Diddy's Top 20 Most Disturbing Videos of All Time: From Smacking Jay-Z's Butt to Flirty Moments With Celebrities

Diddy is a name that is somewhat synonymous with entertainment scandal and intrigue. He has a mean, larger-than-life persona, so it makes sense that those moments always seem to happen to him in some way, some weird and headline-making moments.

His behavior regularly straddles the thin line between humor, platonic intimacy, and decorum — from party craziness to profoundly personal.

That mishmash of events serves to illustrate the madness that follows him everywhere, as well as the strangeness of his stardom and other aspects of his life.

These events, both fascinating and alarming, reveal the unpredictability of Diddy's life.

Auction Night

Diddy auctions off a date night with himself, cracking questionable jokes about what the winning bidder can get.

DJ Incident in London

The DJ faints at a Diddy party, a scene we all expect to see to be dystopian and insane.

Closeness with Biggie

Footage raises questions about the nature of Diddy's relationship with Biggie.

TikTok Humiliation

After a previous fight with his ex-girlfriend Cassie Ventura, Diddy shares TikTok, which leads to public humiliation.

Self-Destructing Invites

Jimmy Fallon dished that Diddy's party invites self-destructed, which speaks to the secretive and exclusive nature of the shindigs.

Hotel Attack Footage

Newly released footage showing Diddy chasing and assaulting Cassie in a hotel, leading to serious allegations against him.

Strip Club Fun with Mom

Diddy posts a video of him and his mother getting to the borderline of propriety at a strip club.

Crossdressing Clip

Diddy shares a crossdressing clip on Snapchat, revealing his bizarre and narcissistic sense of humor.

Kiss with Birdman

Like a small child whose social boundaries have been thrown out the window, Diddy was on the hunt for an awkward kiss with Birdman during an interview.

Insult to Injury

At the Golden Globes, Diddy attempts to kiss Bono on stage but is met with rejection, creating an awkward moment.

Get Sexy

Diddy reveals his extensive hotel room mood-setting process to Conan O'Brien.

When Diddy Gets Flirty With Meek Mill

Diddy's awkwardly flirty comments on Meek Mill result in an uncomfortable exchange.

Diddy With Shirtless Men

Diddy shares a video of himself on a balcony with shirtless men, leading to strange and uncomfortable behavior.

Smacking Jay-Z

Diddy smacked Jay-Z's butt during an entire ass-ridden event — a blurred line between friendship and business.

Diddy Keeping Women Around

Diddy expresses his need to keep women close by locking them in a room. We get a real glimpse into his controlling behavior with this one.

Surprising Mike Tyson

Diddy surprises Mike Tyson on a live TV appearance.

Russell Brand Date Night

Diddy filmed a date-like private jet outing with Russell Brand, creating a totally awkward vibe.

48 Hours with Justin Bieber

Diddy hints he had a worryingly suggestive 48 hours with Justin Bieber

Odd B-Day Celebration

Diddy has guests partake in food from a nude lady at a lavish party, which suggests upsetting ideas about how this guy even celebrates his b-day.

Drunken Podcast Pressure

While under the influence on a podcast, Diddy coerces guests to participate in his freakish party antics, making the guests awkward.

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