrestled Lex Luger for the NWA United States Heavyweight Championship at The Great American Bash, but was pinned. According to Prichard, "feelers" had already been sent out to the WWF by Heyman: Calaway wrestled the match with a dislocated hip knowing that he was being watched by McMahon. In reviewing the match, McMahon wasn't impressed by Calaway's wrestling performance, considering him "run-of-the-mill" and thus disinterested.[45] However, Calaway shared that Prichard and Heyman were determined and maintained belief in Calaway.[45] It was Prichard who managed to encourage McMahon to arrange for a meeting with Calaway when WCW traveled to New Jersey for a house show in the Meadowlands[33] on August 24.[39]

Calaway immediately gave notice to WCW without yet having had the meeting with McMahon and only having received McMahon's invite—one that went beyond an invite to Titan Towers where most WWF job interviews were said to have taken place, but rather an invite to be flown out to McMahon's Stamford, Connecticut mansion.[45] After an extended hour and a half meeting in which Calaway described trying not to present as nervous, McMahon ended the session by telling Calaway that the WWF had nothing for him at this time, but that maybe they would at the beginning of the coming year, January 1991. This disappointed Calaway as he had given WCW his notice, thus jobless for however long until McMahon decided to send him an offer.[45] However, a few days later, McMahon randomly called up Calaway and asked "Is this The Undertaker?" to which Calaway contemplated for a moment before responding, "Yea, I'm The Undertaker," and expressing initial satisfaction that he wasn't a laughingstock character akin to "The Gobbledy Gooker" or "Mr. Shower Guy" (having regrettably told Vince he could sing well in the shower during their meeting).[45] According to Calaway, Vince had the "Old West Undertaker" idea in mind for years but had never found the right wrestler to play the part.[45]

Calaway's final match was on September 7 at a WorldWide taping in Amarillo, Texas in which he defeated Dave Johnson.[39] During his time in WCW, Calaway briefly wrestled in New Japan Pro-Wrestling (NJPW) as "Punisher" Dice Morgan.[46] After leaving WCW, he briefly returned to the USWA to participate in a tournament to determine the new USWA Unified World Heavyweight Champion; Calaway defeated Bill Dundee in the first round, but lost to Jerry Lawler in the quarterfinals.

In October 1990, Calaway signed with the World Wrestling Federation (WWF), set to portray the "brainchild" of McMahon that he had assigned to him, originally entitled Kane the Undertaker[45] ("Kane" later added on to "The Undertaker" moniker by the time of his arrival at the urgings of Bruce Prichard, who had always desired a Cain and Abel effect for his character).[47] Despite Calaway's perplexed, pessimistic feelings about McMahon's gimmick idea, he was readily accepting of the role, feeling anything better than the laughingstock gimmicks of that time, such as The Gobbledy Gooker.[42][48][45] Kane the Undertaker was characterized as a menacing derivative of the Wild West undertakers depicted in television westerns. Resulting from that, this very first edition of The Undertaker's series of Deadman incarnations[42][48] has been distinguished in external media as "The Old West Mortician".[49][50] He made his overall WWF debut on a November 19, 1990, taping of WWF Superstars quickly defeating his very first opponent, Mario Mancini, in a singles match[51] (this match was filmed three days prior to The Undertaker's televised debut at the November 22 Survivor Series, but did not air on television until December 15, 1990). Also prior to his Survivor Series appearance, Kane the Undertaker had a match on November 20 against Rick Sampson, which later aired on the December 9, 1990, edition of WWF Wrestling Challenge.[52]

Calaway's official televised debut was the Survivor Series event in which he was presented as the heel mystery partner of Ted DiBiase's "Million Dollar Team".[53] Approximately one minute into the match, The Undertaker eliminated Koko B. Ware with his finisher, the Tombstone Piledriver.[54] (In 2018, Koko B. Ware shared that directly following this match that night, he confronted The Undertaker with serious objections to what he felt was a botched Tombstone. Though Ware also shared that he always admired Mark Calaway and perceived him as a great performer).[55] During the match, The Undertaker also eliminated Dusty Rhodes before being counted out; however, his team won the match with DiBiase being the sole survivor.[54] During the match, Calaway was referred to as simply The Undertaker, omitting the portion "Kane", which was dropped shortly after the event (and seven years later at the urgings of Prichard, given to another wrestler once he took on the role of The Undertaker's younger brother).[47][54] Throughout the end of 1990, The Undertaker mostly picked up squash victories against jobbers on Superstars of Wrestling and Wrestling Challenge tapings.[54] He was a participant in the 1991 Royal Rumble match which was won by Hulk Hogan.[54]

In February 1991, Brother Love delegated his short-lived management role of The Undertaker over to Paul Bearer (real-life funeral director), Love communicating the need for someone who better aligned with The Undertaker's "deadman" themes.[56] Histrionic, wailing and ghostly in character, Bearer complemented The Undertaker and was almost always seen bearing an urn which he raised in the air to transmit supernatural healing powers to The Undertaker; this typically resulted in The Undertaker recovering from attacks and counterattacking his adversaries.[56] During his early years, The Undertaker took to a post-match ritual of placing his defeated opponents (almost always jobbers) in a body bag and carrying them backstage.[57] He continued picking up victories in squash matches leading up to his first feud in the WWF with "Superfly" Jimmy Snuka.[54]

The Undertaker made his WrestleMania debut at WrestleMania VII on March 24, 1991, quickly defeating "Superfly" Jimmy Snuka.[58] He began his first major feud shortly thereafter, which was with The Ultimate Warrior when The Undertaker attacked Warrior and locked him in an airtight casket on the set of Paul Bearer's Funeral Parlor segment.[54] Resulting from this, the Warrior enlisted the assistance of Jake "The Snake" Roberts to get him mentally psyched for The Undertaker's morbid alarmist tactics: Roberts would drill the Warrior with "know your enemy" training, setting up the Warrior in a series of creepy, terrorizing circumstances, such as by locking him in caskets and in rooms with snakes.[59][54] This culminated in a final stage of Roberts's training in which Roberts proved to be stringing Warrior along the entire time by assisting The Undertaker in an ambush.[59] The Undertaker would later suffer his first losses in the WWF to The Ultimate Warrior, including in a first ever body bag challenge, a casket match, and (at house show) standard pin-fall match.[60] The feud was, however, cut short after the Warrior's suspension and ongoing issues with Vince McMahon.[60] In the 1991 King of the Ring, Undertaker defeated Animal in a qualifying match before fighting Sid Vicious to a double disqualification in the semifinal, which saw both men eliminated from the King of the Ring tournament.[61] The Undertaker defeated Hulk Hogan to win his first WWF Championship at Survivor Series with the help of Ric Flair and thus became the youngest WWF Champion in history to that point, 26 years of age—this record was later broken by Yokozuna in April 1993 at WrestleMania IX.[62] The Undertaker's Tombstone of Hogan to win the WWF Championship at the 1991 Survivor Series created real-life, offscreen discord between the two, which Undertaker attributes his short title reign, lack of title runs during his early career and distrust of Hogan.[63] In storyline, however, WWF President Jack Tunney ordered a rematch between the two at This Tuesday in Texas six days later, where The Undertaker lost the title back to Hogan.[62] However, due to the controversial endings of the two title matches between The Undertaker and Hogan, the title was vacated from Hogan the next night by Tunney. The company was without a WWF Champion until Ric Flair earned it by winning 1992 Royal Rumble match.[64]

In February 1992, The Undertaker's ally Jake "The Snake" Roberts tried to attack "Macho Man" Randy Savage's manager/wife Miss Elizabeth with a steel chair when Undertaker stopped him, turning him (and Paul Bearer) face for the first time. Their face turn was solidified on the February 29 edition of Superstars when Roberts confronted The Undertaker on the Funeral Parlor set over the matter (aired on Saturday Night's Main Event XXX). After demanding to know whose side The Undertaker was on and getting the reply, "Not yours", Roberts attacked both Bearer and The Undertaker, only for The Undertaker to stand his ground and run Roberts off. The Undertaker defeated Roberts at WrestleMania VIII.[58] He then feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993, such as Kamala and Giant González. Also during this time, The Undertaker headlined the first ever episode of Monday Night Raw on January 11, 1993, with a victory over Damien Demento.[65][66] According to Calaway, working with González "...was survival every night trying to figure out what he could do" and "took years off my career".[67] He faced González at WrestleMania IX, which is notable as The Undertaker's only disqualification win at WrestleMania after the use of chloroform.[68] The Undertaker's next rivalry initiated at the 1993 Survivor Series with Yokozuna when a clash between the two lost control, causing them to be counted out in an elimination tag match.[69] In the weeks following, The Undertaker and Bearer spooked Yokozuna with multiple segments from their wintery and remote rural area workshop. There, Bearer presented The Undertaker hard at work carpentering Yokozuna what would eventually become a "double wide, double deep casket" custom-built for Yokozuna's immensely overweight size.[70] The feud culminated in a WWF Championship casket match at the Royal Rumble in January 1994. During the match, Yokozuna sealed The Undertaker in the casket with the assistance of a multitude of heel wrestlers (some of them Whippleman-managed) hired by Yokozuna's vindictive managers Jim Cornette and Mr. Fuji, which was in retaliation for Bearer's casket match stipulation that he snuck into their Royal Rumble match contract. After being trapped inside the casket by the pack, green vapor emitted from the casket and the arena lights went out. Undertaker then appeared from inside the casket on the video screen, representing the spirit of his dead corpse, warning that he would produce a future "rebirth" of himself, explaining to his antagonists that he cannot and will not Rest in Peace.[71] The Undertaker did not appear in the WWF for seven months after his loss to Yokozuna. In reality, he was given time off to allow a back injury to heal.[72]

Paul Bearer betrayed The Undertaker by hitting him with the urn that he is seen carrying

Following the death angle at the Royal Rumble during The Undertaker's absence, the WWF promoted reported sightings of him through video clips of random people claiming to have seen him. After WrestleMania X, Ted DiBiase introduced an Undertaker back to the WWF. This Undertaker, however, played by Brian Lee (one of Calaway's real-life best friends)[73] was an impostor Undertaker (dubbed "The Underfaker" by fans)[74] rejuvenated by Dibiase's money rather than Bearer's urn. His actions led to the return of the real Undertaker at SummerSlam, defeating the impostor and appearing as a reincarnation of his Deadman gimmick, one of a more shadowy, mysterious and secret presence.[75] Represented now by cool colors, The Undertaker replaced details of his wrestling gear that were previously colored gray with purple, and effected scenes with blue/purple semidarkness.[75] Many details that would become associated with The Undertaker for the remainder of his career were produced during this rebirth incarnation, such as the addition of sleeve tattoos and Godlike supernatural elements (thunder, lightning and windy weather-like effects used to indicate The Undertaker's presence and wrath).[76][77]

