Kevin Brennan

Brennan played himself in an episode of Pete Holmes' HBO series Crashing that aired in 2019. A roast of Kevin Brennan was held at The Stand comedy club in New York City that same year. Roasters at the event included comedians Dan Soder, Jim Norton (in character as Chip Chipperson), Krystyna Hutchinson and Corinne Fischer of the Guys We Fucked podcast, Patty Rosborough, Chad Zumock and Mike Bocchetti.

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." 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.

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 laugh at your jokes and not like you."

Brennan and fellow New York-based comedian Lenny Marcus started the podcast titled Misery Loves Company in January of 2016. Marcus quit the podcast after ten months following several on-air and off-air disagreements between the two comedians. Brennan continued the podcast with various co-hosts. then went on to host it along with the show's producer, Adam Hiniker. Anthony Cumia became a fan of Brennan's tirades against other comedians on Misery Loves Company and brought Brennan to his Compound Media network in 2017, where Brennan hosted his second podcast, Burning Bridges, until 2019. From 2016 to 2017 Brennan was also a repeat panelist on Red Eye w/ Tom Shillue.

Brennan was voted "Best Comedian" at the 2005 Aspen Comedy Festival and his half-hour stand-up special was featured on the HBO that same year. He was a 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.

From 2003 to 2005 Brennan made multiple appearances on Last Call with Carson Daly. Brennan was voted “Best Comedian” at the 2005 Aspen Comedy Festival, which lead to his half-hour stand-up special on the HBO series One Night Stand that same year. He was one of six comedians featured on the 2007 cross-Canada Just for Laughs comedy tour, which also featured Greg Behrendt, John Wing, Louis Ramey, Fiona O'Loughlin and Tom Papa. He also performed at the Just For Laughs festival in Montreal in 2009. In 2011 Brennan wrote for the Comedy Central series Sports Show with Norm Macdonald.

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 25 season while Colin Quinn held the anchor post. 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 and Brennan decided not to return as a writer for the following season.

In 1997 Brennan appeared in a small role in the film Half Baked which was co-written by Chappelle and Kevin's brother Neal Brennan. By this time Brennan was well established in the New York comedy circuit and had appeared twice on Late Show with David Letterman. 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.

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.

In 1993 Brennan appeared on the entertainment competition show Star Search where he competed against, and was beaten by, a 19 year old Dave Chappelle.

Within two years of moving to New York City, Brennan was hosting open mics and other comedy shows at the Boston Comedy Club (a now defunct comedy club in New York City.) By the early 1990s he was appearing on A&E's stand-up comedy series An Evening at the Improv and Caroline's Comedy Hour.

Brennan first started stand-up in Chicago in the 1980s at the suggestion of a coworker at a restaurant where he was working. He moved to New York City in 1987 to further pursue a career in stand up comedy.

Kevin Brennan (born May 2, 1960) is an American stand-up comedian and writer. He is best known for his work on Saturday Night Live's Weekend Update in 1999 and 2000.