David Letterman

Soon after graduating from Ball State in 1969, Letterman began his career as a radio talk show host on WNTS (AM) and on Indianapolis television station WLWI (which changed its call sign to WTHR in 1976) as an anchor and weatherman. He received some attention for his unpredictable on-air behavior, which included congratulating a tropical storm for being upgraded to a hurricane and predicting hailstones "the size of canned hams."[21] He also occasionally reported the weather and the day's very high and low temps for fictitious cities ("Eight inches of snow in Bingree and surrounding areas"), on another occasion saying that the state border between Indiana and Ohio had been erased when a satellite map accidentally omitted it, attributing it to dirty political dealings. ("The higher-ups have removed the border between Indiana and Ohio, making it one giant state. Personally, I'm against it. I don't know what to do about it.")[22] He also starred in a local kiddie show, made wisecracks as host of a late-night TV show called "Freeze-Dried Movies" (he once acted out a scene from Godzilla using plastic dinosaurs), and hosted a talk show that aired early on Saturday mornings called Clover Power,[23] in which he interviewed 4-H members about their projects.[24]

In 1971, Letterman appeared as a pit road reporter for ABC Sports' tape-delayed coverage of the Indianapolis 500, which was his first nationally telecast appearance (WLWI was the local ABC affiliate at the time).[25] He was initially introduced as Chris Economaki, but this was corrected at the end of the interview (Jim McKay announced his name as Dave Letterman). Letterman interviewed Mario Andretti, who had just crashed out of the race.

Letterman's comedic career took hold at Los Angeles's Comedy Store

In 1975, encouraged by his then-wife Michelle and several of his Sigma Chi fraternity brothers, Letterman moved to Los Angeles, California, with the hope of becoming a comedy writer.[26] He and Michelle packed their belongings in his pickup truck and headed west.[27] As of 2012, he still owned the truck.[28] In Los Angeles, he began performing comedy at The Comedy Store.[29] Jimmie Walker saw him on stage; with an endorsement from George Miller, Letterman joined a group of comedians whom Walker hired to write jokes for his stand-up act, a group that at various times also included Jay Leno, Paul Mooney, Robert Schimmel, Richard Jeni, Louie Anderson, Elayne Boosler, Byron Allen, Jack Handey, and Steve Oedekerk.[29][30]

By the summer of 1977, Letterman was a writer and regular on the six-week summer series The Starland Vocal Band Show, broadcast on CBS.[31] He hosted a 1977 pilot for a game show called The Riddlers[32][33] (which was never picked up), and co-starred in the Barry Levinson-produced comedy special Peeping Times, which aired in January 1978. Later that year, Letterman was a cast member on Mary Tyler Moore's variety show, Mary.[34] He made a guest appearance on Mork & Mindy (as a parody of EST leader Werner Erhard)[35] and appearances on game shows such as The $20,000 Pyramid,[36] The Gong Show, Hollywood Squares, Password Plus,[37] and Liar's Club, as well as the Canadian cooking show Celebrity Cooks (November 1977), talk shows such as 90 Minutes Live (February 24[38] and April 14, 1978),[39] and The Mike Douglas Show (April 3, 1979 and February 7, 1980). He was also screen tested for the lead role in the 1980 film Airplane!, a role that eventually went to Robert Hays.[40]

Letterman's brand of dry, sarcastic humor caught the attention of scouts for The Tonight Show Starring Johnny Carson, and he was soon a regular guest on the show. He became a favorite of Carson and was a regular guest host for the show beginning in 1978. Letterman credits Carson as the person who influenced his career the most.[41]

On June 23, 1980, Letterman was given his own morning comedy show on NBC, The David Letterman Show. It was originally 90 minutes long but was shortened to 60 minutes in August 1980.[42] The show was a critical success, winning two Emmy Awards, but was a ratings disappointment and was canceled, the last show airing October 24, 1980.[43]