Seeking retribution, The Undertaker revisited his feud with Yokozuna and eventually faced him in a casket rematch at the 1994 Survivor Series. Chuck Norris (portraying his Walker, Texas Ranger persona) was involved in the match as special guest enforcer, preventing interference from wrestlers that Yokozuna, Jim Cornette and Mr. Fuji had again enlisted for help.[78] Unable to rely on much as far as interference this time around (only Irwin R. Schyster able to get in a brief ambush) due to Norris averting the attempts of several heel wrestlers, Yokozuna was defeated by The Undertaker and sealed in the casket.[78] Throughout most of 1995, Undertaker feuded with members of Ted DiBiase's Million Dollar Corporation. The chain of wrestlers DiBiase enlisted to do away with The Undertaker started with Irwin R. Schyster at the Royal Rumble for which The Undertaker was victorious, but assaulted by another member of the Million Dollar Team, King Kong Bundy. In the process of being assaulted, Bearer was deprived of his urn by the Corporation.[79] At WrestleMania XI, The Undertaker made short work of Bundy in a singles match. This edition of WrestleMania is noteworthy in that it produced the first mention of The Undertaker's historic WrestleMania-winning Streak, acknowledged on commentary by Vince McMahon as Undertaker made his entrance: "The Undertaker, on his way to the ring—a man who's never lost at WrestleMania."[80] During The Undertaker's WrestleMania encounter, DiBiase issued him with yet another antagonist in "The Supreme Fighting Machine" Kama, who had stolen the briefly recaptured urn from Bearer during the match. Kama followed this up with a series of malicious acts, including destroying the stolen urn and recycling it into bling.[81][79] While sporting the flashy bling around his neck, he repeatedly cost The Undertaker matches and attacked diehard Undertaker fans, dubbed "Creatures of the Night".[81][71] In August, Undertaker settled the score with Kama, defeating him in a casket match at SummerSlam.[71] Several weeks later, Undertaker suffered a serious orbital bone injury when King Mabel unintentionally struck him in the eye with his fist during a house show, forcing The Undertaker into a period of absence for surgery. Due to the incident happening at a house show, Vince McMahon had it presented to the audience as though it had occurred from Mabel and Yokozuna's exchange of leg drops and splashes on The Undertaker on the Monday Night Raw that had aired 2 days prior.[82] The Undertaker returned a couple months later at Survivor Series, in which he single-handedly eliminated an entire team of wrestlers led by King Mabel, The Undertaker leading his own team to victory.[83] It was at that Survivor Series return in which he began wearing a Phantom of the Opera-like, gray upper-face mask to safeguard his orbital injury while it healed.[71] The following month in December, The Undertaker defeated Mabel in a casket match at In Your House, finally retrieving back the urn (though still in its bling form) in the process, which had been traded around between several of The Undertaker's antagonists over the entire course of that year.[82]

In the main event of the Royal Rumble in January 1996, The Undertaker was unmasked of his Phantom of the Opera-like facial covering in a WWF Championship match against Bret Hart. The Undertaker was eventually able to hit the Tombstone Piledriver on Hart, but Diesel interfered, costing The Undertaker the championship.[84] A rematch for the title on the February 5 episode of Raw saw similar interference.[85] At that month's In Your House: Rage in the Cage, while Diesel was facing Hart in a steel cage match for the WWF Championship, The Undertaker delivered a surprise attack, emerging from a hole he had ripped through the ring canvas and dragging Diesel with him down under amid a cloud of smoke, allowing Hart the victory.[84] After several weeks of more retaliatory one-upmanship between Diesel and The Undertaker, their feud culminated in a singles match at WrestleMania XII, where Undertaker was victorious.[58]

The Undertaker's next feud commenced the next night on Raw when Mankind, a twisted and tortured soul, made his debut and randomly interfered in Undertaker's match against Justin "Hawk" Bradshaw. For the next few months, Mankind viciously ambushed The Undertaker and cost him multiple matches.[84] Among them, Mankind cost The Undertaker the WWF Intercontinental Championship by interfering in his casket match against Goldust at In Your House 8: Beware of Dog. In interfering in this match, Mankind proved to have mystifying horror tactic capabilities that matched The Undertaker's, mysteriously appearing from inside the casket and sealing The Undertaker inside. The Undertaker, however, had vanished amid a cloud of smoke once the casket lid was opened.[86] As a result of the interference and repeated ambushes from Mankind on The Undertaker throughout the ensuing weeks, The Undertaker and Mankind competed in their very first on-screen bout at the 1996 King of the Ring, a heated encounter in which The Undertaker presented as uncharacteristically intense.[86] During the match, Bearer inadvertently hit The Undertaker with the urn, allowing Mankind to incapacitate The Undertaker with his finisher, the Mandible Claw, and score the win.[86] With Mankind insatiably continuing to cost The Undertaker matches even following their King of the Ring encounter, The Undertaker began firing back with rage and the feud spiraled out of control: the two routinely interrupted other matches already in progress, battling each other at random intervals outside of having arranged matches—their chaos also spilling into audiences, arena backstage communal areas, and arena boiler rooms, all of this unprecedented at the time.[86] As a result, the first ever Boiler Room Brawl (Mankind's specialty match) was booked between the two at SummerSlam.[86] After more than 20 minutes of brawling with Mankind in the Cleveland Gund Arena's boiler room, the arena corridors, the SummerSlam entrance area and aisleway to the ring, The Undertaker reached for Paul Bearer's urn in an attempt to win the match, but Bearer struck him with it, betraying The Undertaker. This followed with Bearer allowing Mankind to take hold of the urn, thus winning this match.[84] After Bearer's betrayal, The Undertaker grew more aggressive, resolving his feud against Goldust (Mankind's comrade in tormenting The Undertaker) at In Your House 10: Mind Games. The Undertaker then took his rivalry with Mankind to new lengths in a specialty match of his own, and at that time unprecedented Buried Alive match to take place in the main event of In Your House 11: Buried Alive. The Undertaker won the match after chokeslamming Mankind into the open grave and subsequently shoveling enough dirt on him so that he was covered. However, after interference from the debuting Executioner, as well as the help of several other heel wrestlers apparently enlisted by Bearer, Mankind escaped the grave and together the mob all shoveled dirt onto The Undertaker to the point that the grave was completely filled, resulting in The Undertaker fully buried alive. Not without a parting message for the pack, however, The Undertaker's purple glove fit hand emerged from his burying place amid a bolt of lightning that had erupted over the gravesite. The scene sent all of his antagonists fleeing.[84]

After being buried alive and a following month-long hiatus, The Undertaker returned at the Survivor Series again pitting him against Mankind, but with a unique stipulation: Hanging 6.1 m (20 ft) above the ring would be Paul Bearer, enclosed in a steel cage. And if The Undertaker were to win the match, he would be rewarded the opportunity to assault Bearer however he pleased. Even though The Undertaker won this match, interference from The Executioner enabled Bearer to escape Undertaker's clutches.[87] It was also at this event that The Undertaker had developed a comparatively more humanized and more informal yet still superhuman "Deadman" incarnation. In this then new form, he took on a Goth appearance and persona, with a brash, rebelling, Championship-driven mean streak (perhaps to better fit in with the then-budding, more adult-oriented Attitude Era).[88] This delivering, dubbed "The Lord of Darkness", was the 3rd incarnation of his Deadman persona.[88] Following Survivor Series, The Undertaker briefly turned his attention to The Executioner, who had been interfering in his matches since his arrival. At In Your House 12: It's Time, The Undertaker defeated The Executioner in an Armageddon Rules match even with Mankind heavily involved throughout the entire encounter.[87] The Undertaker then moved on to feud with Vader, whom he faced in January 1997 at the Royal Rumble in a singles match, which The Undertaker lost after Bearer interfered on behalf of his new protégé.[87] The two then clashed in the Royal Rumble match itself as they made it to the final moments of the match, but both were eliminated by Stone Cold Steve Austin, who had crept back into the match after his elimination was unseen. He faced both Vader and Austin in a four-corners elimination match for the vacant WWF Championship at In Your House 13: Final Four, but Bret Hart won.[89] However, the following month, The Undertaker managed to win the WWF Championship for the second time by defeating Sycho Sid at WrestleMania 13.[90] Reviving his first Deadman incarnation for that night only, The Undertaker appeared as the "Old West Mortician", donning the trademarked gray wrestling gear accessories (boot spats, tie, gloves), along with a pitch-black entrance with only a white spotlight shined over him, contrasted from the purple/blue semidarkness associated with the rest of his Deadman incarnations.[88]

Following his WWF Championship win at WrestleMania 13, Paul Bearer attempted to rejoin The Undertaker as his manager. After The Undertaker refused and attacked Bearer, Bearer had Mankind set a fireball to the Undertaker's face, leading up to a match at In Your House 14: Revenge of the 'Taker, for which The Undertaker was victorious.[91] Evening the score at "Revenge of the 'Taker", The Undertaker set a fireball to Bearer's face directly following the match.[91] Following the event, Bearer bandaged up from fire burns, likened The Undertaker's assault to a past incident he described as The Undertaker's "deepest, darkest secret". Through giving The Undertaker the ultimatum of revealing his deepest, darkest secret to the world, Bearer was able to reunite with him as manager and protégé. After only a few months of abrasive behaviors from Bearer, however, The Undertaker lost his patience and rejected Bearer as his manager. In retaliation, Bearer disclosed that The Undertaker had intentionally killed his family by burning down his parents' family funeral home for which they raised him and his younger brother.[92] (Note that the younger brother, Kane, was not revealed to be The Undertaker's half-brother until the following year, April 1998, when Bearer disclosed to the world that he is Kane's father, The Undertaker's mother having had an affair with him. Bearer later verified this with DNA test results).[93] At this point in his career, The Undertaker denied the charges of committing the arson murder that killed his family; however, Bearer claimed to have proof in the form of The Undertaker's alive and well younger brother, Kane, who had survived though scarred and burned. Bearer raised Kane after the fire, having him institutionalized from the date of the fire into adulthood. Ever since the fire, Kane had been awaiting to exact vengeance on his older half-brother. In defense, Undertaker responded that Kane, a "pyromaniac", had been the one to set the fire and, as a result, could not have possibly even survived.[92] (Note that it would not be until a year and a half later from this point, in latter 1998, in which The Undertaker would shamelessly confess to intentional acts of arson to the funeral home that killed his parents and scarred his brother).[92]

The Undertaker as "Lord of Darkness" Deadman in September 1997

In spite of Bearer projecting himself as a constant source of mental distress to The Undertaker during his Championship title reign, The Undertaker managed to secure successful title defenses against Stone Cold Steve Austin (A Cold Day In Hell: In Your House),[94] Faarooq (King of the Ring)[95] and Vader (Canadian Stampede: In Your House, revisiting and settling their Royal Rumble feud from earlier on in the year),[96] respectively. Concurrent to the "deep, dark secret" storyline directed by Bearer, Undertaker began a then new rivalry at SummerSlam when special guest referee Shawn Michaels accidentally hit him with a steel chair shot intended for his archnemesis Bret Hart, in effect, costing The Undertaker the WWF Championship.[90] The accidental chair shot led to Michaels feeling betrayed by the now booing WWF fans, and quickly becoming heel. Thus, a severely violent storyline with The Undertaker followed, one revolving around repeated intentional chair shots by Michaels on The Undertaker, Michaels taunting The Undertaker throughout.[97] After the duo's very first match, which was a chaotic and uncontrolled encounter that resulted in a double count-out draw at Ground Zero: In Your House, Undertaker challenged Michaels to the first ever Hell in a Cell match to take place at Badd Blood: In Your House. Despite the inclusion of the cell for more order and to prevent Michaels from receiving help from his D-Generation X stable, the encounter ended up even more uncontrolled and savage than their first and is considered among one of The Undertaker's best matches of his career.[98] Seemingly about to emerge the victor after striking Michaels with a chair shot of his own, The Undertaker was interrupted by his storyline half-brother Kane, finally making his debut. Under the control of Paul Bearer, Kane stormed the arena, ripped off the cell door, and laid out a nonplussed Undertaker with his own trademarked finisher, The Tombstone Piledriver, allowing Michaels to pin him for the victory.[90] As the storyline progressed through Bearer having Kane mow down much of the WWF roster, Kane repeatedly challenged The Undertaker, going to lengths of tormenting and humiliating him. However, The Undertaker consistently refused to fight his half-brother, claiming he had made a vow to his parents never to do harm to his own "flesh and blood".[99] The Undertaker's final encounter with Michaels during this chapter of his career was in a casket match for the WWF Championship at the Royal Rumble. The week before on Raw, Kane had duplicitously presented as allying with his brother against Michaels's D-Generation X stable; however, at the Royal Rumble, Kane trapped The Undertaker in the coffin, padlocked the lid shut, and set the casket ablaze, allowing Michaels another victory.[100] After a two-month hiatus in which Kane wreaked havoc over the WWF, The Undertaker returned on the March 2, 1998, edition of Raw in a most notable resurrection—his druids interrupting Kane and Bearer by presenting them with a coffin on the entrance stage amid a large number of bell tolls. The coffin was struck and dismantled by a lightning bolt, revealing a lied out Undertaker who sat up in a fury state and challenged Kane to do battle with him.[101] At WrestleMania XIV in their first match, The Undertaker defeated Kane.[100] Kane challenged Undertaker to a rematch—Kane's specialty and first ever Inferno match—that occurred one month later at Unforgiven: In Your House. The Undertaker won the encounter by setting Kane's right arm on fire.[100]

