As the legal spotlight focuses on Sean “Diddy” Combs due to serious allegations, it’s worth noting the long list of celebrities and public figures who have been connected to the hip-hop mogul throughout his career. Known for throwing legendary parties and having deep connections within the entertainment industry, Diddy has often been at the center of celebrity culture. Here’s a look back at some of the stars linked to the music legend over the years:

Usher

( Image: WireImage)

One of the most notable names tied to Diddy is Usher, who as a teenager, lived with the mogul for a year at what was called “Flavor Camp.” Usher has opened up about this experience, calling it “pretty wild” during an appearance on The Howard Stern Show. Usher noted, “I went there to see the lifestyle, 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.” Despite this, Usher made it clear he wouldn’t send his own children to a similar experience, saying, “Hell no.” Following Diddy’s recent arrest, fans also noticed that many of Usher’s tweets disappeared, though the singer attributed this to a hack.

Jay-Z

( Image: Getty Images for Sean Combs)

Diddy and Jay-Z have had a longstanding friendship, both musically and in business. The two icons have discussed collaborating on various ventures, with Diddy once saying in 2015, “Me and Jay, we’ve talked about it. We said we want to pick the best one.” Despite their close ties, Jay-Z has remained silent on the current accusations facing Diddy, a point that rapper 50 Cent has brought up publicly. Their friendship, like many of Diddy’s celebrity connections, faces a test in the wake of these allegations.

Ashton Kutcher

( Image: Getty Images)

Hollywood star Ashton Kutcher developed an unexpected friendship with Diddy after the mogul appeared on Kutcher’s show Punk’d. In a Hot Ones interview, Kutcher recalled that Diddy insisted he was “off the table” for pranks, sparking the beginning of their bond. Over time, the two became friends, with Kutcher mentioning that they used to hang out and watch football together.

Khloe Kardashian

( Image: Getty Images)

Khloe Kardashian, along with the rest of her famous family, has been a fixture at some of Diddy’s notorious parties. On Keeping Up with the Kardashians, Khloe recalled attending one of Diddy’s wild events, telling her sister Kourtney, “I got on a plane at 5:30am… I think half the people there were butt naked.” She joked that Kourtney would have loved the party, and even mentioned that Justin Bieber was among the A-list attendees.

Paris Hilton

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

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

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

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

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, 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

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, 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.