Letterman interviewing comedian Jerry Lewis in 1982

NBC kept Letterman on its payroll to try him in a different time slot. Late Night with David Letterman debuted February 1, 1982; the first guest was Bill Murray.[44] Murray went on to become one of Letterman's most recurrent guests, guesting on his later CBS show's celebration of his 30th anniversary in late-night television, which aired January 31, 2012, and on the final CBS show, which aired May 20, 2015. The show ran Monday through Thursday nights at 12:30 a.m. Eastern Time, immediately following The Tonight Show Starring Johnny Carson (a Friday night broadcast was added in June 1987). It was seen as edgy and unpredictable, and soon developed a cult following (particularly among college students). Letterman's reputation as an acerbic interviewer was borne out in verbal sparring matches with Cher[45] (who even called him an "asshole" on the show[46]), Shirley MacLaine,[47] Charles Grodin, and Madonna. The show also featured comedy segments and running characters, in a style heavily influenced by the 1950s and 1960s programs of Steve Allen.[48]

The show often featured quirky, genre-mocking regular features, including "Stupid Pet Tricks"[49] (which had its origins on Letterman's morning show), Stupid Human Tricks,[50] dropping various objects off the roof of a five-story building,[51] demonstrations of unorthodox clothing (such as suits made of Alka-Seltzer,[52] Velcro[53] and suet), a recurring Top 10 list, the Monkey-Cam[54] (and the Audience Cam), a facetious letter-answering segment,[55] several "Film[s] by My Dog Bob" in which a camera was mounted on Letterman's own dog[56] (often with comic results) and Small Town News,[57] all of which moved with Letterman to CBS.

Other episodes included Letterman using a bullhorn to interrupt a live interview on The Today Show on August 19, 1985, announcing that he was the NBC News president Lawrence K. Grossman and that he was not wearing any pants;[58] walking across the hall to Studio 6B, at the time the news studio for WNBC-TV, and interrupting Al Roker's weather segments during Live at Five; and staging "elevator races", complete with commentary by NBC Sports' Bob Costas. In one appearance, in 1982, Andy Kaufman (who was wearing a neck brace) appeared with professional wrestler Jerry Lawler, who slapped and knocked the comedian to the ground (Lawler and Kaufman's friend Bob Zmuda later revealed that the incident was staged).[59]

The Ed Sullivan Theater, where Late Show with David Letterman was recorded

In 1992, Johnny Carson retired and many fans believed that Letterman would become host of The Tonight Show. When NBC instead gave the job to Jay Leno, Letterman departed NBC to host his own late-night show on CBS, opposite The Tonight Show at 11:30 p.m., called the Late Show with David Letterman. The new show debuted on August 30, 1993, and was taped at the historic Ed Sullivan Theater, where Ed Sullivan broadcast his eponymous variety series from 1948 to 1971. For Letterman's arrival, CBS spent $8 million in renovations.[60] CBS also signed Letterman to a three-year, $14 million/year contract,[61] doubling his Late Night salary.

But while the expectation was that Letterman would retain his unique style and sense of humor with the move, Late Show was not an exact replica of his old NBC program. The monologue was lengthened. Paul Shaffer and the World's Most Dangerous Band followed Letterman to CBS, but they added a brass section and were rebranded the CBS Orchestra (at Shaffer's request); a small band had been mandated by Carson while Letterman occupied the 12:30 slot. Additionally, because of intellectual property disagreements, Letterman was unable to import many of his Late Night segments verbatim,[62] but he sidestepped this problem by simply renaming them (the "Top Ten List" became the "Late Show Top Ten", "Viewer Mail" became the "CBS Mailbag", etc.). Time magazine wrote, "Letterman's innovation ... gained power from its rigorous formalism"; as his biographer Jason Zinoman puts it, he was "a fascinatingly disgruntled eccentric trapped inside a more traditional talk show."[63]

The Late Show's main competitor was NBC's The Tonight Show, which Jay Leno hosted for 22 years from 1992 to 2014, except from June 1, 2009, to January 22, 2010, when Conan O'Brien hosted. In 1993 and 1994, the Late Show consistently gained higher ratings than The Tonight Show. But in 1995, ratings dipped and Leno's show consistently beat Letterman's in the ratings from the time that Hugh Grant came on Leno's show after Grant's arrest for soliciting a prostitute.[64]