The Undertaker and Mankind's wildly violent, outlandish feud from over a year previous to this point was revitalized over the next month, ultimately taken to a new graphic height and decisively resolved when they faced each other in a Hell in a Cell match at King of the Ring. The match became one of the most famous matches in professional wrestling history. During the match, The Undertaker threw Mankind off the roof of the 4.9 m (16 ft) cell onto a broadcast table below, in what was a preplanned move. He later performed a chokeslam on Mankind through the roof of the cell into the ring, which was not preplanned and legitimately knocked Mankind unconscious. In jumping from the top of the cell to the ring canvas, The Undertaker suffered a broken ankle. Escalating as things progressed, blood flowed from both wrestlers as they attacked each other with steel steps, chairs, the cell wall, etc. Topping that off, Mankind introduced multitudes of thumbtacks scattered across the ring canvas but was back body dropped on them, and subsequently chokeslammed onto them before The Undertaker won the match with his Tombstone Piledriver.[100] At Fully Loaded: In Your House, The Undertaker and Stone Cold Steve Austin defeated Kane and Mankind to win the WWF Tag Team Championship.[100] The Undertaker and Austin's reign as tag team champions lasted only two weeks, as Kane and Mankind regained the titles from them in a fatal four-way tag-team match on the August 10 edition of Raw.[102][103] The Undertaker then became the number one contender for the WWF Championship, held by Austin at that point, for a match at SummerSlam. Shortly before SummerSlam and after much speculation, The Undertaker finally disclosed that he and his half-brother were working together. Despite this revelation, The Undertaker told Kane before his SummerSlam bout that he did not want him interfering, even sending Kane away during the match itself when he appeared. Even though The Undertaker lost the match at SummerSlam, he handed Austin his championship belt back after the match with a show of respect and sportsmanship.[100]

In September as the storyline matured however, The Undertaker subtly began showing some heel characteristics, becoming a tweener. This began when he and Kane revealed the fact that they were in cahoots to rid Austin of his title for villainous company owner Mr. McMahon—Austin and McMahon immersed in a bitter rivalry during this era. At Breakdown: In Your House, The Undertaker and Kane were booked in a triple threat match with Austin for the WWF Championship, in which McMahon stated that the brothers were not allowed to pin each other. The Undertaker and Kane pinned Austin simultaneously after a double chokeslam, ending the match in a no contest, so the title was vacated by McMahon.[100] This event led to a match at Judgment Day: In Your House between The Undertaker and Kane for the title, with Austin as the special guest referee. Near the end of the match, Paul Bearer seemed about to assist Kane by handing him a steel chair to hit The Undertaker with, but as Kane had his back turned, both Bearer and The Undertaker hit Kane with chair shots. The Undertaker went for the pin, but Austin refused to count the fall, attacked The Undertaker and counted out both of them.[100] Finally, The Undertaker turned heel the next night on Raw for the first time since 1992, reconciling with Bearer and claiming that he and Bearer would unleash their "Ministry of Darkness" on the WWF. As part of the then new storyline angle, The Undertaker admitted that he had indeed intentionally set the fire that killed his parents and scarred Kane, for which he had previously blamed on Kane.[104]

After Survivor Series, The Undertaker returned his attention to his previous feud with Austin for costing him the title at Judgment Day, hitting Austin in the head with a shovel during a title match with The Rock on the November 16 edition of Raw, returning the favor for what happened a month earlier. With this twist in the storyline, Mr. McMahon scheduled a Buried Alive match between The Undertaker and Austin at Rock Bottom: In Your House. In the weeks leading up to Rock Bottom, The Undertaker attempted to embalm Austin alive, tried to have Kane committed to a mental asylum, and had his druids chain Austin to an immense structure of his Undertaker crucifix-like logo (which took the appearance of a capital T combined X) before having that structure lifted up on high into the air.[105][106] However, The Undertaker lost the Buried Alive match to Austin at Rock Bottom after Kane interfered.[107]

After the buildup to his second heel run in the latter part of 1998, The Undertaker introduced an updated version of his Deadman identity by January 1999—a dark priest-like character who in the initial period of this persona reigned over a stable known as The Ministry of Darkness. In this form, he took on a wicked, demonic presence, much more so than ever before. He often proclaimed to be invoking and taking orders from a "Higher Power". Moreover, he often appeared in a hooded black robe and sat on a throne with a towering backrest specially designed into his crucifix-like logo. With the help of his minions, he often performed sacrifices on select WWF wrestlers, using various incantations and magic words with intent to extract out the dark side of the wrestlers in question to recruit them into his Ministry. The completed Ministry of Darkness consisted of The Brood (Christian, Edge and Gangrel), The Acolytes (Bradshaw and Faarooq), Mideon and Viscera. Calaway himself did not wrestle for a period, having undergone a hip replacement. As part of the angle, Undertaker had his Ministry members fight his battles, carry out his evil wishes and do all his dirty deeds. In this manner, he expressed his desires to take over the World Wrestling Federation, displacing its owner, Mr. McMahon. These ambitions culminated into a rivalry between The Ministry and The Corporation, ultimately resulting in a match between Undertaker and Corporation enforcer, Big Boss Man. The two faced off in a Hell in a Cell match at WrestleMania XV, which Undertaker won.[108] At Backlash: In Your House, Undertaker defeated Corporation member Ken Shamrock after interference from Ministry member Bradshaw.[109]

Thereafter, The Undertaker kidnapped Stephanie McMahon, forcing Mr. McMahon to enter into a reluctant alliance with his longtime nemesis Stone Cold Steve Austin. The Undertaker attempted to marry Stephanie before sacrificing her in an eldritch ceremony conducted by Paul Bearer, but Austin was able to rescue her.[110] At the Over the Edge pay-per-view, The Undertaker defeated Austin for his third WWF Championship with help from Shane McMahon, the special guest referee.[111] The Ministry eventually merged with Shane McMahon's Corporation alliance to form The Corporate Ministry. The Undertaker later revealed that Mr. McMahon had been his "Higher Power" all along as a scheme against Austin.[112] After The Undertaker lost the WWF Championship back to Austin on the Raw following King of the Ring and lost to him in a First Blood match at Fully Loaded, his relationship with the McMahons dissolved and The Corporate Ministry disbanded.[113]

The Undertaker then began a storyline where he teamed with Big Show in a tag team known as "The Unholy Alliance", which held the WWF Tag Team Championship twice. After their victory at SummerSlam, The Undertaker suffered a groin tear and was seen limping in several matches. He avoided competing in wrestling matches in the following weeks, instead overbearingly ordering Big Show to fight his battles and do all his dirty deeds. Developing a comedy horror smart mouth during this time, elements of The Undertaker's trash-talking biker identity (that he would eventually introduce in 2000) began peeping out during this phase of his career. According to an interview with Kevin Nash, this was a move to allow Calaway to enter World Championship Wrestling with a non-trademarked persona; had he entered WCW, it would have been as Mark Calaway. According to Nash, although negotiations were described as close, Calaway ultimately re-signed with the WWF. Conversely, while on Steve Austin's Broken Skull Sessions podcast on November 22, 2020, Calaway revealed that there was no way he was ever going to rejoin WCW, that the gimmick's biker transition was just a matter of him mixing things up because he didn't feel the character's Deadman side properly fit with the then ongoing Attitude Era.[114][115]

To compensate for his lack of physical activity, Undertaker became increasingly overbearing and vocal, often mouthing off with a weirdness and making sinisterly smart-aleck remarks in promos and on commentary. On the September 23, 1999, edition of SmackDown!, Mr. McMahon threatened that he would remove Undertaker from the Unforgiven main event if he refused to participate in a casket match against Triple H. Undertaker retorted that he did not care and maybe he would not be participating in anything WWF any longer, from there walking out on the WWF.[116] In reality, Calaway went on a hiatus from the WWF in order to treat his groin injury. He made his return to action on December 14, teaming with Viscera in a losing effort against Kane and The Godfather at a house show in Coamo, Puerto Rico.[117] The Undertaker was advertised on the Armageddon promotional poster to return, but meanwhile also tore his pectoral muscle, taking him out of action for almost eight months.[118]

The Undertaker at WrestleMania XIX

In May 2000, Calaway expanded on The Undertaker gimmick, returning under a human alter ego of the gimmick—a smack-talking, redneck biker, dubbed "The American Badass", known for motorcycle-riding, tobacco chewing/spitting, and donning a sporty appearance and manner.[119] In stark contrast to his horror-themed and fully fictional Deadman persona, Calaway's Badass persona was only semifictional with traits and features adopted from who he is out of character—hence, why he desired to transform The Undertaker.[120][121] While explained off screen years later for the above reasons, Calaway's sudden appearance as American Badass Undertaker after hiatus in which he left off as Deadman Undertaker was never explained within WWE storylines or the WWE's fictional universe. Rather, the expectation was for fans to just go with it.[122]

When The Undertaker returned near the end of the iron man match for the WWF Championship between Triple H and The Rock at Judgment Day, he took out all the members of the McMahon-Helmsley Faction, which created for a face turn after having left things off as a heel before his hiatus.[123] He also targeted their leader, then WWF Champion Triple H. At the King of the Ring pay-per-view, The Undertaker teamed with The Rock and Kane to defeat the team of Triple H, Shane McMahon and Vince McMahon.[124] Afterward, he was booked to team with Kane to contend for the WWF Tag Team Championship. They defeated Edge and Christian, earning the right to face them the following week for the championship, which Edge and Christian retained. During an August 14 Raw bout against Chris Benoit, Kane became involved and betrayed The Undertaker by hitting him with two chokeslams, the second one causing the ring apron to cave in underneath The Undertaker.[123] This incident led to another match between the two at SummerSlam, which ended in a no contest as Kane fled from the ring area after The Undertaker removed Kane's mask.[124]

The Undertaker then challenged Kurt Angle for the WWF Championship at Survivor Series.[125] Angle, however, defeated The Undertaker after he switched places with his real-life brother, Eric Angle. The Undertaker demanded and was awarded a spot in the six-man Hell in a Cell match for the WWF Championship at Armageddon. The Undertaker promised to make someone famous and did so when he performed a chokeslam on Rikishi from the roof of the cell into hay-filled cargo bed of a truck.[125]

