Dennis and Callahan

[3] The duo were scheduled to return to the air together that day for the first time in over three months after Callahan's long medical absence, and after a one-week vacation by Dennis.

[4] On August 16, 2007, the Boston Globe reported that Dennis and Callahan were in negotiations to move their show to WCRB-FM, a Boston-based radio station that was considering changing its format from classical music to all sports.

Part of the deal includes Entercom obtaining a 50 percent stake in WCRB-FM with the intent to keep the station on a classical format, thus preventing a move there by Dennis and Callahan.

[6] The show continued to air daily as the Dennis and Callahan Show with rotating guest hosts including Steve DeOssie, Dan Patrick, Bob Lobel, Jon Meterparel, Bob Halloran, Ron Borges, Greg Dickerson, John Rooke, Steve Burton, Butch Stearns, Craig Mustard, Ted Johnson and Larry Johnson.

According to newspaper articles, the exchange allegedly was:[16] METCO is a state program that buses inner-city Boston students to nearby suburban schools.

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.

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".

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.

[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).

[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.)

[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.

[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.