Despite starring in arguably the best black TV sitcom and a number of successful comedy flicks, Will Smith has never done stand-up comedy before.

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In a recent episode of his new Facebook Watch series, Will Smith revealed that he turned to Dave Chapelle for advice in regards to his stand-up gig at the Peppermint Club in Los Angeles.

“The first thing I’ll tell you is confidence is key,” Chappelle told Smith. “The reason you should be confident is primarily because you’re Will Smith. I’ve been watching you for years — you’re actually a funny dude. I’ve spoken to you before, you’re a great conversationalist. What else do you really need to do?”


Dave then said it’s important to pick the “right sh*t to talk about” and went on to give the most important advice for any aspiring stand-up comedian.

“The best advice I ever got doing comedy was from a comedian that was not particularly good, but the advice was very important to me,” he said. “He said, ‘You are one of those comedians who think you have to be funny all the time. You don’t. But, you do have to be interesting all the time.’”

Chappelle assured that his show will be successful if he follows these tips.

“You can talk about anything, the more embarrassing, the more relatable you are. Because everyone thinks you’re perfect,” the comedian said. “Nobody’s perfect. But it’s fun to be self-aware in front of people. And a lot of times, they forgive themselves for something, just hearing somebody work through something.”