This Video of Dave Chappelle Teaching Will Smith Stand-Up Is Extremely Will Smith

Naturally, Smith got really, really into it.

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Mar 13 2019, 10:15pm

Screengrab via Facebook

For some reason, Will Smith lives to conquer his extravagant list of fears and share them with us for #content. On his Facebook show Will Smith’s Bucket List, he’s bungee jumped out of a helicopter over the Grand Canyon, gone scuba diving with sharks, and now, for Wednesday’s episode, we’ve apparently gotten to his lifelong fear of absolutely bombing at stand-up comedy. While all Smith exploits are extra as fuck, this one was really up there: In typical Smith fashion, he starts by calling up his buddy Dave Chappelle, who casually throws him into the deep end and invites Smith to open for him—giving him seven days to put together a set for the first time.

Their prep sessions for the task ahead of him are just as casual. Over a handful of fancy meals, Chappelle's main pillars of advice are to stay confident, “pick the right shit to talk about,” and keep his stories as embarrassing as possible. Chappelle also passed along another nugget he picked up from a fellow comedian, who told him, “You’re one of these comedians that thinks you have to be funny all the time, and you don’t. But you do have to be interesting all the time.” One mock performance in a confusingly empty mansion room later, and Smith is just about ready: After a little heart-to-heart with Chappelle on the way to the show, he goes for it.

And his set isn't half bad! He apparently took that advice about ragging on himself to heart, spending most of his time onstage riffing on how no one in his family ever tells him what the hell they're up to. Case in point: He had no idea that Jaden Smith's "Icon" was going to drop until he saw it on Spotify, and when he asked for a verse, his son turned him down.

“While he was still sleep, I just got all of my Grammys and put them all over the house,” Smith said.

By the end, Smith was getting props from Michael Che and Michelle Wolf backstage and somehow closing the show by spontaneously rapping like a dude from The Sugarhill Gang, which came out of nowhere. Evidently, he felt pretty good about crossing the whole stand-up thing off his bucket list.

“Every time I confront a fear, I feel more free,” he said, in classic "I am extremely wholesome" Will Smith form. “It’s what Buddha called sublime detachment. Life is so much fun when you don’t give a fuck!”

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