Dave Chappelle Helps a Promising New Stand-up Named Will Smith

Will Smith is many things — an actor, a rapper, a genie, and a father to very famous and talented children — but one thing he never was, until now, is a stand-up comedian. In the new episode of his Facebook Watch series Will Smith’s Bucket List, Smith decides to give the tough gig of live comedy a shot because, as he says, “Stand-up is on my bucket list because I’ve always been terrified of it.” Neal Brennan, Rell Battle, Q-Tip, Alfonso Ribeiro, and Michael Che all make appearances throughout the episode, in which Smith turns to stand-up master Dave Chappelle for some tips and advice on what goes into creating a solid stand-up set. (Some of Chappelle’s advice includes “Be interesting all the time,” “Fear is good for comedy,” and “Comics are assholes.”) The episode culminates when Chappelle introduces Smith at the Peppermint Club in West Hollywood, where he faces his live-comedy fears in front of a surprised audience as well as a smiling Jada Pinkett Smith seated at a nearby booth. So what lessons did Smith learn from his brief time as a stand-up? “If you are comfortable, you’re not growing … It’s what Buddha called ‘sublime detachment’ — life is so much fun when you don’t give a fuck.”

Dave Chappelle Teaches Will Smith How to Do Stand-up