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."

For his third and final tips, Chappelle recalls advice from a comedian that he admits was "not particulary good" but gave him the best advice he's received. 

"He said, 'you are one of these comedians that think they have to be funny all the time and you don't. But you do have to be interesting all the time,'" Chappelle recalled. "And it works... you have to look at it like you're conducting a conversation with no rebuttal. They're talking back with their laughter—or in my case—their disapproval. But—especially someone of your stature—if they feel you, they'll never forget you." 

Smith used this advice and took on comedy for the first time, winning over the crowd in his stand-up debut.