Dennis and Callahan

• Patriots quarterback Tom Brady every Monday during football season.
• ESPN's Tim Hasselbeck appears every Monday during football season.

• Red Sox pitcher Curt Schilling appeared every Tuesday during baseball season. Schilling donated his appearance fee to the ALS Association. He currently is a regular guest on The Big Show.
• an Ex-Con named Rabbit often calls about Aaron Hernandez and other criminals
• Former Boston College Eagles football coach Jeff Jagodzinski appeared frequently during the college football season on a segment they called the Coach Jags Show.
• Patriots quarterback Matt Cassel appeared every Monday during the 2008 football season.
• David "El Presidente" Portnoy, publisher of Barstool Sports, appeared on the show each Friday during the summer of 2011. The station dropped his appearances on August 12 after Barstool published a nude photograph of Patriot quarterback Tom Brady's two-year-old son with accompanying commentary on the size of the child's genitalia.[10][11][12] However, he was welcomed back to the show as a guest in May 2015 to discuss Brady in the wake of his Deflategate suspension and the "Free Brady" rally at Gilette Stadium (though there is no word on whether he will return as a regular guest.)
• Celtics head coach Doc Rivers every Thursday during basketball season.

In 1999, the Boston Globe's executive sports editor, Don Skwar banned its sportswriters from the Globe from appearing on the Dennis & Callahan morning show because of its perceived lowbrow humor. This came two weeks after he banned Globe sportswriters from appearing on WEEI's afternoon The Big Show after columnist Ron Borges appeared on the show and used a racial slur to describe New York Yankees pitcher Hideki Irabu. After the ban, WEEI retaliated by banning Globe sportswriters from all WEEI programs.[13] It was also about this time that Michael Holley, who was involved with both, chose his side and departed from the Globe to join WEEI full time. However, the show has welcomed Globe stalwart Bob Ryan as a guest host and did welcome former Globe columnist Jackie MacMullan while Ryan and Kathryn Tappen were guest hosting in order to share a story about Whitey Bulger soon after he was caught in the summer of 2011.[14]

On September 29, 2003, during a segment called 'headlines', where they read and comment about current news stories, Callahan and his morning co-host John Dennis made racist comments while discussing a story about an escaped gorilla.[15] The gorilla had escaped from the Franklin Park Zoo and had been recaptured at a bus stop. According to newspaper articles, the exchange allegedly was:[16]

Callahan: "They caught him at a bus stop, right -- he was like waiting to catch a bus out of town."

Dennis: "Yeah, yeah -- he's a METCO gorilla."

Callahan: "Heading out to Lexington."

Dennis: "Exactly."

METCO is a state program that buses inner-city Boston students to nearby suburban schools. The racist comments compared poor, mostly African-American children to gorillas. WEEI general manager Tom Baker suspended both hosts for two days, then extended the suspension to two weeks after the Blue Cross-Blue Shield (Blue Cross Blue Shield of Massachusetts) pulled $27,000 in ads and in turn donated that money to METCO. Dunkin' Donuts responded by ceasing all advertising that involved the voices of John Dennis or Gerry Callahan.[17] Both hosts apologized and were sent to sensitivity training. WEEI also agreed to provide free advertising for the METCO program on the radio station. In November 2003, WEEI General Manager Tom Baker was replaced by Julie Kahn. Station executives denied there was a connection between the METCO incident and Baker's replacement.[18]

On June 2, 2005 Callahan, who has been accused of making homophobic comments on the air, upset some listeners during interviews with Red Sox CEO Larry Lucchino and relief pitcher Mike Timlin discussing the upcoming visit of Carson Kressley and the cast from Queer Eye at Fenway Park. Kressley and his co-hosts were scheduled to throw out the first pitch at Fenway Park on Sunday, June 5, 2005 before the Red Sox faced the Los Angeles Angels. In questioning Lucchino, Callahan asked if the team had received any complaints about "'fruitcakes sashaying' in front of children and families, and on a Sunday, of all days". In a later interview, Mike Timlin voiced his opinion that "homosexuals are not living correctly". Approached later by reporters from the Boston Globe, station manager Jason Wolfe claimed that Callahan did not object to Kressley being gay, but rather that "it's the openness and the flaunting of it".[19][20]

In September 2005, a profanity-laced audio file was posted on Barstool Sports, containing a voice mail message from John Dennis threatening rival sports radio personality Ryen Russillo (then of 1510 The Zone, later the co-host of SVP & Russillo on ESPN Radio with Scott Van Pelt and then of Russillo and Kannell on ESPN Radio with Danny Kannell) [21] In the audio tape, Dennis accuses Russillo of being a drunk and hitting on his daughter. After the incident, the New England Patriots had Russillo removed from WBCN's post-game show with Gary Tanguay & Company. At the time WBCN, which was owned by CBS, held broadcast rights to Patriot games. Dennis denied any responsibility for the Patriots' decision.