Leno typically attracted about five million nightly viewers between 1999 and 2009. The Late Show lost nearly half its audience during its competition with Leno, attracting 7.1 million viewers nightly in its 1993–94 season and about 3.8 million per night as of Leno's departure in 2009.[65] In the final months of his first stint as host of The Tonight Show, Leno beat Letterman in the ratings by a 1.3 million-viewer margin (5.2 million to 3.9 million), and Nightline and the Late Show were virtually tied.[66] Once O'Brien took over Tonight, Letterman closed the gap in the ratings.[67][68][69] O'Brien initially drove the median age of Tonight Show viewers from 55 to 45, with most older viewers opting to watch the Late Show instead.[70] After Leno returned to The Tonight Show, Leno regained his lead.[71]

Letterman's shows have garnered both critical and industry praise, receiving 67 Emmy Award nominations, winning 12 times in his first 20 years in late night television. From 1993 to 2009, Letterman ranked higher than Leno in the annual Harris Poll of Nation's Favorite TV Personality 12 times.[72] For example, in 2003 and 2004 Letterman ranked second in that poll, behind only Oprah Winfrey, a year that Leno was ranked fifth.[73] Leno was higher than Letterman on that poll three times during the same period, in 1998, 2007, and 2008.[72]

On March 27, 1995, Letterman hosted the 67th Academy Awards ceremony. Critics blasted what they deemed his poor performance, noting that his irreverent style undermined the traditional importance and glamor of the event.[74] In a joke about their unusual names (inspired by a celebrated comic essay in The New Yorker, "Yma Dream" by Thomas Meehan), he started off by introducing Uma Thurman to Oprah Winfrey, and then both of them to Keanu Reeves: "Oprah...Uma. Uma...Oprah," "Have you kids met Keanu?" This and many of his other jokes fell flat.[74] Although Letterman attracted the highest ratings to the annual telecast since 1983, many felt that the bad publicity he generated caused a decline in the Late Show's ratings.[75]

Letterman recycled the apparent debacle into a long-running gag. On his first show after the Oscars, he joked, "Looking back, I had no idea that thing was being televised." He lampooned his stint two years later, during Billy Crystal's opening Oscar skit, which also parodied the plane-crashing scenes from that year's chief nominated film, The English Patient.

For years afterward, Letterman recounted his hosting the Oscars, although the Academy of Motion Picture Arts and Sciences continued to hold Letterman in high regard and invited him to host the Oscars again.[76][77] On September 7, 2010, he made an appearance on the premiere of the 14th season of The View, and confirmed that he had been considered for hosting again.

On January 14, 2000, a routine check-up revealed that an artery in Letterman's heart was severely obstructed. He was rushed to emergency surgery for a quintuple bypass at New York Presbyterian Hospital.[78] During the initial weeks of his recovery, reruns of the Late Show were shown and introduced by friends of Letterman including Norm Macdonald, Drew Barrymore,[69] Ray Romano, Robin Williams, Bonnie Hunt, Megan Mullally, Bill Murray, Regis Philbin, Charles Grodin, Nathan Lane, Julia Roberts,[69] Bruce Willis, Jerry Seinfeld, Martin Short, Steven Seagal, Hillary Clinton, Danny DeVito, Steve Martin, and Sarah Jessica Parker.

Subsequently, while still recovering from surgery, Letterman revived the late-night talk show tradition of "guest hosts" that had virtually disappeared on network television during the 1990s, allowing Bill Cosby, Kathie Lee Gifford, Dana Carvey, Janeane Garofalo, and others to host new episodes of the Late Show. Upon his return to the show on February 21, 2000, Letterman brought all but one of the doctors and nurses on stage who had participated in his surgery and recovery (with extra teasing of a nurse who had given him bed baths—"This woman gave me a bath!"),[79] including Dr. O. Wayne Isom and physician Louis Aronne, who frequently appeared on the show. In a show of emotion, Letterman was nearly in tears as he thanked the health care team with the words "These are the people who saved my life!"[80] The episode earned an Emmy nomination.

