Brennan and Dave Chappelle met when both were aspiring stand-ups. Through his older brother, an established stand up comedian and comedy writer Kevin Brennan, Brennan got a part-time job working as the doorman at Boston Comedy Club in New York City where Chappelle was a frequent performer. They became good friends and collaborated on jokes. They co-wrote the film Half-Baked which starred Chappelle. In an interview on Inside the Actor's Studio, Chappelle admitted that he and Brennan could not help but see each other as a painful reminder of the box-office failure of Half-Baked and lost touch with each other. Four years later, they rekindled their partnership to create the sketch comedyshow, Chappelle's Show, which premiered in January 2003. The duo wrote the sketches themselves with very little outside help.
Brennan is frequently mentioned during Chappelle's stand-up routines.
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