In March 2006, some listeners of the Dennis and Callahan Show were upset when they conducted an in studio interview with Kevin Weeks, a former member of Whitey Bulger's South Boston based criminal organization. Weeks had admitted to committing armed and unarmed assaults, kidnappings and being an accessory to several murders on behalf of Whitey Bulger and had played a role helping Bulger escape arrest.[22] His appearance on the show was to promote his book, Brutal : The Untold Story of My Life Inside Whitey Bulger's Irish Mob (ISBN 0-06-112269-6). Some listeners felt that it was wrong for the show to help Weeks promote his book. Callahan told the Boston Herald that they wrestled with whether to "put this thug on air." but the bottom line, he said, "It's good radio."[23]

In June 2007, Dennis apologized on-air to the Doyle family of Massachusetts to avert a potential lawsuit for defaming the family on the radio. The controversy began in February 2007, when Doyle family member Patrick Doyle was sentenced to five years probation after pleading guilty to child endangerment.[24][25] Doyle was present when a 9-year-old girl was repeatedly raped by two other men in the bed next to him while he had sex with two women, one of whom is the girl's mother. Doyle comes from a family that includes a serving District Court Judge, a retired District Court Judge and an Essex County Assistant District Attorney. While discussing the sentence which they believed was far too lenient, Dennis and Callahan accused members of the Doyle family of interceding on behalf of Doyle and suggested that "the fix was in".[26]

On an April 1 show in 2008, both Dennis and Callahan during a top ten April fools prank list made mention to a prank done by the radio show duo Opie and Anthony in 1998. At the time, the duo was hosting the afternoon drive show on WAAF-FM and had the highest ratings in the market. Said prank involved hosts Gregg “Opie” Hughes and Anthony Cumia insinuating that then-Boston mayor Thomas Menino had been killed, but eventually got so far out of hand that it led to their firing a week later after Menino filed a complaint with the Federal Communications Commission.

During the segment where they revisited the incident, Dennis openly wondered what had happened to “those guys”, to which Callahan responded by saying that they were “working at McDonald’s with a pedophile.” The comment did not sit well with Hughes and Cumia, who were airing at the time on WBCN-FM in the same time slot that Dennis and Callahan were, and they played the clip on air. This led to various Opie and Anthony fans bombarding WEEI with calls regarding where Opie and Anthony were working (among other prank calls) and forced the station to temporarily reduce the amount of calls being taken from listeners.[27] (Opie and Anthony was eventually dropped by WBCN by the end of the year due to a continued decline in ratings, which led to the cancellation of the program by CBS Radio shortly thereafter.)

In November 2008, the duo drew criticism from the office of Massachusetts Secretary of State William Galvin after they told listeners that the election had been postponed and that Democrats should cast their votes on November 5 (the day after Election Day). Galvin's spokesperson said the show was doing a disservice to voters and warned them that they could be violating a state law against interfering with elections. In response, Gerry Callahan stated "Obviously it was a joke and I think most listeners understood it was a joke".[28]

In January 2009, a man from Cambridge, Massachusetts, was charged in relation to a series of obscene and threatening phone calls made to the station over a period of two months. The man, who was apparently upset with the on-air duo's support of Senator John McCain's presidential candidacy, allegedly called the station starting in October 2008 threatening the show's hosts as well as WEEI program director Jason Wolfe and vice president of Entercom New England Julie Kahn. The man who was charged with two counts of criminal harassment, two counts of threats to commit a crime and a single count of making annoying phone calls.[29][30] In a plea bargain in February 2009, the man pleaded guilty to one of the charges against him and was sentenced to probation for a year. He must also undergo anger management counseling, perform 20 hours of community service and stay away from the victims and never call the station again.[31]

In April 2015, Dennis wrote in the Boston Herald that he was taking an indefinite leave of absence from WEEI in order to enter rehab and address his alcoholism. Callahan and Minihane stated their support on the air, and after a successful stay of roughly a month, Dennis returned to the show sober.