For a number of episodes, Letterman continued to crack jokes about his bypass, including saying, "Bypass surgery: it's when doctors surgically create new blood flow to your heart. A bypass is what happened to me when I didn't get The Tonight Show! It's a whole different thing." In a later running gag, he lobbied Indiana to rename the freeway circling Indianapolis (I-465) "The David Letterman Bypass". He also featured a montage of faux news coverage of his bypass surgery, which included a clip of Letterman's heart for sale on the Home Shopping Network. Letterman became friends with his doctors and nurses. In 2008, a Rolling Stone interview stated

he hosted a doctor and nurse who'd helped perform the emergency quintuple-bypass heart surgery that saved his life in 2000. 'These are people who were complete strangers when they opened my chest,' he says. 'And now, eight years later, they're among my best friends.'[81]

Additionally, Letterman invited the band Foo Fighters to play "Everlong",[82] introducing them as "my favorite band, playing my favorite song."[83] During Letterman's last show, on which Foo Fighters appeared, Letterman said that Foo Fighters had been in the middle of a South American tour which they canceled to come play on his comeback episode.[84]

Letterman again handed over the reins of the show to several guest hosts (including Bill Cosby, Brad Garrett, Whoopi Goldberg,[85] Elvis Costello,[85] John McEnroe, Vince Vaughn,[85] Will Ferrell,[85] Bonnie Hunt, Luke Wilson, and bandleader Paul Shaffer) in February 2003, when he was diagnosed with a severe case of shingles. Later that year, Letterman made regular use of guest hosts—including Tom Arnold and Kelsey Grammer—for new shows broadcast on Fridays. In March 2007, Adam Sandler, who had been scheduled to be the lead guest, served as a guest host while Letterman was ill with a stomach virus.[86]

Letterman with President Barack Obama in 2009

In March 2002, as Letterman's contract with CBS neared expiration, ABC offered him the time slot for long-running news program Nightline with Ted Koppel. Letterman was interested, as he believed he could never match Leno's ratings at CBS due to Letterman's complaint of weaker lead-ins from the network's late local news programs, but was reluctant to replace Koppel.[87] He addressed his decision to re-sign on the air, stating that he was content at CBS and that he had great respect for Koppel.

On December 4, 2006, CBS revealed that Letterman signed a new contract to host Late Show with David Letterman through the fall of 2010. "I'm thrilled to be continuing on at CBS," said Letterman. "At my age you really don't want to have to learn a new commute."[88] Letterman further joked about the subject by pulling up his right pants leg, revealing a tattoo, presumably temporary, of the ABC logo.

"Thirteen years ago, David Letterman put CBS late night on the map and in the process became one of the defining icons of our network," said Leslie Moonves, president and CEO of CBS Corporation. "His presence on our air is an ongoing source of pride, and the creativity and imagination that the Late Show puts forth every night is an ongoing display of the highest quality entertainment. We are truly honored that one of the most revered and talented entertainers of our time will continue to call CBS 'home.'"[89]

According to a 2007 article in Forbes magazine, Letterman earned $40 million a year.[90] A 2009 article in The New York Times, however, said his salary was estimated at $32 million.[91] In June 2009, Letterman's Worldwide Pants and CBS reached an agreement to continue the Late Show until at least August 2012. The previous contract had been set to expire in 2010, and the two-year extension was shorter than the typical three-year contract period negotiated in the past.[91] Worldwide Pants agreed to lower its fee for the show, though it had remained a "solid moneymaker for CBS" under the previous contract.[91]

On the February 3, 2011 edition of the Late Show, during an interview with Howard Stern, Letterman said he would continue to do his talk show for "maybe two years, I think."[92] In April 2012, CBS announced it had extended its contract with Letterman through 2014.[93] His contract was subsequently extended to 2015.[94]

During the taping of his show on April 3, 2014, Letterman announced that he had informed CBS president Leslie Moonves that he would retire from hosting Late Show by May 20, 2015.[95] Later in his retirement Letterman occasionally stated, in jest,[96] that he had been fired.[97] It was announced soon after that comedian and political satirist Stephen Colbert would succeed Letterman.[98] Letterman's last episode aired on May 20, 2015, and opened with a presidential sendoff featuring four of the five living American presidents, George H. W. Bush, Bill Clinton, George W. Bush, and Barack Obama, each mimicking the late president Gerald Ford's statement "Our long national nightmare is over." It also featured cameos from The Simpsons and Wheel of Fortune (the latter with a puzzle saying "Good riddance to David Letterman"), a Top Ten List of "things I wish I could have said to David Letterman" performed by regular guests including Alec Baldwin, Barbara Walters, Steve Martin, Jerry Seinfeld, Jim Carrey, Chris Rock, Julia Louis-Dreyfus, Peyton Manning, Tina Fey, and Bill Murray, and closed with a montage of scenes from both his CBS and NBC series set to a live performance of "Everlong" by Foo Fighters.