In 2001, The Undertaker reunited with Kane as The Brothers of Destruction, issuing a challenge for the WWF Tag Team Championship once again. They received a title shot at No Way Out, facing Edge and Christian and then champions The Dudley Boyz in a tables match but were unsuccessful.[125] The Undertaker then went on to defeat Triple H at WrestleMania X-Seven.[58] He and Kane continued a storyline that focused on Triple H, who formed a "surprise alliance" with then WWF Champion Stone Cold Steve Austin. The Brothers of Destruction were granted an opportunity to face Triple H and Austin for their titles (Triple H was the WWF Intercontinental Champion). After The Undertaker and Kane won the WWF Tag Team Championship from Edge and Christian on the April 19 edition of SmackDown!,[126] Triple H pinned Kane after attacking him with a sledgehammer at Backlash, where The Brothers of Destruction lost their championships.[127] With Kane injured, The Undertaker feuded briefly with Austin for his WWF Championship, but he failed to win the title at Judgment Day.[127]

As part of "The Invasion" storyline, The Undertaker's next nemesis was Diamond Dallas Page, who was obsessively stalking his [The Undertaker] wife, Sara.[127] At SummerSlam, WCW Tag Team Champions The Undertaker and Kane defeated Page and his partner Kanyon in a steel cage match to win the WWF Tag Team Championship.[127] At Survivor Series, The Undertaker teamed with Kane, The Rock, Chris Jericho and Big Show to take on The Alliance's Stone Cold Steve Austin, Booker T, Rob Van Dam, Shane McMahon and Kurt Angle (this was the last time The Undertaker and Kane teamed until 2006). Angle pinned The Undertaker due to interference by Austin. Despite this, Team WWF won the match.[127]

After The Alliance was defeated, The Undertaker turned heel by inducting commentator Jim Ross into the Mr. McMahon: Kiss My Ass Club, which involved The Undertaker pressing the lips of Ross against McMahon's exposed buttocks.[128] In transitioning his "American Badass" biker identity into a heel, The Undertaker eventually cut his long hair short and went by the nickname "Big Evil". At Vengeance, The Undertaker defeated Rob Van Dam to win the WWF Hardcore Championship.[129]

The Undertaker in his "Big Evil" persona

The Undertaker's next storyline began at the Royal Rumble in January 2002, when Maven eliminated him from the Royal Rumble match by hitting him with a dropkick from behind. Subsequently, The Undertaker eliminated Maven in return and brutally assaulted him backstage.[129] Thereafter, on an edition of SmackDown!, The Rock inflamed The Undertaker's anger by mentioning his elimination at the Royal Rumble. He responded by costing The Rock the number one contendership for the undisputed WWF championship.[130] The storyline continued when The Rock cost The Undertaker his match with Maven for the Hardcore Championship.[131] The two faced off at No Way Out, where The Undertaker lost due to interference from Ric Flair.[129] This interference began a storyline with Flair, who declined a challenge to wrestle Undertaker at WrestleMania X8.[132] As a result, Undertaker assaulted his son David Flair.[133] Flair eventually accepted the match after The Undertaker threatened to inflict the same punishment on Flair's daughter.[133] A no-disqualification stipulation was added to the match and The Undertaker defeated Flair at WrestleMania.[58]

The Undertaker performing a Tombstone Piledriver on Ric Flair at WrestleMania X8

After the storyline with Flair, The Undertaker was drafted to the Raw brand after the WWF split its roster into two brands and defeated Stone Cold Steve Austin at Backlash to become the number one contender for the undisputed WWF championship. Later that night, he helped Hollywood Hulk Hogan win the title against then champion Triple H.[129] The Undertaker then defeated Hogan for the renamed WWE undisputed championship at Judgment Day. The next night on Raw, The Undertaker lost to Rob Van Dam for the WWE undisputed championship; however, Raw owner Ric Flair restarted the match (Van Dam pinned The Undertaker when his foot was on the rope, thus invalidating the pin attempt) and The Undertaker retained the championship.[134] On the July 1 edition of Raw, The Undertaker turned face once again after defeating Jeff Hardy in a ladder match to retain the WWE undisputed championship and raising Hardy's hand as a show of respect. The Undertaker, however, lost the title at Vengeance to The Rock in a triple threat match that also involved Kurt Angle.[134] On the August 29 edition of SmackDown!, Undertaker was moved to the SmackDown! brand (where he remained until the first brand extension ended in 2011), alongside former Raw talent Brock Lesnar, Chris Benoit and Eddie Guerrero. Undertaker defeated Chris Benoit and Kurt Angle in a triple threat match to become the number-one contender for the renamed WWE Championship and challenged Brock Lesnar for the title at Unforgiven that ended in a double disqualification.[134] Their feud carried over to No Mercy in a Hell in a Cell match, which The Undertaker performed with a legitimately broken hand and ultimately lost to Lesnar.[134]

The Undertaker took a break after Big Show threw him off the stage on the October 24 edition of SmackDown!, sparking a feud.[135] The Undertaker returned at the Royal Rumble in January 2003.[136] He immediately continued his feud with Big Show and defeated him by submission at No Way Out with a triangle choke. A-Train entered the storyline by attempting to attack The Undertaker after the match, but Nathan Jones came to his aid.[136] The storyline resumed as The Undertaker began to train Jones to wrestle and the two were scheduled to fight Big Show and A-Train in a tag team match at WrestleMania XIX.[58] However, Jones was removed before the match, making it a handicap match, which The Undertaker won with the help of Jones.[136]

Over the remainder of the year, The Undertaker entered a brief feud with John Cena (defeating him at Vengeance) and was booked to have two WWE Championship opportunities. The first, on the September 4 SmackDown!, against Kurt Angle, ended in a no contest, due to interference from Brock Lesnar.[137] The second, at No Mercy, was a Biker Chain match between The Undertaker and Lesnar, which Lesnar won with the help of Vince McMahon.[138] This match resulted in a feud with McMahon, culminating at Survivor Series where The Undertaker lost a Buried Alive match against McMahon when Kane interfered.[138] The Undertaker disappeared for some time following this match, with Kane claiming that he was "dead and buried forever".[139]

The Undertaker, awakening the arena lights as he enters the ring

In the storyline leading up to WrestleMania XX, Kane was tormented by horror-themed mind games, paranormal activities, and spooking vignettes proclaiming The Undertaker's Deadman return. The first was during the Royal Rumble when The Undertaker's bells tolled, distracting Kane and allowing Booker T to eliminate him.[138] Accompanied by Paul Bearer at WrestleMania XX, The Undertaker resurrected his Deadman identity, defeating Kane in a singles match.[140] Introduced was a more dramatic, theatrical and supernatural Deadman than in years past, his presence, mannerisms, and entrances significantly elaborated on as well, such as with more intensity, special effects and rising and falling flames.[141] At the same time, The Undertaker maintained elements of his American Badass identity, thus a composite character more humanized than all of his previous Deadman incarnations[142] (Undertaker would present in this particular hybrid Deadman form until No Mercy 2005 when Randy Orton sealed him in a casket and set it on fire).[141] At Judgment Day, The Undertaker defeated Booker T. One week later, Paul Heyman ordered The Dudley Boyz to kidnap Bearer.[143][144] Thus, Heyman "took control" of Undertaker.[144] At The Great American Bash, Undertaker fought a handicap match against The Dudley Boyz, with the stipulation that if he did not lay down and purposely lose, Heyman would bury Paul Bearer in cement. The Undertaker won and stopped Heyman from burying Bearer, but after claiming Bearer was merely a liability he had no use for, buried him himself.[140]

The Undertaker began a feud with then WWE Champion John "Bradshaw" Layfield (JBL) by challenging him to a title match at SummerSlam, which The Undertaker lost by disqualification.[140] At No Mercy, The Undertaker and JBL competed in the first-ever Last Ride match, although The Undertaker lost after Heidenreich interfered.[140] After defeating Heidenreich in a match at Survivor Series,[145] The Undertaker turned his focus to the WWE Championship once again. Along with Eddie Guerrero and Booker T, he challenged JBL to a championship rematch at Armageddon in a fatal four-way match, in which The Undertaker was unsuccessful, again due to Heidenreich's interference.[145] The feud culminated in a casket match between The Undertaker and Heidenreich at the Royal Rumble, where Undertaker sealed Heidenreich in a casket for the victory.[145]

Soon after, Randy Orton challenged The Undertaker to a match at WrestleMania 21, uppishly proclaiming that he would end his WrestleMania winning Streak.[146] Even with help from his father, Orton lost as The Undertaker improved his WrestleMania record to 13–0.[145] After a two-month hiatus, Undertaker returned on the June 16 edition of SmackDown!, but lost to JBL due to interference from Randy Orton, revealed as a new draft switch to SmackDown!.[147] Despite his interference, the Randy Orton/Undertaker feud was put on the back burner until late summer of that year, resulting from Orton on the injured list.[148]

In the meantime and in one of the most controversial moments in WWE history on an edition of SmackDown! taped on July 4, 2005 (aired on July 7), SmackDown! General Manager Theodore "Teddy" Long scheduled Muhammad Hassan in a match against The Undertaker at The Great American Bash, and placed Daivari in a match that night against Undertaker: Undertaker quickly defeated Daivari. After the match, however, Hassan began to "pray" on the ramp, summoning five masked men, dressed in black shirts, ski-masks and camouflage pants. Armed with clubs and a piano wire, the masked men assaulted and choked out The Undertaker before Hassan then placed The Undertaker in a camel clutch. Afterward, the masked men lifted Daivari above their heads and carried him away. Three days later, the London bombings took place. The footage aired unedited on UPN in the United States and on The Score in Canada with an advisory warning shown several times during the broadcast. It was removed from the Australian and European (including in the United Kingdom) broadcasts.[149]

The angle elicited national attention in the New York Post, TV Guide, Variety and other major media outlets. In response to the criticism, UPN decided that it would monitor the storyline closely and that it did not want the Hassan character on its network that week.[150] Hassan later delivered a promo to the live crowd for the July 14, 2005, edition of SmackDown!, but when UPN announced that the segment would be edited, WWE decided to host the video of the segment on its official website. In the segment, Hassan reiterated that he was an Arab American and that the American people automatically and unfairly assumed that he was a terrorist. Despite being in character, he referred to the real-world media coverage of the storyline, singling out the New York Post's Don Kaplan by name and denouncing his description of the events on SmackDown!, such as Kaplan's comment of the masked men being "Arabs in ski masks". On the July 14, 2005, edition of SmackDown!, Hassan's absence was explained by a statement delivered by his attorney, Thomas Whitney, Esquire, that Hassan refused to appear on the show until The Great American Bash due to the way he was treated by the American media and WWE fans.

