Diddy’s Most Hilarious Moments – XXL
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Diddy wears many titles proudly: artist, businessman, entrepreneur, music executive, deal-closer, mover and shaker, father, son and all-around boss. However, another descriptor that can be added to the list is comedian. And while Puff, who turns 52 years old today (Nov. 4), isn’t known to tell jokes on a microphone and in front of an audience, he’s provided many people with organic laughter via his dance moves, mantras, life-related anecdotes and much more.
If you ask those who have been around Diddy for years, they likely can recount endless hilarious moments they’ve shared with the Bad Boy Records CEO. And thanks to the advancement of social media, fans of the Mount Vernon, N.Y. native have had a front-row seat to the sometimes intentional—but presumably not—stomach-clenching moments.
Over the summer, Brother Love recollected a time from his childhood when he woke up with 15 roaches on his face. The self-made millionaire said that defining moment inspired him to never settle or let go of his dreams. Now, Diddy had several non-believers voice their opinions about the story online, so whether or not it’s true, only he knows. However, as Puff retold the account on his Instagram page, he was devouring a mango. He then capped off the tale by putting on his swimming googles and jumped into his infinity pool.
He even offered more context during a conversation with Vanity Fair called 4 Minutes of Sean “Diddy” Combs Being Sean “Diddy” Combs.
Diddy has a penchant for spreading positivity and love, hence him changing his middle name to Love last year. But there’s also a humorous and playful layer to Puff that shouldn’t go unnoticed. In fact, it should be celebrated.
So, for Diddy’s 52nd birthday, XXL highlights some of his funniest moments below.
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Hilarious Staredown With Artist on Fox’s The Four
During season two, episode four of the singing competition show The Four in 2018, Diddy had a staredown with contestant Elijah Connor after telling Connor his performance wasn’t all that great. The hilarious moment went viral and has been used as memes for years.
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“Savage” Moment From Can’t Stop Won’t Stop Documentary
In 2017, Diddy released the Can’t Stop Won’t Stop documentary, which focused on the preparation for the 2016 Bad Boy Reunion tour. He passionately affirmed that what he wants, he has to get.
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Has a Fear of Clowns on The Ellen DeGeneres Show
In 2018, Diddy appeared on The Ellen DeGeneres Show and Ellen proved that the rapper-entrepreneur is indeed afraid of clowns.
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Overcomes Fear of Clowns by Dancing in Pennywise Costume
However, for Halloween in 2018, Diddy debunked the claims of his fear of clowns by dressing as Pennywise from the horror film It.
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Chris Brown Teaches Diddy How to Do the Woo Walk
While Diddy had an event at his home back in January, he received lessons from Chris Brown on how to do the Woo Walk.
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Busts Out Dance Moves at His 50th Birthday Party
In typical Puff fashion, he hit the dance floor on his 50th birthday in 2019 with some shoulder-heavy moves.
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Makes Da Band Members Walk to Get Cheesecake From Junior’s in Brooklyn
In 2002, Diddy made Da Band—the famed hip-hop group from the reality competition show Making the Band—walk from Times Square in New York City to downtown Brooklyn to get him a slice of cheesecake from the famous Junior’s restaurant.
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Shows Off Diving Skills in the Pool
Diddy may not be a Michael Phelps-level diver, but last November, he flexed his skills in his pool at home like he is one.
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Prepares His New Year’s Eve 2020 ’Fit
In preparation of New Year’s Eve last year, Diddy prepped his ’fit by choosing from a selection of his iced-out jewels, which he planned to wear for the evening as he ushered in 2021.
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Gives Speech on Paying People So He Doesn’t Have to Work
In 2019, Diddy put people on game to see how he manages to be as successful as he is: he pays people so he doesn’t have to work as hard.
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