The final episode of Late Show with David Letterman was watched by 13.76 million viewers in the United States with an audience share of 9.3/24, earning the show its highest ratings since following the 1994 Winter Olympics on February 25, 1994, and the show's highest demo numbers (4.1 in adults 25–54 and 3.1 in adults 18–49) since Oprah Winfrey's first Late Show appearance following the ending of her feud with Letterman on December 1, 2005. Bill Murray, who had been his first guest on Late Night, was his final guest on Late Show. In a rarity for a late-night show, it was also the highest-rated program on network television that night, beating out all prime-time shows.[99] In total, Letterman hosted 6,080 episodes of Late Night and Late Show,[1][4] surpassing friend and mentor Johnny Carson as the longest-serving late-night talk show host in U.S. television history.[2]

In 2018, Letterman began hosting a six-episode monthly series of hour-long programs on Netflix consisting of long-form interviews and field segments.[109] The show, My Next Guest Needs No Introduction with David Letterman, premiered January 12, 2018 with Barack Obama as its first guest.[110] The second season premiered on May 31, 2019.[111] Season 3 premiered on October 21, 2020, and includes Kim Kardashian West, Robert Downey Jr., Dave Chappelle and Lizzo as guests.[112] Season 4 premiered on May 20, 2022, with Billie Eilish as the first guest.[113]

In spite of Johnny Carson's clear intention to pass his title to Letterman, NBC selected Jay Leno to host The Tonight Show after Carson's departure.[114] Letterman maintained a close relationship with Carson through his break with NBC. Three years after he left for CBS, HBO produced a made-for-television movie called The Late Shift, based on a book by The New York Times reporter Bill Carter, chronicling the battle between Letterman and Leno for the Tonight Show hosting spot.

Carson later made a few cameo appearances as a guest on Letterman's show. Carson's final television appearance was on May 13, 1994, on a Late Show episode taped in Los Angeles, when he made a surprise appearance during a Top 10 list segment. In early 2005, it was revealed that Carson occasionally sent jokes to Letterman, who used them in his monologue; according to CBS senior vice president Peter Lassally (a onetime producer for both men), Carson got "a big kick out of it."[115] Letterman would do a characteristic Carson golf swing after delivering one of his jokes. In a tribute to Carson, all the opening monologue jokes during the first show after Carson's death were by Carson.

Lassally also claimed that Carson had always believed Letterman, not Leno, to be his "rightful successor".[116] During the early years of the Late Show's run, Letterman occasionally used some of Carson's trademark bits, including "Carnac the Magnificent" (with Paul Shaffer as Carnac), "Stump the Band", and the "Week in Review".

Oprah Winfrey appeared on Letterman's show when he was hosting NBC's Late Night on May 2, 1989. After that appearance, the two had a 16-year feud[117] that arose, as Winfrey explained to Letterman after it had been resolved, as a result of the acerbic tone of their 1989 interview, of which she said that it "felt so uncomfortable to me that I didn't want to have that experience again". The feud apparently ended on December 2, 2005, when Winfrey appeared on CBS's Late Show with David Letterman in an event Letterman jokingly called "the Super Bowl of Love".[118]

Winfrey and Letterman also appeared together in a Late Show promo aired during CBS's coverage of Super Bowl XLI in February 2007, with the two sitting next to each other on a couch watching the game. Since the game was played between the Indianapolis Colts and Chicago Bears, the Indianapolis-born Letterman wore a Peyton Manning jersey, while Winfrey, whose show was taped in Chicago, wore a Brian Urlacher jersey.[119] On September 10, 2007, Letterman made his first appearance on The Oprah Winfrey Show at Madison Square Garden in New York City.