It was revealed in late July 2005 that UPN had pressured WWE to keep Hassan off their network, effectively removing him from SmackDown!.[151] Undertaker defeated Hassan at The Great American Bash to become the number one contender to the World Heavyweight Championship. After the match, The Undertaker delivered a Last Ride through an open stage ramp onto a concrete floor to Hassan. It was reported that Hassan sustained serious injuries and had to be rushed to a nearby medical facility, writing Hassan off television.[152] Several days later, WWE.com hosted a video of a kayfabe announcement from Theodore Long, where he reiterated the stipulation that Hassan would no longer appear on SmackDown!. It was revealed years later that Hassan was about to receive a major push by winning the World Heavyweight Championship from Batista at SummerSlam and thus breaking Randy Orton's record for being the youngest World Heavyweight Champion in WWE history.[153]

On the following edition of SmackDown!, The Undertaker lost to JBL in a number-one contender's match, once again due to interference from Orton, reviving their feud that was put on hiatus.[154] At SummerSlam, Orton defeated The Undertaker in a WrestleMania rematch. The storyline intensified as the two tried to get into the head of one another with dark mind game tactics and use of caskets, leading to a handicap casket match at No Mercy, in which The Undertaker lost to Randy and his father "Cowboy" Bob Orton.[155] After the match, the Ortons poured gasoline on the casket and set it on fire (a throwback moment to one of The Undertaker's most infamous attacks received and done by Kane doing the same to him at the 1998 Royal Rumble). When the charred casket was opened, however, The Undertaker was absent, presented as having vanished.[155]

The Undertaker resurrected at the Survivor Series when the druids delivered a casket that was struck by lightning and went up in flames. The Undertaker then burst from the flaming casket in rage, battering and brutalizing an entire ring full of wrestlers as a message to Orton. Here, he reappeared still in hybrid form but with lessened Badass characteristics, eliminating several elements of his biker identity so that his Deadman side projected, most notably, replacing loose-fitting cargo pants with his Deadman spandex, and less use of the Last Ride finisher.[156] The Undertaker returned on SmackDown! in early December to haunt Orton and set up a Hell in a Cell match at Armageddon.[147] After The Undertaker won their brutal Hell in a Cell encounter, in effect, settling his 9 month long feud with Orton,[156] Calaway took a brief hiatus from professional wrestling.

The Undertaker retaining his undefeated Streak at WrestleMania 22

In January 2006 at the Royal Rumble, The Undertaker returned on a horse-drawn cart during Kurt Angle's celebration of his World Heavyweight Championship defense against Mark Henry. In this appearance, The Undertaker signaled for a title shot by using his supernatural powers to collapse the wrestling ring that Angle stood in as a means to spook him. As part of their storyline angle, The Undertaker lost his match with Angle at No Way Out after a 30-minute bout—described as underrated and among Undertaker's top matches, in which he versatilely took to a more ground-based submission style to combat Angle's trademarked freestyle wrestling.[157][158] The Undertaker cornered Angle after the match and told him he was not finished with him.[157] In a rematch with Angle (similarly described as underrated and among The Undertaker's top matches that utilized the wrestling styles of their previous encounter on the March 3 edition of SmackDown!) Henry attacked The Undertaker from behind, costing him the title.[157] This led to The Undertaker challenging Henry to a casket match at WrestleMania 22 and Henry vowing to end The Undertaker's WrestleMania winning Streak. The match resulted in The Undertaker sealing Henry in the casket, winning the match and extending his streak to 14–0 at WrestleMania.[159] During a rematch on the next edition of SmackDown!, The Great Khali made his debut and assaulted The Undertaker to transition into a new storyline.[160]

The Undertaker was not heard from until the May 5 edition of SmackDown! when Theodore Long delivered a challenge from The Undertaker to Khali for a match at Judgment Day. The Undertaker lost to Khali at Judgment Day,[161][162] and he did not appear again until the July 7 edition of SmackDown! when he accepted Khali's challenge to a Punjabi Prison match at The Great American Bash. However, Khali was removed from the match due to not being medically cleared. He was thus replaced by then ECW World Champion Big Show, over whom The Undertaker gained the victory.[163] In storyline, Theodore Long replaced Khali with Big Show as punishment for an attack on The Undertaker shortly before the match.[161] Khali was then challenged by The Undertaker to a Last Man Standing Match for SummerSlam after interfering in The Undertaker's match with then World Heavyweight Champion King Booker. Khali refused a challenge against The Undertaker for SummerSlam, however, Long announced the Last Man Standing Match ahead of time, for the August 18 edition of SmackDown! instead. The Undertaker won the match by striking Khali with steel stairs and finishing him with a chokeslam. It was Khali's first defeat and effectively ended his feud with The Undertaker.[164][165]

The Undertaker's next match was with then United States Champion Mr. Kennedy at No Mercy, but was disqualified in the match after he hit Kennedy with the championship belt.[166] On the November 3 edition of SmackDown!, The Undertaker reunited with Kane to reform The Brothers of Destruction for the first time in five years, defeating reluctant opposition in the form of Mr. Kennedy and Montel Vontavious Porter (MVP), with whom Kane was feuding with at the time.[167] As part of the storyline, Kennedy defeated The Undertaker in a First Blood match at Survivor Series after interference from MVP,[166] but finally defeated Kennedy in a Last Ride match at Armageddon.[166] The two continued to feud into 2007 as Kennedy cost The Undertaker two World Heavyweight Championship opportunities for a championship match at the Royal Rumble.[168] However, The Undertaker eventually qualified for the 2007 Royal Rumble match, by winning a battle royal on the January 26 edition of SmackDown!.[169]

The Undertaker making his entrance in 2008

The Undertaker won his first Royal Rumble match in January 2007, in doing so becoming the first man to enter the Rumble at number 30 and win the match, after lastly eliminating Shawn Michaels.[170] On the February 5 edition of Raw, Undertaker elected to face World Heavyweight Champion Batista at WrestleMania 23, before attacking him with the chokeslam.[171] At No Way Out, Undertaker and Batista reluctantly teamed together to challenge John Cena and Shawn Michaels for the World Tag Team Championship, but failed to win after Batista gained revenge on Undertaker by hitting him with a spinebuster, allowing Cena to pin him.[172] At WrestleMania 23, Undertaker defeated Batista to win his first World Heavyweight Championship and extend his Streak to 15–0.[173] Undertaker faced Batista in a rematch at Backlash, this time in a Last Man Standing match. The match ended in a draw after neither man got to their feet by the referee's count of ten, meaning The Undertaker retained the championship.[174] The Undertaker and Batista then fought once again in a steel cage match on the May 11 edition of SmackDown! that also ended in a draw when both men's feet touched the floor at the same time. After the match, Mark Henry made his return by assaulting an already battered Undertaker, after which Edge ran to the ring and cashed in his Money in the Bank briefcase, forcing Undertaker into a second title defense. Although he kicked out of two quick pin attempts, Undertaker was pinned by Edge after two spears and lost the World Heavyweight Championship.[175] After this match, Undertaker took time off due to a torn right biceps.[176]

The Undertaker after he defeated Edge at WrestleMania XXIV

During his rehabilitation, Henry bragged about his assault on The Undertaker, until vignettes began playing that promoted The Undertaker's return. The Undertaker returned at Unforgiven on September 16, defeating Henry.[177] Batista and The Undertaker reignited their feud at Cyber Sunday with the fans choosing the special guest referee to be Stone Cold Steve Austin, however, Batista retained the World Heavyweight Championship.[178] They battled again inside Hell in a Cell at Survivor Series, where Edge returned and interfered to help Batista retain the World Heavyweight Championship.[179] In response to this, The Undertaker delivered a Tombstone Piledriver to General Manager Vickie Guerrero on the November 23 edition of SmackDown!, sending her to the hospital. Returning assistant-General Manager Theodore Long declared a triple threat match for the title between the three men at Armageddon, which Edge won after interference from The Major Brothers.[180]

At the 2008 Royal Rumble, The Undertaker competed in the Royal Rumble match itself, entering at number 1, but eliminated by Shawn Michaels after lasting for most of the bout.[181] At No Way Out, The Undertaker defeated Batista, Finlay, The Great Khali, MVP and Big Daddy V in the SmackDown Elimination Chamber match to become the number one contender for Edge's World Heavyweight Championship at WrestleMania XXIV.[182] At WrestleMania, The Undertaker defeated Edge with the Hell's Gate submission hold to win his second World Heavyweight Championship in what was his 16th WrestleMania win.[183] In a WrestleMania rematch, The Undertaker defeated Edge once again at Backlash to retain the World Heavyweight Championship.[184] Vickie Guerrero then banned The Undertaker's Hell's Gate submission hold and stripped him of the title on the May 2 edition of SmackDown.[185] The Undertaker battled Edge for the vacant title at Judgment Day, which he won by countout. Guerrero ordered that the title remain vacant, because titles could not change hands in this way.[186] Edge and The Undertaker faced each other again for the vacant championship at One Night Stand in a Tables, Ladders, and Chairs match, which The Undertaker lost after interference from La Familia. As a result of the stipulation, Undertaker was forced to leave WWE.[187]

The Undertaker, after defeating Shawn Michaels at WrestleMania 25

On the July 25 edition of SmackDown, Vickie Guerrero reinstated The Undertaker and scheduled Edge to face him at SummerSlam inside Hell in a Cell,[188] which The Undertaker won. After the match, The Undertaker chokeslammed Edge from the top of a ladder and through the ring canvas.[189] Following this match, Guerrero tried making a peace offering with The Undertaker on SmackDown by apologizing, but The Undertaker told her that he was not the forgiving kind. At Unforgiven, as The Undertaker approached the ring to "take Guerrero's soul" and seal her in a casket, Big Show, who appeared at first to be aiding The Undertaker ended up assaulting him.[190] Resulting from that, The Undertaker and Big Show faced each other in a match at No Mercy, where Big Show won by knockout.[191] At Cyber Sunday, The Undertaker defeated Big Show in a Last Man Standing match after choking him out with Hell's Gate.[192] At the same time, The Undertaker was engaged in a short feud with Jeff Hardy, who interfered during his match with Vladimir Kozlov on the November 7 edition of SmackDown. Hardy defeated The Undertaker in an Extreme Rules match the following week on SmackDown due to interference from Big Show. The Undertaker then went on to defeat Big Show in a casket match at Survivor Series and again in a steel cage match by submission on the December 5 edition of SmackDown to end their feud.[193] At No Way Out, The Undertaker was part of the WWE Championship Elimination Chamber match along with Triple H, Jeff Hardy, Big Show, Vladimir Kozlov and Edge; however, he was unsuccessful at winning the match as he was the runner-up behind Triple H.[194]

In early 2009, The Undertaker began a second chapter to his unresolved feud with Shawn Michaels from the late 1990s, over a decade prior to this point (their tensions gradually increasing in the years immediately preceding this from heated run-ins at the 2007 and 2008 Royal Rumble matches). Their renewed feud by this point was two-dimensional, in part focusing on the wonder of The Undertaker's undefeated WrestleMania Streak in relation to, however, the fact that he had never before defeated Michaels in a singles match, only vice versa.[195] Michaels also made the buildup to their WrestleMania encounter personal, repeatedly demonstrating his Christian objections to the demonic dark side nature of The Undertaker's Deadman gimmick, even creating his own heaven-esque bright side spin-off of what he felt The Undertaker's gimmick should be (Michaels having become a real-life born again Christian by this point in his career).[196][197] The feud culminated in a WrestleMania 25 singles match between the two in which Michaels made a heaven-sent entrance descending from up on high portraying his bright side anti-Deadman, while The Undertaker made a grave-risen entrance emerging from the ground.[197][198][196] After what was widely described as a suspenseful, competitive match, The Undertaker defeated Michaels, thus extending his WrestleMania winning streak to 17–0.[195][199] Their encounter was highly acclaimed by critics and audiences alike and is considered by many to be one of the greatest WrestleMania matches of all time.[196] On the April 24 edition of SmackDown, after losing a match against Big Show by knockout with Big Show taking advantage of The Undertaker's battered neck state from his previous WrestleMania encounter, The Undertaker attacked Big Show. Following this, Undertaker took another hiatus from the WWE.[200]

After a four-month hiatus, The Undertaker returned at SummerSlam in August by attacking CM Punk, who had just won the World Heavyweight Championship from Jeff Hardy in a Tables, Ladders, and Chairs match.[201] At Breaking Point, The Undertaker faced Punk in a submission match. The Undertaker had originally won the match with his Hell's Gate submission hold, but the match was restarted by SmackDown General Manager Theodore Long, who ruled that the ban placed on the move by Vickie Guerrero was still in effect. Punk went on to win the match with his anaconda vise when referee Scott Armstrong called for the bell, despite Undertaker never submitting—a recreation of the Montreal Screwjob, which took place in the same venue in 1997.[202] On the September 25 edition of SmackDown, Theodore Long officially lifted the ban after being released from a casket that The Undertaker had him placed inside of, among a series of other horror-themed mind game tactics.[203] With Long out of the way, the feud between The Undertaker and Punk pressed on and at Hell in a Cell, Undertaker won the World Heavyweight Championship from him in a Hell in a Cell match.[204] The Undertaker successfully defended the title against CM Punk on the October 23 edition of SmackDown, in a fatal four-way match at Bragging Rights against Punk, Batista and Rey Mysterio and in a triple threat match against Chris Jericho and Big Show at Survivor Series.[205][206] He faced Batista at TLC: Tables, Ladders & Chairs in a chairs match for the championship and won when the match was restarted by Long, after Batista had originally won after utilizing a low blow. The next night on Raw, Undertaker competed in a tournament to crown the 2009 Superstar of the Year, losing to Randy Orton by countout in the first round after a distraction by Orton's protegès Cody Rhodes and Ted DiBiase.[207]

The Undertaker defending the World Heavyweight title at the Royal Rumble in January 2010

After successfully defending the World Heavyweight Championship against Rey Mysterio at the Royal Rumble,[208] The Undertaker lost the championship at the Elimination Chamber pay-per-view. It was also at this event that a notorious shoot incident (non-kayfabe) befell The Undertaker: a pyrotechnics malfunction momentarily engulfed him in flames up to three times during his ring entrance. He was, however, able to continue with his scheduled match that night despite suffering first and second-degree burns on his chest and neck. According to a WWE spokesman, it "looked like a bad sunburn".[209] The Undertaker lost the title to Chris Jericho after interference from Shawn Michaels that night;[210] Jericho has said on multiple occasions that the pyrotechnician responsible for the accident was immediately escorted from the arena and relieved of his employment with WWE, following a threat of violence from Calaway.[211][212] Calaway himself explained that he had previously expressed concerns to the technician regarding the pyro arrangement, but was ignored. He feels he was saved from severe injury by applying water to his hair, and altering his attire from a sleeveless to a sleeved jacket, just minutes before the accident.[213]

The Undertaker then accepted Michaels's rematch offer, after initially declining, at WrestleMania XXVI in a Streak vs. Career match, where Undertaker was victorious and Shawn Michaels was forced to retire. This match also made both The Undertaker and Michaels the first men in WWE history to main event WrestleMania in three different decades (Undertaker main evented WrestleMania 13 and XXIV in 1997 and 2008 and Michaels main evented WrestleMania XII and XIV in 1996 and 1998 and XX and 23 in 2004 and 2007, respectively). After a hiatus (which included wrestling two matches on Raw), he returned to SmackDown on May 28, defeating Rey Mysterio to qualify for a spot at the Fatal 4-Way pay-per-view to compete for the World Heavyweight title.[214] During the Rey Mysterio match, The Undertaker suffered a concussion, broken orbital bone and broken nose; he was visibly bleeding profusely on camera by the end of this match.[215] To cover for the injury, Kane revealed that Undertaker had been found in a vegetative state;[216] Mysterio took his place in the match and won the World Heavyweight Championship. While attempting to learn which wrestler had attacked The Undertaker, Kane defeated Mysterio to win the World Heavyweight Championship. Kane and Mysterio continued to clash as they accused one another of being the assailant behind the mysterious ambush of The Undertaker.[217]

At SummerSlam, The Undertaker returned to confront Kane and Rey Mysterio, only to be attacked with a Tombstone Piledriver by Kane. With Kane revealed as his attacker, the two feuded for the next few months over the World Heavyweight Championship. After losing to Kane in a No Holds Barred match at Night of Champions, Paul Bearer returned as Undertaker's manager on the September 24 edition of SmackDown.[218] However, Bearer turned on him at Hell in a Cell to help Kane win once again in a Hell in a Cell match. The feud ended at Bragging Rights when The Nexus helped Kane defeat Undertaker in a Buried Alive match (the half-brothers final singles match against one another). Undertaker needed surgery for a torn rotator cuff, causing him to be written off.[219]

After the 2011 Royal Rumble, promotional videos began airing, showing The Undertaker entering and standing within a Western-style, dilapidated shack on a rainy desert in Death Valley, The Undertaker's birthplace. Each promo ended with the date 2–21–11 being "burned into" the screen. On the February 21 edition of Raw, The Undertaker returned, but before he could speak, Triple H also returned and confronted him. The two challenged each other to a match at WrestleMania XXVII, which was later made a No Holds Barred match and which The Undertaker won by submission. However, he had to be carried away from the ring on a stretcher.[220] Following WrestleMania XXVII in 2011, The Undertaker would take on a more part-time role within the company; he would not have another match on Raw or SmackDown until 2013.

Triple H and The Undertaker at WrestleMania XXVIII

On the January 30, 2012, edition of Raw, The Undertaker returned after a nine-month hiatus to confront Triple H.[221] On the February 13 edition of Raw, Triple H refused The Undertaker's challenge for a WrestleMania rematch.[222] After The Undertaker accused Triple H of living in the shadow of Shawn Michaels on the February 20 edition of Raw, Triple H accepted the challenge on the condition that it would be a Hell in a Cell match; Michaels was later inserted as special guest referee in the match. At WrestleMania XXVIII, The Undertaker, while debuting his new look, a mohawk, defeated Triple H to extend his Streak to 20–0. After the match, Undertaker and Michaels carried Triple H to the entrance stage, where the three embraced.[223] Later in 2012, The Undertaker appeared on the 1000th episode of Raw on July 23 to help Kane, who had been confronted by Jinder Mahal, Curt Hawkins, Tyler Reks, Hunico, Camacho and Drew McIntyre. The Brothers of Destruction overcame and dominated the six other wrestlers.[224][225]

The Undertaker's next television appearance was on Old School Raw on March 4, 2013, where he opened the show by performing his signature entrance. CM Punk, Randy Orton, Big Show and Sheamus fought in a fatal four-way match to determine who would face him at WrestleMania 29, which Punk won.[226] After the real-life death of Paul Bearer on March 5, 2013, a storyline involving Punk regularly spiting The Undertaker through displays of flippancy and disrespect towards Bearer's death began.[227] Punk interrupted The Undertaker's ceremony to honor Bearer on Raw, stealing the trademark urn and later using it to attack Kane, humiliate The Brothers of Destruction and mock Bearer.[228][229] Undertaker defeated Punk at WrestleMania 29 to extend his Streak to 21–0 and then took back the urn.[230] The following night on Raw, Undertaker came out to pay his respects to Bearer, but was interrupted by The Shield, who attempted to attack Undertaker before Kane and Daniel Bryan made the save.[231] Undertaker would wrestle his final Raw match (his first since 2010) on the April 22 edition, teaming with Kane and Bryan against The Shield in a losing effort.[232] Four days later, he wrestled his final SmackDown match (also his first since 2010), defeating Shield member Dean Ambrose by submission. Afterward, Undertaker was attacked by Ambrose and the rest of The Shield, who performed a triple powerbomb through the broadcast table on him.[233]

The Undertaker approaching the ring at WrestleMania XXX in 2014

On the February 24, 2014, edition of Raw, The Undertaker returned to confront Brock Lesnar and accepted his challenge for a match at WrestleMania XXX.[234] After 25 minutes and three F-5s, Lesnar won the match at WrestleMania by pinfall, ending The Undertaker's Streak in what was described as "the most shocking result in WWE history".[235] Following the match, Undertaker was hospitalized with a severe concussion which he suffered in the first minutes of the match.[236] In a December 2014 interview, Vince McMahon confirmed that it was his final decision to have Lesnar end The Streak and that The Undertaker was initially shocked at the decision. McMahon justified his decision that it would significantly enhance Lesnar's formidability to set up the next WrestleMania event and that there were no other viable candidates to fill Lesnar's role.[237] In 2014, The Undertaker was also offered to be inducted into the WWE Hall of Fame, but he declined the offer, feeling it wasn't time yet.[238]

The Undertaker in the ring at WrestleMania 31 in 2015

In February 2015, Bray Wyatt began a series of cryptic promos which led to Fastlane, where Wyatt challenged Undertaker to a match at WrestleMania 31, which Undertaker accepted.[239][240] At WrestleMania, Undertaker defeated Wyatt after two Tombstone Piledrivers.[241]

At Battleground in July, Undertaker made his return by attacking Brock Lesnar as Lesnar was on the verge of defeating Seth Rollins during his WWE World Heavyweight Championship match, which caused the match to end in a disqualification win for Lesnar.[242] The next night on Raw, Undertaker explained his actions as revenge, not against Lesnar breaking The Streak, but rather the constant taunting he allowed Paul Heyman to engage in. Later that night, after Undertaker and Lesnar brawled throughout the arena and had to be separated, a rematch was scheduled for SummerSlam in August, where Undertaker controversially defeated Lesnar. Lesnar put Undertaker in a kimura lock and the timekeeper rang the bell after seeing The Undertaker supposedly indicating submission, but since the referee had not seen a submission and never stopped the match, the match continued. The confusion allowed Undertaker to surprise Lesnar with a low blow and apply Hell's Gate, in which Lesnar passed out.[243] At Hell in a Cell, The Undertaker was defeated by Lesnar in a Hell in a Cell match after Lesnar hit him with his own low blow, returning the favor, and executing what was his third F-5 of the match.[244]

While the crowd gave Undertaker an ovation after his loss to Lesnar, he was attacked and captured by The Wyatt Family (Bray Wyatt, Luke Harper, Erick Rowan and Braun Strowman), who carried him away from the ring.[245] After ambushing and capturing Kane the next night on Raw, Wyatt explained that he had claimed their souls and stole their demonic powers.[246] The Brothers of Destruction returned on the November 9 edition of Raw and attacked The Wyatt Family, setting up a tag team match at Survivor Series, which honored Undertaker's 25 years in WWE.[247] At Survivor Series on November 22, The Brothers of Destruction defeated Wyatt and Harper.[248]

On the February 22, 2016, edition of Raw, Vince McMahon placed his son Shane McMahon, who returned to WWE for the first time since 2009, in a Hell in a Cell match at WrestleMania 32 against The Undertaker with the stipulation that if Shane won, he would gain control of Raw.[249] Vince later decided that should The Undertaker lose the match against Shane, it would be his final match at WrestleMania.[250] After weeks of random physical confrontations and mind games exchanged between the pair, Undertaker defeated Shane McMahon at WrestleMania 32.[251] The Undertaker would not appear again until the 900th episode of SmackDown on November 15, issuing a threat to Team SmackDown if they failed to defeat Team Raw at the upcoming Survivor Series pay-per-view.[252]

