Dave Chappelle Teaches Will Smith How To Do Standup Comedy (Video)

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Hip-Hop Fans, we need your help...We recently launched AFH TV, a streaming video service focused on Hip-Hop culture. We already have exclusive interviews, documentaries, and rare freestyles featuring some of Rap’s most iconic artists and personalities. But, there is so much more to come--movies, TV series, talk shows--and we need your support to make it a reality. Please subscribe to AFH TV. It is only $1.99/month or $12/year, and offers 30-day free trials. Thank you.

Will Smith is many things. Actor, MC, humanitarian, father, social media influencer and husband are some of the titles he holds. However, the West Philadelphia, Pennsylvania native says that standup comedy is a fascination of his that gives him fear. Smith’s role on The Fresh Prince Of Bel-Air, in film, and on some of his music with DJ Jazzy Jeff & The Fresh Prince has been presented with comedy. However, in a new video, Smith reveals that much of his act is an overcompensation for a personal shyness. The gregarious and romantically charming personalities that Will plays are not a natural extension of the 50-year-old media mogul.

“The crazy thing is that I’m more nervous about doing standup than I am bungee-jumping out of a helicopter over the Grand Canyon,” Smith begins in the latest episode of Will Smith’s Bucket List. He says that unlike performing music on stage, if he slips in his vocal delivery, the audience will not bail him out. Will proclaims, “To be able to stand on a stage with a microphone [and nothing else but a crowd] to me, is the hardest thing in entertainment.”

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In preparing an act as part of a year-long 50th birthday celebration, Will Smith links with the man he considers “the master” of standup: Dave Chappelle. While providing some tricks of the trade, Dave has allowed The Fresh Prince to open for him, seven days after the two discussed the art of standup. At a Las Vegas hotel, Dave gives Will a checklist of what he feels are the three jewels of the standup trade:

1. Confidence Is Key

Chappelle suggests that Will Smith, more than nearly anybody on the planet, has a right to be confident. He adds that he finds him funny and “a great conversationalist,” so this should come naturally.

2. Pick The Right Sh*t To Talk About

3. Be Interesting All The Time

Dave says, “The best advice I ever got doin’ comedy was from a comedian that was not particularly that good. The advice was very important to me. He said, ‘You are 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.”

Weaving the principles together, Dave suggests, “Look at it like you’re having a conversation with no rebuttal. They’re talking back with their laughter, or in many cases—my case—their disapproval.” He continues, “But especially someone of your stature, if they can feel you, they’ll never forget you.” Dave adds that embarrassing revelations make standup comedians, especially celebrities, more relatable to the audience. He says that in addition to common ground, the humility helps members of the audience forgive themselves for the same things that the comedian admits to doing or feeling.

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Preparing for his debut, Will Smith admits, “I think I’ve earned the right for gigantic public failure.” The Hollywood superstar’s career has been one marked by victory, not defeat. However, later in the nearly half-hour video, Smith reveals that he has guards, including the need for approval and the fear of people supporting him based on his celebrity.

At lunch, Dave’s Chappelle’s Show partner, Neal Brennan, suggests Will share with the audience his bucket list reason for doing standup. The producer and co-writer of the show has several Netflix specials, like Dave. Q-Tip calls Dave and soon joins the affair.

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After returning to California, Will takes lessons from other comedians. Rell Battle suggests that Smith pull material from his family, all of whom are public figures, to break some new terrain.

Will’s Fresh Prince co-star, Alfonso Ribeiro, also joins his friend to prep. “Every time I confront a fear, I feel more free,” Smith says, after explaining how his TV character helped him unlock courage and courtship with women during his maturity.

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Ahead of the big night, Dave Chappelle tells Will Smith, “fear is good for comedy” as the two have drinks at Chateau Marmont before the show. “You’re a big star. If you look anybody directly in the eyes, they might look away. That’s the power of celebrity. And you’re a good dude; you don’t put on any airs, you’re just like f*ck it. Being a good dude in comedy, that’s rare; comics are assholes.” Moments later, Dave admits that when Eddie Murphy attends his shows, he gets nervous. He feels as though Murphy is better than him at the art.

The video concludes with Smith’s standup appearance at The Peppermint Club in L.A. near the 15:00 mark. Jada Pinkett-Smith, Willow Smith, and other members of the family are in the audience. In his act, he references hopping onto Jaden Smith’s “Icon (Remix)” without his son’s permission, and schooling the rapper on who in the family did it first.

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In the closing sequence, Will is seen freestyling besides Dave, with John Mayer on guitar. This week, Chappelle was in the news for joking remarks he made on Mayer’s live video, aimed at fellow guest, singer Daniel Caesar.