Three years later, during CBS's coverage of Super Bowl XLIV between the Colts and the New Orleans Saints, the two appeared again in a Late Show promo, this time with Winfrey sitting on a couch between Letterman and Leno. Letterman wore the retired No. 70 jersey of Art Donovan, a member of the Colts' Hall of Fame and a regular Letterman guest. The appearance was Letterman's idea: Leno flew to New York City on an NBC corporate jet, sneaking into the Ed Sullivan Theater during the Late Show's February 4 taping wearing a disguise and meeting Winfrey and Letterman at a living room set created in the theater's balcony, where they taped their promo.[120]

Winfrey interviewed Letterman in January 2013 on Oprah's Next Chapter. They discussed their feud and Winfrey revealed that she had had a "terrible experience" while appearing on Letterman's show years earlier. Letterman could not recall the incident but apologized.[121]

Late Show went off air for eight weeks in 2007 during November and December because of the Writers Guild of America strike. Letterman's production company, Worldwide Pants, was the first company to make an individual agreement with the WGA,[122] allowing his show to come back on the air on January 2, 2008. In his first episode back, he surprised the audience with a newly grown beard, which signified solidarity with the strike.[123] His beard was shaved off during the show on January 7, 2008.

On June 8 and 9, 2009, Letterman told two sexually themed jokes about a daughter (never named) of Sarah Palin on his TV show. These included a statutory rape joke about Palin's then 14-year-old daughter, Willow, and MLB player Alex Rodriguez.[124] Palin was in New York City at the time with Willow, and none of her other children were at the game.[124] Some contemporaries questioned the racial connotations of joking about a Latino player of Dominican descent committing statutory rape.

In a statement posted on the Internet, Palin said, "I doubt [Letterman would] ever dare make such comments about anyone else's daughter" and that "laughter incited by sexually perverted comments made by a 62-year-old male celebrity aimed at a 14-year-old girl is disgusting."[125] On his June 10 show, Letterman responded to the controversy, saying the jokes were meant to be about Palin's 18-year-old daughter, Bristol, whose pregnancy as an unmarried teenager had caused some controversy during the United States presidential election of 2008. "These are not jokes made about [Palin's] 14-year-old daughter ... I would never, never make jokes about raping or having sex of any description with a 14-year-old girl."[125]

His remarks did not end public criticism. The National Organization for Women (NOW) released a statement supporting Palin, noting that Letterman had made "[only] something of an apology."[124] When the controversy failed to subside, Letterman addressed the issue again on his June 15 show, faulting himself for the error and apologizing "especially to the two daughters involved, Bristol and Willow, and also to the governor and her family and everybody else who was outraged by the joke."[126] Rodriguez demanded an apology for implying that he was a child molester. Letterman never specifically apologized to Rodriguez.[127]

On August 17, 2011, it was reported that an Islamist militant had posted a death threat against Letterman on a website frequented by Al-Qaeda supporters, calling on American Muslims to kill him for making a joke about the death of Ilyas Kashmiri, an Al-Qaeda leader who was killed in a June 2011 drone strike in Pakistan.[128] In his August 22 show, Letterman joked about the threat, saying "State Department authorities are looking into this. They're not taking this lightly. They're looking into it. They're questioning, they're interrogating, there's an electronic trail—but everybody knows it's Leno."[129]

On July 2, 1968, Letterman married his college sweetheart, Michelle Cook, in Muncie, Indiana; they divorced by October 1977.[151] He also had a long-term cohabiting relationship with the former head writer and producer on Late Night, Merrill Markoe, from 1978 to 1988. Markoe created several Late Night staples, such as "Stupid Pet/Human Tricks".[152] Time magazine wrote that theirs was the defining relationship of Letterman's career, with Markoe also acting as his writing partner. She "put the surrealism in Letterman's comedy."[153]

Letterman and Regina Lasko started dating in February 1986, while he was still living with Markoe. Lasko gave birth to their son, Harry Joseph Letterman, on November 3, 2003. Harry is named after Letterman's father.[154] In 2005, police discovered a plot to kidnap Letterman's son and demand a $5 million ransom. Kelly Frank, a house painter who had worked for Letterman, was charged in the conspiracy.[155]

Letterman and Lasko wed on March 19, 2009, in a quiet courthouse civil ceremony in Choteau, Montana, where he had purchased a ranch in 1999.[156][157][158] Letterman announced the marriage during the taping of his show of March 23, shortly after congratulating Bruce Willis on his marriage the week before. Letterman told the audience he nearly missed the ceremony because his truck became stuck in mud two miles from their house.[159] The family resides in North Salem, New York, on a 108-acre (44-hectare) estate.[160]