The Undertaker in April 2018

The Undertaker then appeared on the January 9, 2017, edition of Raw, where he announced his participation in the Royal Rumble match and said he was a free agent.[253] The Undertaker appeared on the January 23 edition of Raw, confronting Brock Lesnar and Goldberg.[254] During the Royal Rumble on January 29, The Undertaker entered at number 29, eliminating Goldberg, The Miz, Baron Corbin and Sami Zayn, before being eliminated by the number 30 entrant, Roman Reigns.[255] Undertaker returned on the March 6 edition of Raw and performed a chokeslam on Reigns.[256] This led to a No Holds Barred match between Undertaker and Reigns at WrestleMania 33,[257] in which Undertaker lost to Reigns after five spears in his fourth WrestleMania main event.[258] After the match, Undertaker left his gloves, coat and hat in the center of the ring before slowly making his exit.[259]

Undertaker took part in the Raw 25 Years edition of Raw on January 22, 2018, his first post-WrestleMania 33 appearance.[260] In the months prior to WrestleMania 34, John Cena challenged The Undertaker to a singles match. At WrestleMania, after Elias confronted Cena and was beaten down, The Undertaker's hat and coat appeared in the center of the ring—where he had left them the previous year—and was struck by lightning. The Undertaker then appeared and beat Cena in an impromptu three-minute squash match.[261] Three weeks later, The Undertaker defeated Rusev at WWE's Greatest Royal Rumble event in a casket match.[262]

At Super Show-Down in Australia on October 6, The Undertaker faced Triple H in a no disqualification match billed as the "Last Time Ever"; they were accompanied by Kane and Shawn Michaels, respectively. The Undertaker lost the match after interference from Michaels. After the match, the four men shook hands as a sign of respect, however, Undertaker and Kane would follow this by attacking them.[263] As a result, the duos reunited their respective tag teams—The Brothers of Destruction and D-Generation X—and faced each other at Crown Jewel on November 2, where The Undertaker and Kane lost (the Brothers of Destruction's final match as a tag team combination).[264]

On April 8, 2019, edition of Raw, the night after WrestleMania 35—the first WrestleMania in 19 years without his involvement—The Undertaker made his next appearance, interrupting and attacking Elias during one of his musical performances.[265] The Undertaker made his return to the ring to face Goldberg at Super ShowDown in Saudi Arabia on June 7, defeating him in the main event of the night in what was their first match against each other.[266] On the June 24, 2019, edition of Raw, during a handicap match in which Roman Reigns was dominated by Shane McMahon and Drew McIntyre, The Undertaker suddenly appeared and attacked McMahon and McIntyre. It was later announced that Undertaker and Reigns would face McMahon and McIntyre in a No Holds Barred tag team match at Extreme Rules. At Extreme Rules, Undertaker and Reigns won.[267]

The Undertaker returned at Super ShowDown in Saudi Arabia on February 27, 2020, as a surprise replacement in a gauntlet match. He entered the match last, replacing Rey Mysterio and defeating AJ Styles to win the Tuwaiq Mountain Trophy.[268] On the March 2, 2020, edition of Raw while Styles was facing Aleister Black, he [Styles] taunted The Undertaker. At Elimination Chamber while Styles was facing Black in a rematch with a no-disqualification stipulation, The Undertaker made yet another surprise appearance thwarting his efforts, interfering in the match with an attack on Styles.[269] The following night on Raw, Styles challenged The Undertaker to a match at WrestleMania 36.[270] Over the following weeks that led up to WrestleMania, a resentful Styles made unprecedented efforts to expose The Undertaker, going so far as departing from bashing his Deadman gimmick, instead taking to a metafiction form of bashing Calaway himself. The feud saw Styles solely referring to The Undertaker by his real name, Mark Calaway. In this manner, Styles leveled zingers and criticisms at him in relation to his age cringingly catching up with him, as well as hurling brazen insults at Calaway in relation to his wife, Michelle McCool. In response, The Undertaker cut promos of ominous warning against Styles in which for the first time in years, he broke from the Deadman gimmick by presenting as himself out of character. In doing so, elements of his American Badass gimmick were reflected with Calaway making appearances in his biker gear. At WrestleMania 36, The Undertaker presented his third and final identity, "The Unholy Trinity," a combination of The Deadman, American Badass, and himself as Mark Calaway, this blend allowing him to trash talk Styles over real life matters during their encounter, while also able to maintain his superhuman horror capabilities.[271] In what was subsequently learned to be The Undertaker's final match, he and Styles fought absent of a live audience in a cemetery at a secluded rural locale, competing in what was a cinematic, narrative-heavy brawl. This stipulation match—issued as a challenge by The Undertaker and connected to his character—was the first ever "Boneyard match". (While the novel nature of this match was heavily influenced by the COVID-19 pandemic at its most acute during this time period, even standard matches of this wrestling era were narrative-heavy in order to counter awkward silence of audience absence, which was enforced by then pandemic laws). Despite the assistance of Gallows and Anderson, The Undertaker buried Styles in the grave to win this bout and ride off on motorcycle into the sunset,[272] scoring his 25th WrestleMania victory to complete his professional wrestling career.[273]

On June 21, 2020, in the final episode of the Undertaker: The Last Ride documentary, The Undertaker announced his retirement from the professional wrestling industry.[8] Later on that November, he confirmed that he was "officially retired" in an interview.[9] Many wrestlers and other public figures paid tribute to him on their social media pages.[274] Madison Square Garden, regarded as the most famous venue in professional wrestling, also paid tribute to him.[275]

The Undertaker, wearing his trademark mortician trench coat and stetson hat, made an appearance at the conclusion of the Survivor Series event on November 22, 2020. The event is dedicated to him, commemorating thirty years from that time since his WWE debut. There, he reiterated that his career had been completed, giving an emotional farewell speech which ended in typical Undertaker fashion: "My time has come to let The Undertaker Rest in Peace."[276][10] A ten-bell salute was also given for The Undertaker character as he did his traditional take-the-knee pose, and a holographic image of Paul Bearer, the Undertaker's former manager, was projected in the ring.[277]

On February 18, 2022, it was announced that The Undertaker would be inducted into the WWE Hall of Fame class of 2022.[278] The news was responded to with extensive praise from WWE fans, the professional wrestling community and media outlets alike.[279] In the weeks following the announcement, media outlets observed that many WWE fans had advocated for the idea of a one-man show Hall of Fame dedicated to The Undertaker alone, reasoning that his legend status in the company would warrant such an honor.[280] The solo dedication was also publicly endorsed by WWE Hall of Famer Bubba Ray Dudley, sharing as well of his opinion that such an event would be an entertainment draw and sell out the arena[281] (Vader, however, was later revealed to be a posthumous second inductee of the class of 2022 Hall of Fame).[282] On March 3, 2022, then WWE Chairman and CEO Vince McMahon made a rare media appearance on The Pat McAfee Show, announcing that he would be The Undertaker's WWE Hall of Fame inductor. In praising The Undertaker both inside and outside of character in a heartfelt message, McMahon elaborated that this induction will be one of the most difficult endeavors of his life because of his longtime history with The Undertaker, what they've been through together, and how close they've been behind the scenes.[283] Reacting to the heavily publicized announcement from McMahon, The Undertaker issued a Twitter response later on that same day, which read:

After over 30 years of long roads traveled, countless hours of TV, and one hell of a ride together… couldn’t think of anyone better to put me in the #WWEHOF than @VinceMcMahon. One final ride together, old-timer!!![284]

— The Undertaker

On April 1, 2022, The Undertaker was formally inducted into the WWE Hall of Fame at the American Airlines Center.[285] As his induction, Calaway made a 137-minute speech that opened with a 10-minute, emotional standing ovation from the live audience, bringing Calaway to tears. Calaway's acceptance speech, hailed by media outlets as matchless and beyond compare, was motivational and shared his collection of self-reflections and life philosophies for success. In making his speech, he stood before several genres of his Deadman character, through the varying costumes displayed on mannequins.[286] Later that same weekend, Calaway made appearances on the entrance stage on both nights of WrestleMania.

The Undertaker, as his Deadman character, preparing to supernaturally trigger lights back to the arena from raised arms as part of his entrance

Under his undead, funereal, and macabre horror-themed gimmick, in which The Undertaker is subtitled "The Deadman", he routinely took to alarmist tactics to disrupt the focus and confidence of his rivals.[287][288] Often, these alarmist tactics were morbid and applied the use of props that reflected demise as the consequence of a wrestling match against him: caskets (sometimes personalizing casket designs to represent his opponents),[289][70] body bags,[290] corpse-like effigies,[288] cemeteries,[290] hearses.[291] To that end, the gimmick evoked funerals and death down to subtle details, such as in the character's birthplace of Death Valley, catch phrase of "Rest in Peace", signature finishing maneuver of the Tombstone Piledriver, a wrestling pin that had the opponent resemble a corpse with their arms crossed over their chest, etc.[291][292] Adding to his many effects of treating his wrestling matches as funeral services, The Undertaker frequently served a list of specialized matches that were personalized to his Deadman gimmick: Casket Match, Body Bag Match, Buried Alive Match, Last Ride Match, Hell in a Cell, Boneyard Match, etc.[293][294][295]

Filled with bells and whistles, The Undertaker's godlike superhuman presence and indignation were signaled by funeral tolls, settings of pitch-black darkness and blue/purple semidarkness, flickering lights, hazy fog, thunder, lightning strikes, and other bone-chilling scenes and sound activity.[296][297][298] Portrayed as miraculously resilient to destruction,[299] The Undertaker yielded numerous resurrections,[15] which sometimes gave way to reincarnations of his Deadman gimmick. While maintaining his general character premise as death personified with accompanying alarmist tactics throughout all sagas of the Deadman,[300][301] each incarnation took on its own distinct appearance and characterization. For example, some Deadman incarnations were unearthly and zombie-like while others were Goth and comparatively more human.[302]

The earliest of The Undertaker's Deadman incarnations (nicknamed in external media as "The Old West Mortician" to distinguish from his other Deadman incarnations[49]) depicted him as a menacing derivative of the Wild West undertakers in television westerns.[50] In his own rendition, he was garbed in a black trench coat; gray-striped tie; black-ribboned, black stetson hat; gray boot spats; and gray gloves[303] (black gloves for first few appearances before gray).[46] However, most of The Undertaker's Deadman character development (sleeve tattoos, longer/straightened/black hair, purple/blue color representation, elements of thunder and lightning, etc.) would not surface until his first reincarnation into what was his rebirthed Deadman variation, lasting from SummerSlam 94' (resurrection from a death angle with Yokozuna) through Buried Alive: In Your House (The Undertaker buried alive by Mankind and numerous other WWF heel wrestlers).[77] In these initial zombie-like incarnations of his gimmick, he was portrayed as impervious to pain, something accomplished by Calaway not selling his opponents' attacks. Among the many ways this was showcased was The Undertaker's maneuver of raising up from a taken down supine position into a high Fowler's position, dubbed "the sit-up" (often accompanied by his sharp hissing sound).[291]

Beginning early on, The Undertaker's persona was complemented with histrionically spooky, wailing manager Paul Bearer, introduced to represent and guide The Deadman.[304] Playing a key role, Bearer used an urn to transmit mysterious powers to The Undertaker that had supernatural healing effects on him during combat.[305] Also linked to The Undertaker's Deadman gimmick were the druids–a team of mysterious, incognito cult-like members, completely disguised in black hooded clergy robes.[306] A mysterious choir chanting sounded whenever the druids presented.[307] The druids typically appeared for the purposes of removing The Undertaker where he had seemingly been extinguished by his enemies (as opposed to EMTs or medical personnel used for the rest of WWF/E talent). The druids were also seen reproducing The Undertaker in recovered, wrathful states to those same enemies who were thought to have extinguished him.[307][308]

