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Dave Chappelle and Will Smith

Source: Sadao Turner / Sadao Turner

Since celebrating his 50th birthday by channeling his inner-Trevor and bungee jumping over the Grand Canyon, Will Smith has embarked on a quest to live out all of his crazy dreams. This goal led Smith to seek out comedy guru Dave Chappelle in hopes that his advice would help deliver a perfect stand-up routine.

In this episode of Facebook Watch’s Will Smith’s Bucket List, the rapper-turned-actor confesses to Chappelle that despite assuming comedic roles, he’s never tried to perform a stand-up set.

“I just wanted to sit with you and get some pointers and ideas,” Will said at the video’s 12-second mark. “I’ve done stand-up. Like, I’ve never used my life to create material to make people laugh.”

This opportunity to teach his craft to a friend excited Chappelle, who then urged post-production to utilize the “lower-third” as he ran through comedy tips.

“I’ll run down a checklist, alright? And I don’t know who’s the director but you might want to put these thing on the lower-third,” Chappelle jokes before starting the lesson.

“The first thing I’ll tell you is confidence is key. The reason you should be confident is primarily because you’re Will Smith,” Chappelle said bluntly. “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?,” he continued. “All you need to do is pick the right shit to talk about. So then number two, pick the right shit to talk about.”

And if Will needs more pointers, he can always rely on D.L. Hughley:



Article Courtesy of Complex and 93.1 WZAK-FM Cleveland

First and Second Picture Courtesy of Sadao Turner

First Video Courtesy of Rolling Stone and Complex

Second Video Courtesy of Facebook

Third Video Courtesy of Warner Bros. Television and YouTube

Will Smith Attempts to Do Stand-Up Comedy with Help From Dave Chappelle  was originally published on