Watch Will Smith Do Stand-Up Comedy, Get Advice From Dave Chappelle

Will Smith took to Facebook Watch for a new episode of Will Smith’s Bucket List, where the actor/comedian/rapper tackles several of the things he’s always dreamed of doing ranging from fear-inducing to fun. In the latest episode, he describes one of his most frightening challenges: performing stand-up for the first time as an opening act for Dave Chappelle. Smith met with the comedy veteran to get some pointers.

“I’ve never done stand-up,” Smith confesses in the clip. “Like, I’ve never used my life to create material to try to make people laugh.”

“Oh, OK, this is gonna be fun,” Chappelle says, before imparting a three-part checklist of advice.

“The first thing I’ll tell you is confidence is key,” Chappelle says. “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?” Chappelle adds. “All you need to do is pick the right shit to talk about. So then Number Two, pick the right shit to talk about.”

The third checklist item Chappelle says came from an unnamed comedian, whom he describes as not very good. However, Chappelle explains that it was the best advice he’s received. “He said, ‘You are one of those comedians who think you have to be funny all the time. You don’t. But, you have to be interesting all the time.'”

Smith employed Chappelle’s wisdom during his set, appearing confident while discussing his family life. “I kinda lost control of my house,” he says, before riffing on his son Jaden’s song, “Icon.” “He recorded it in my house, put it out and never said shit to me. I’m like, ‘Yo, Jaden, you think I could jump on that remix?'” His son apparently wasn’t that keen on that idea, so his dad said he “waited for him to go to sleep. I just got all my Grammys and just put them all over the house.”

In another clip, he pokes fun at himself and his “business” being aired via his wife Jada Pinkett Smith’s show. “Jada giving it up on Red Table Talk, boy,” he says, before acknowledging that her being in the audience was a surprise and makes it harder to joke about. “Sorry, babe… I wasn’t expecting Jada to be here. I wasn’t expecting to say it in front of you,” he confesses, before someone tells him he should stick to the script, which causes him and the audience to erupt in laughter.

New episodes of Will Smith’s Bucket List air on Wednesdays via Facebook Watch.