Brennan was voted "Best Comedian" at the 2005 Aspen Comedy Festival and his half-hour stand-up special was featured on HBO that same year. He was featured on the 2007 cross-Canada Just for Laughs comedy tour and performed at the Just for Laughs festival in Montreal in 2009. He was also a repeat panelist on Red Eye w/ Tom Shillue in 2016 and 2017.
Brennan first started stand-up in Chicago in the 1980s at the suggestion of a coworker at a restaurant where he was working.[6][7] He moved to New York City in 1987 to further pursue a career in stand up comedy.[5][7]
In 1993, Brennan appeared on the entertainment competition show Star Search where he competed unsuccessfully against 19-year-old Dave Chappelle.[13]
Brennan first appeared as a guest on Late Night with Conan O'Brien in 1994 and went on to make multiple appearances on the show from 1995 to 2007.[14]
In 1997, Brennan appeared in a small role in the film Half Baked, which was co-written by his brother Neal Brennan and Chappelle.[15][16] By this time Brennan was established in the New York comedy circuit and had appeared twice on Late Show with David Letterman.[17] That same year the Brennan brothers had a development deal with NBC and Universal for a sitcom based on their own experiences growing up in an Irish-Catholic family with 10 kids in Philadelphia.[17]
Saturday Night Live (1999–2000)
Brennan was a writer for Saturday Night Live in 1999 and 2000 and also appeared on the show as a Weekend Update correspondent in two episodes of the show's 25th season while Colin Quinn held the anchor post.[3][18][19] Quinn left Saturday Night Live in 2000 and Brennan was in contention for the anchor position but, after the job was given to Jimmy Fallon and Tina Fey, Brennan decided not to return as a writer for the following season.[20]
Brennan started the comedic podcast titled Misery Loves Company(MLC) in January 2016, and added fellow New York-based comedian Lenny Marcus as his co-host. Marcus quit the podcast after ten months following several on-air and off-air disagreements between the two comedians.[3]
In 2018 he produced a live comedy show in New York City called White Guys Matter that was billed as "all white guys" and "no safe spaces" with the promise to "make comedy great again."[27][28] Comedian Aaron Berg, who performed at the New York show, brought the show to Yuk Yuk's comedy club in Toronto, Canada that same year, causing several local comedians to take to social media to protest the show.[28][29]
In October 2022, Brennan, along with fellow comedian Bob Levy, opened a comedy club called the Brennan & Levy's Comedy Loft in Vineland, New Jersey.[33][34]
Comedic style
Brennan's delivery has been described as "laid-back" and "laconic".[4] He is also known for insult comedy directed at members of the audience, and for jokes about racism, pedophilia and misogyny.[7] As his podcast title Burning Bridges suggests, Brennan is also known for confrontational statements about other comedians and podcasters.[3] Brennan drew public criticism for his remarks about the unexpected death of Friends actor Matthew Perry on social media, in late October 2023.[35]
In a 2017 interview with New York magazine, comedian Jim Gaffigan was quoted as saying: "I am a New York comedian in the vein of like Dave Attell and Kevin Brennan, where they're supposed to laugh at your jokes and not like you."[36]
^"City Lights Guide: Comedy/Magic". Daily News. New York City, New York, United States. May 28, 1989. p. 19. Retrieved April 20, 2020 – via Newspapers.com. BOSTON COMEDY CLUB (82 West Third St., 477-0622):Kevin Brennan hosts "Comedy Showcase" tonight at 9...
^"City Lights Guide: Comedy/Magic". Daily News. New York City, New York, United States. June 11, 1989. p. 19. Retrieved April 20, 2020 – via Newspapers.com. BOSTON COMEDY CLUB (82 West Third St., 477-0622):Kevin Brennan hosts "Comedy Showcase" tonight at 9...
^"City Lights Guide: Comedy/Magic". Daily News. New York City, New York, United States. September 3, 1989. p. 19. Retrieved April 20, 2020 – via Newspapers.com. BOSTON COMEDY CLUB (82 W. 3RD ST., 477-0622): Jimmy Tingle performs in his one-man show tonight. Kevin Brennan hosts "Open Mike" Mon...