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: