As the spotlight shines on the Bad Boys CEO, we’re taking a look at some of the celebrities who have been linked to him over the years.

Usher

 

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Usher met Diddy as a teenager and even lived with him for a year, an experience dubbed “Flavor Camp.” Reflecting on his time at Diddy’s home, Usher reportedly described it as “pretty wild” during an appearance on the Howard Stern show. “I went there to see the lifestyle,” he said, reports the Daily Star.

“And I saw it. But I don’t know if I could indulge and understand what I was even looking at. It was pretty wild…. It was crazy.”

When asked if he’d send his own children to the “camp,” Usher replied: “Hell no.”

 

Interestingly, around the time of Diddy’s arrest, hundreds of Usher’s X/Twitter posts vanished, with the singer claiming to fans that his “account got hacked.”

Jay-Z

 

( Image: Getty Images for Sean Combs)

Jay-Z’s connection with Diddy runs deep, as the two music moguls have not only worked together musically, but also discussed potential business ventures.

In 2015, Diddy even mentioned, “Me and Jay we’ve talked about it. We said we want to pick the best one.”

However, Jay-Z has kept mum regarding the recent allegations and arrest of Combs, a silence that rapper 50 Cent has highlighted in several online posts.

Ashton Kutcher

 

( Image: Getty Images)

Ashton Kutcher, known for his Hollywood charm, has been seen at Diddy’s events and considers him a friend. Recalling the start of their friendship during a Hot Ones interview, Kutcher shared, “It started over Punk’d because he was like, ‘Yo, you can’t punk me! ‘ I was like, ‘I don’t know what to tell you, everybody is on the table.’ He’s like, ‘Not me, I’m off the table.’ That started our conversation. We became fast friends and we used to just hang out, watch football together.”

Khloe Kardashian

 

( Image: Getty Images)

Khloe Kardashian, along with her famous family, has partied with Diddy. She revealed on an episode of Keeping Up With The Kardashians about a wild experience at one of his parties, telling her sister, Kourtney: “I got on a plane at 5:30am. Well, this party… I think half the people there were butt naked.”

“You would have loved it,” she joked, hinting at the fun had behind closed doors. Listed among the A-list attendees was none other than Justin Bieber.

Paris Hilton

 

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Paris Hilton, the illustrious hotel heiress, is no stranger to exclusive gatherings. When questioned on Ellen DeGeneres’ talk show about her best party experience, she buzzed: “Puffy’s 50th birthday. It was so sick. Epic.”

Having been spotted at a multitude of Diddy’s shindigs, with his iconic 50th birthday bash held as recently as 2020, Paris makes the high-profile party scene look effortless.

Ray J

 

( Image: Getty Images North America)

Ray J, the smooth singer-songwriter, holds a longstanding friendship with Diddy. While chatting on NewsNation’s CUOMO, he disclosed: “We’ve never seen the stuff that’s being said and the stuff that people are finding out, like, I’ve never been in rooms that people are talking about and I never knew they existed.”

Jennifer Lopez

 

Diddy and JLo ( Image: Getty Images)

Jennifer Lopez, with her stardom blazing, once shared an illustrious romance with Diddy from 1999 through 2001. The duo found themselves entangled in a nightclub shooting incident during their time together.

Although arrested, Lopez quickly regained her freedom while Diddy faced and later triumphed over weapon possession and attempted bribery accusations originating from the same event.

Additionally, J.Lo has expressed past grievances of being “manhandled” in relationships within her Netflix documentary, not pointing fingers at any particular ex.

Leonardo DiCaprio

 

Sean Combs and Leonardo DiCaprio ( Image: Getty Images)

Titanic star Leonardo DiCaprio has been seen at Diddy’s bashes in the past, including the famous white party during his younger years. However, a source recently told the Daily Mail that Leo hasn’t been in touch with Diddy for quite some time, indicating a distance between the actor and the rapper.

50 Cent

 

Sean Diddy Combs, Paris Hilton and 50 Cent .

Rapper 50 Cent is known for not attending Diddy’s gatherings. “I’ve been very vocal about not going to Puffy parties and doing s*** like that,” he shared with the Hollywood Reporter. “I’ve been staying out of that s*** for years. It’s just an uncomfortable energy connected to it.”

He also once mentioned feeling “uncomfortable” around Diddy after being invited on a shopping trip due to a clash in energies.

Aubrey O’Day

 

Aubrey O’Day and Diddy .

Aubrey O’Day, a former member of Danity Kane – a band formed by Diddy on the MTV show Making the Band 3, later alleged that the band split because “I wasn’t willing to do what was expected of me.”

“He fired me,” she revealed on the Call Her Daddy podcast.

On the Off The Vine with Kaitlyn Bristowe podcast, Aubrey claimed: “I was fired on national television for being overly raunchy and promiscuous. That’s actually like wrongful termination. That’s a lawsuit against a lot of people.”

She also said that while filming, Diddy would often tell her how much he despised her. But off-camera, he controlled everything about her appearance, down to her toenails.

Justin Bieber

 

Diddy and Justin Bieber

Justin Bieber reminisced about his early career connections with the rapper, sharing on Instagram: “I remember going to my brother Diddy’s office to pitch him a song I wrote for him when I was like 14, sadly the song was trash haha. And it would be a hard no from him, fast forward to a few years ago Puff asked if I would freestyle something for his upcoming Love album. Wild full circle moment, love you @diddy.”

 

Concerns have risen among fans as old footage resurfaced, showing a young Bieber at parties with Diddy, alongside Bieber’s own references to challenging “encounters” in the industry.

Kid Cudi

 

Kid Cudi

Kid Cudi, who previously dated Diddy’s ex Cassie Ventura, is also caught up in the whirlwind of allegations against the I’ll Be Missing You rapper. Ventura filed a lawsuit last year accusing Diddy of “trapping” her in a “cycle of abuse, violence, and sex trafficking,” which he has denied.

Reports suggest that the lawsuit included claims of Diddy threatening to destroy Kid Cudi’s car, which was allegedly set ablaze between 2011 and 2012. While Diddy hasn’t directly responded to these specific allegations, he has refuted Ventura’s accusations against him broadly.