The Undertaker took to many trademarked idiosyncrasies and themes, including a stylized throat-slashing gesture,[309] grimacing facial expressions fit with eyeballs rolled back so that only the whites of his eyes displayed,[310] backwards hair-whips so as to expose his ominous facial expressions,[311] fixed stares on adversaries,[310] protruding tongue displays, jolting of his head with a fury so that it faced the direction of his antagonists,[312] his celebratory take-the-knee pose,[313] sonorous vocalizations,[314] collectively labeling his fanbase as "Creatures of the Night",[315] voice of God-like promos in which things were interrupted with dimmed lights and thunder while The Undertaker's communications were heard booming throughout the arena with no physical trace of him;[316] messages filled with death threats of a deeply posthumous insight into impending corpse decomposition, maggot feasting, unsouling and so on.[317] A main attraction of the Deadman gimmick, The Undertaker mesmerized his opponents and viewers alike through elaborately "bone-chilling" entrances.[318] The character's godlike powers were routinely put on display in these moments, triggering lights back to the arena either gradually or suddenly dependent on his either slowly or abruptly raised arms.[296] During the vast majority of his wrestling career as the Deadman, The Undertaker used an extended remix of Frédéric Chopin's Funeral March as his theme music.[319] WWF Composer Jim Johnston embellished on the Chopin march, using the historic melody as a pre- and post-chorus to a main chorus of bell tolls, along with an original transition section to the song of a slow, lugubrious instrumental feel.[320] Of his entrances, Calaway has stated, "When that gong went off, that was go time. The music fit the character. That's the key element of it: the end is at hand for whoever's going to be standing in that ring waiting for me to come down. That was the mindset behind the gong. And the music was just doom and gloom, you knew what was coming."[321]

After a hiatus, Calaway made a return in 2000 in which he expanded on The Undertaker gimmick with a human form of the character. Under the character's alter ego, he is a semifictional smack-talking, redneck biker, thoroughly absent of his fully fictional Deadman zombie-like traits and wizardry.[122][119] In performing this alternate identity, he rode to the ring on motorcycles, chewed tobacco, donned cargo garments and/or denim, printed shirts, and sporty fashion accessories (sunglasses, necklaces, bandanas).[120][322] His theme music was replaced with popular rock songs of the time, initially Kid Rock's "American Bad Ass" (from which The Undertaker's subtitle used to refer to this second identity derived), and eventually Limp Bizkit's "Rollin' (Air Raid Vehicle)".[323] His American Badass catch phrases, such as threats of “I'll make you famous” or references to the wrestling ring as his “yard”, became popular during this era. According to Bruce Prichard, Calaway requested this metamorphosis of character since he wanted to be "the biker–he wanted to be the guy that he is in everyday life".[324]

While explained off-screen for the above reason years later, Calaway's sudden appearance as American Badass Undertaker after hiatus in which he left off as Deadman Undertaker was never explained within WWE storylines or the WWE's fictional universe. Rather, the expectation was for fans to just go with it.[122] This transition lasted 3 and a half years until 2004 when The Undertaker resurrected his Deadman identity in hybrid form—residual features of his American Badass identity remaining. Among subtle details left over from his biker identity were his in-ring MMA style between his stances, strikes, and submissions; penchant to sporadically lower his tank top for a barechested appearance; celebrating victories with an arm-raised fist; etc.[142] This hybrid Deadman (Deadman incarnation most closely based on Calaway himself) would last many years and for the remainder of The Undertaker's professional wrestling career, excluding his final wrestling match. For The Undertaker's final encounter, a Boneyard Match at WrestleMania 36 in 2020, he introduced a three-dimensional identity that brought all of his identities into one, dubbed "The Unholy Trinity:" a mix of his Deadman identity, American Badass identity, and his natural and genuine identity as Mark Calaway.[271]

The Undertaker generated many nicknames from commentators and spectators alike throughout the course of his active wrestling career, some of those names more associated with his Deadman Undertaker identity, including "The Grim Reaper" (variants of this used were "The Reaper" and "The Reaper of Wayward Souls"),[325] "The Demon of Death Valley",[326] "The Man from the Dark Side",[327] "The Prince of Darkness",[328] "The Lord of Darkness".[329] He also generated nicknames associated with his American Badass Undertaker identity, including "Big Evil" (used in reference to his American Badass heel side),[330] "Booger Red", etc.[331] Some of his nicknames were not identity specific but used for The Undertaker gimmick in general, such as "The Phenom".[329][332]

The Undertaker gimmick has a dark and disturbed family backstory which involves him intentionally burning down his family funeral home as a teenager, resulting in the deaths of his parents and purportedly a brother of his as well. The Undertaker initially denied his then ex-manager Paul Bearer's charges of him committing the arson murder of his family (The Undertaker would not confess to these intentional acts of arson until a year and a half later from his initial denials, in latter 1998). The Undertaker, instead, laid the charges against his younger brother of whom he thought long dead from the incident, describing him as a "pyromaniac". This led to Bearer's shocking warnings to proof in the form of the brother, "Kane", as alive and well.[92] In late 1997 at In Your House Badd Blood, Bearer unleashed a vengeful Kane: the fire-personified, juggernaut half-brother of The Undertaker, who was fit with a mask to conceal the scarring from The Undertaker's arson.[92] In what became a fickle sibling relationship with Bearer (later revealed to be Kane's father) only adding to the pendulum and complexities, The Undertaker and Kane went back and forth from one extreme to the other, feuding barbarically at points and yet teaming as The Brothers of Destruction at other points.[92] In the duo's final feud in late 2009 through 2010, Kane emerged victorious in all of their matches.

The Undertaker's wrestling performance and move set were carried out with significant amounts of character-driven physical theatre and kinesics. In keeping with his Deadman routine for example, The Undertaker was forbiddingly slow and measured in much of his maneuvering and offense.[291] Taking his opponents and audience by surprise, however, he combined his slow, measured physicality with wrestling moves and action uncharacteristic of a wrestler of his vast height and weight.[52][333] Not limited to just ground offense and power moves, The Undertaker was conspicuously aerial, swift, agile, loose-limbed and animated in the other half of his wrestling style and move set:[333] flying clotheslines,[334] guillotine leg drops,[335] running DDTs,[336] ability to land on his feet poised and motionless if thrown from the ring,[310] over-the-top-rope suicide dives[333][337] (on one occasion, over the top rope and combined active flames during an Inferno match at In Your House Unforgiven), etc. During matches, The Undertaker would also pay homage to Don Jardine by performing an arm twist ropewalk chop, dubbed "Old School."[338]

Most famed for his Deadman Undertaker identity in particular, the role won Calaway the Wrestling Observer Newsletter awards for Best Gimmick a record-setting 5 years in a row (1990–1994). Calaway was highly protective of his Deadman public image: for the vast majority of his career while performing the gimmick, he was so private that he wasn't seen outside of character in the media. Calaway's approach of presenting only in character publicly was done in order to maintain the mystique of the Deadman and facilitate disbelief suspension.[339] However, during the last few years of his wrestling career, he allowed himself to be seen out of character, giving interviews as Mark Calaway and filming a documentary called The Last Ride.[340]

The Undertaker has been named one of the greatest wrestlers of all time.[341] He was voted the greatest WWE wrestler ever in a 2013 Digital Spy poll.[342] In naming him the second greatest wrestler ever, IGN described The Undertaker as, "one of the most respected wrestlers, and characters, in the business; treated with actual reverence. Like a cherished, invaluable artifact".[343] Luis Paez-Pumar of Complex wrote that The Undertaker character is "easily the best gimmick in the history of professional wrestling".[344] Luke Winkie of Sports Illustrated listed The Undertaker as the fifth greatest wrestler of all time.[345] His consecutive matches with Shawn Michaels at WrestleManias XXV and XXVI were met with critical acclaim, with both matches winning the Pro Wrestling Illustrated and Wrestling Observer Newsletter awards for Match of the Year in 2009 and 2010 respectively.[346][347]

Wrestler Big Show named The Undertaker as the greatest professional wrestler of all time,[348] while Mark Henry and WWE chairman Vince McMahon have called him their favorite.[349][350] WWE Hall of Famer and former company executive, Jim Ross, said: "Without question, The Undertaker is the greatest big man in the history of wrestling... There is no greater WWE star ever than The Undertaker".[351]

Guinness World Records Gamer's Edition recognized Undertaker as having the most consecutive victories at WrestleMania in 2016.[352] In November 2015, Telegraph journalist Tom Fordy called The Undertaker "the world's greatest sportsman".[353]

Undertaker's Deadman character in particular has been praised as one of the best in professional wrestling. He received the Wrestling Observer Newsletter's Best Gimmick award from 1990 to 1994. Tim Friorvant of ESPN named The Undertaker "a character that has been a cornerstone of the WWE for more than three decades".[354] Shawn Valentino of Pro Wrestling Torch said "The Undertaker may have been the greatest character in the history of professional wrestling".[355]

A 12-minute match between The Undertaker and Stone Cold Steve Austin drew a 9.5 rating on June 28, 1999. It stands as the highest-rated segment in Raw history.[356]

The Undertaker walks away from the ring after The Streak was broken at WrestleMania XXX in April 2014

In contrast to the high praise The Undertaker received during the vast majority of his professional wrestling career, he was heavily criticized for continuing to perform throughout the latter part of his wrestling career, particularly after his first defeat at WrestleMania. Calaway would later reveal that after suffering a severe concussion in his WrestleMania match against Lesnar, he lost his confidence.[357] At WrestleMania 33, after his second defeat against Roman Reigns, Luis Paez-Pumar of Rolling Stone said that The Undertaker "should have retired when The Streak was broken" but "lived on to pass the rub on to Reigns in the sloppiest, saddest manner possible".[358] The Undertaker himself said he was disappointed by his performance against Reigns.[359] After his match against John Cena at WrestleMania 34, IGN posted an article titled "Undertaker's return was awesome, but now he needs to retire".[360] After his match at Crown Jewel in November 2018, Pro Wrestling Torch's Wade Keller wrote that Undertaker looked "brittle"[361] and Jason Powell of Pro Wrestling Dot Net said "they [Undertaker, Kane, Michaels and Triple H] need to accept their limitations, stop pretending they belong in main events, and stop acting like being in these main events isn't stealing the spotlight".[362] His subsequent match with Goldberg at Super ShowDown in June 2019 was also widely pilloried, with Bryan Rose of the Wrestling Observer Newsletter calling it "sad more than anything".[363] In reviewing the show, Dave Meltzer of the same publication wrote that Goldberg "has juice left, while Undertaker doesn't".[364] The Undertaker himself called the match "a disaster" in 2020.[365]

Despite the media criticism, two of The Undertaker's later matches—teaming with Roman Reigns against Drew McIntyre and Shane McMahon at Extreme Rules 2019, as well as his cinematic Boneyard match against AJ Styles at WrestleMania 36—were both widely praised, with many fans and critics alike citing both matches as his best performances in recent years. The former would be ranked #25 on WWE.com's 25 best matches of 2019, and the latter was ranked #1 on WWE.com's 25 best matches of 2020. The Boneyard match would also win WWE's Half-Year Award for best Cinematic Match, as well as winning the Slammy Award for 2020's Match of the Year.[366][367] [9][368][369]