will smith stand up dave chappelle
Will Smith's Bucket List / Facebook Watch

Now that he’s 50, Will Smith is doing everything he’s been too scared to do in his new show Will Smith’s Bucket List. The latest adventure undertaken by the actor and rapper was performing a stand-up comedy set.

Considering Smith is an accomplished actor and rapper, it’s somewhat surprising he’s never tried his hand at stand-up before. However, he explained that since stand-up is just “you, a microphone, and a crowd,” he finds it daunting. He said, “Stand-up is on my bucket list because I’ve always been terrified of it… I’m more nervous about stand-up than I am about bungee jumping out of a helicopter over the Grand Canyon.”

To help him cross stand-up off his bucket list, Smith enlisted the help of stand-up superstar Dave Chappelle. Chappelle agreed to let Smith open for him – with just a week to prepare. However, Chappelle did give the actor some pointers and tips: “1. Confidence is key. You should be confident because you’re Will Smith… 2. Pick the right shit to talk about… 3. Be interesting all the time.” Easy, right?

Taking this on board, Smith managed to do a decent job, getting the audience laughing with a set about how he’s dealing with his family members (who were in the audience) being successful in their own right. One of the funniest moments is when he’s talking about his son Jaden’s music. Smith said he asked if he could be on a remix Jaden’s song “Icon,” but Jaden “just looked at me like I’m the second-best rapper in my house.”

Watch the full episode below. The set starts at around 16 minutes in.

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