On October 1, 2009, Letterman announced on his show that he had been the victim of a blackmail attempt by a person threatening to reveal his sexual relationships with several of his female employees—a fact Letterman immediately thereafter confirmed.[161] He said that someone had left a package in his car with material he said he would write into a screenplay and a book if Letterman did not pay him $2 million. Letterman said that he contacted the Manhattan District Attorney's office and partook in a sting operation that involved the handover of a fake check to the extortionist.[162]

Joe Halderman, a producer of the CBS news magazine television series 48 Hours, was arrested around noon (EST) on October 1, 2009, after trying to deposit the check. He was indicted by a Manhattan grand jury following testimony from Letterman and pleaded not guilty to a charge of attempted grand larceny on October 2, 2009.[163] Halderman pleaded guilty in March 2010 and was sentenced to six months in prison, followed by probation and community service.[164]

A central figure in the case and one of the women with whom Letterman had had a sexual relationship was his longtime personal assistant Stephanie Birkitt, who often appeared on the show. She had also worked for 48 Hours.[165] Until a month before the revelations, she had shared a residence with Halderman,[166] who allegedly had copied her personal diary and used it, along with private emails, in the blackmail package.[167]

In the days following the initial announcement of the affairs and the arrest, several prominent women, including Kathie Lee Gifford, co-host of NBC's Today Show, and NBC news anchor Ann Curry, questioned whether Letterman's affairs with subordinates created an unfair working environment.[168] A spokesman for Worldwide Pants said that the company's sexual harassment policy did not prohibit sexual relationships between managers and employees.[169] According to business news reporter Eve Tahmincioglu, "CBS suppliers are supposed to follow the company's business conduct policies" and the CBS 2008 Business Conduct Statement states that "If a consenting romantic or sexual relationship between a supervisor and a direct or indirect subordinate should develop, CBS requires the supervisor to disclose this information to his or her Company's Human Resources Department".[170]

On October 3, 2009, a former CBS employee, Holly Hester, announced that she and Letterman had engaged in a yearlong secret affair in the early 1990s while she was his intern and a student at New York University.[171] On October 5, 2009, Letterman devoted a segment of his show to a public apology to his wife and staff.[172][173] Three days later, Worldwide Pants announced that Birkitt had been placed on a "paid leave of absence" from the Late Show.[174] On October 15, CBS News announced that the company's chief investigative correspondent, Armen Keteyian, had been assigned to conduct an "in-depth investigation" into Letterman.[175]

Beginning in May 1988, Letterman was stalked by Margaret Mary Ray, a woman with schizophrenia. She stole his Porsche, camped out on his tennis court, and repeatedly broke into his house. Her exploits drew national attention, with Letterman occasionally joking about her on his show, though he never named her. After she died by suicide at age 46 in October 1998, Letterman told The New York Times that he had great compassion for her.[176] A spokesperson for Letterman said: "This is a sad ending to a confused life."[177]

In 2005, another person was able to obtain a restraining order from a New Mexico judge, prohibiting Letterman from contacting her. She claimed he had sent her coded messages via his television program, causing her bankruptcy and emotional distress.[178][179] Law professor Eugene Volokh called the case "patently frivolous".[180]

Letterman is a car enthusiast and owns an extensive collection. In 2012, it was reported that the collection consisted of ten Ferraris, eight Porsches, four Austin-Healeys, two Honda motorcycles, a Chevy pickup, and one car each from automakers Mercedes-Benz, Jaguar, MG, Volvo, and Pontiac.[181]

In his 2013 appearance on Comedians in Cars Getting Coffee, part of Jerry Seinfeld's conversation with Letterman was filmed in Letterman's 1995 Volvo 960 station wagon, which is powered by a 380-horsepower racing engine. Paul Newman had the car built for Letterman.[182]

Letterman shares a close relationship with the rock and roll band Foo Fighters since its appearance on his first show upon his return from heart surgery. The band appeared many times on the Late Show, including a week-long stint in October 2014. While introducing the band's performance of "Miracle" on the show of October 17, 2014, Letterman told the story of how a souvenir video of himself and his four-year-old son learning to ski used the song as background music, unbeknownst to Letterman until he saw it. He stated: "This is the second song of theirs that will always have great, great meaning for me for the rest of my life". This was the first time the band had heard this story.[183][184] Worldwide Pants co-produced Dave Grohl's Sonic Highways TV series. "Letterman was the first person to get behind this project," Grohl said.[185]