Hollywood stars who moved in Sean ‘Diddy’ Combs’ circles

Diddy was the enthusiastic music mogul whose “White Parties” were legendary in Hollywood. Take a look at the celebrities who once called him a friend.

He was the enthusiastic music mogul whose “White Parties” were legendary in Hollywood.

Anyone who was anyone would attend Sean “Diddy” Combs A-list events at his lavish Hamptons and Miami mansions.

But the party is now over for the 54-year-old rapper, who faces 120 sex trafficking and racketeering lawsuits.

As he languishes in a New York jail awaiting trial, we look at the celebrities who once moved in Coombs’ circles – and considered him the unofficial king of the entertainment industry.

None has been implicated in Combs’ alleged crimes, nor accused of any wrongdoing – indeed most have gone to great pains to distance themselves.

They were the actors, musicians, royals and sporting stars who once called him a friend.

CASANDRA “CASSIE” VENTURA

In November last year, singer Cassie Ventura filed a lawsuit against her ex-partner, Combs, accusing him of sexual slavery and rape.

Ventura alleged in her lawsuit that Combs hired a man on whom she would perform sexual acts while the rapper “watched and masturbated”.

She said Combs referred to the arrangement as a “Freak Off” or “FO” and that she found the locations and hired the sex workers whenever Combs told her he wanted to engage in a “Freak Off”.

Just one day later, the lawsuit was settled without admission.

Combs and Ventura arrive at the Met Gala on May 7, 2018, at the Metropolitan Museum of Art in New York. Picture: AFP

Ventura met Combs in 2005 – she was 19, he was 37 – and was signed to his label, Bad Boy Records.

She had claimed in the court proceeding that she was lured into a “fast-paced, and drug-fuelled lifestyle, and into a romantic relationship with him” and that Combs raped and beat her.

She also alleged he forced her into sex trafficking. Combs had vehemently denied the allegations.

Separately, he was forced to apologise when CCTV was broadcast by CNN showing him brutally assaulting Ventura in a hotel corridor.

JENNIFER LOPEZ

Jennifer Lopez and Combs were once an A-list couple in Hollywood. The pair dated from 1999 to 2001 after meeting on the set of Lopez’s video for the song If You Had My Love.

In a 2003 interview, Lopez explained why their relationship ended, saying: “I never caught him [cheating] but I just knew. He’d say he was going to a club for a couple of hours and then never came back that night. I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?”

The pair pictured in December 1999. Picture: AP Photo/Don/Pollard

In recent days, Lopez was accused by her first husband Ojani Noa of attending Combs’ parties.

In a post on Instagram, he shared a “Diddy party guest list” – which was filled with celebrity names – and numerous photos of Lopez and Combs at his “white parties”.

Noa captioned the post with: “I’M NOT ON THE LIST. To those people and media outlets asking if I ever went (to) that Piece of Sh*t (DIDDY’S) Parties. No and No. Never. But my Ex-Wife (Jennifer Lopez) a.k.a (JLO) Did.. Ask Her.

As of right now, neither Lopez or her representatives have responded to these claims.

JUSTIN BIEBER

A baby-faced Justin Bieber rose to fame with his song Baby when he was just 15 years old. Soon, he was bumping shoulders with big names, including Combs. The two hung out several times.

Combs, Bieber and Rick Ross attend Ciroc party at Vanquish Lounge on February 5, 2014 in Atlanta, Georgia. Picture: Prince Williams/FilmMagic

In resurfaced footage of the pair, Combs says to the camera, “[Bieber’s] having 48 hours with Diddy, where we hanging out and what we’re doing we can’t really disclose. But it’s definitely a 15-year-old’s dream. I have been given custody of him. He’s signed to Usher when he did his first album. I don’t really have legal guardianship of him, but for the next 48 hours he’s with me. And we’re gonna go buck fool crazy.”

In another video, the pair are shown years later shaking hands cordially. Bieber tells Combs he is “all good”.

“Everything’s good? Selling out arenas and everything?” Combs asks him. “Starting to act different, huh? You ain’t been calling me and hanging out the way we used to hang out.”

CHRIS BROWN

Chris Brown denied new claims in a recently-aired documentary called Chris Brown: A History of Violence that he drugged and raped a woman on Combs yacht in December 2020.

The woman alleged in the piece, which premiered on the US’s true crime network, Investigation Discovery, that Brown handed her “drink after drink” and she started feeling sleepy.

She found herself in a room with the rapper. “I remember I did lay back and I’m like, ‘Why can’t I get up?’ Next thing I know he was on top of me and I couldn’t move and I said ‘no’ and then I felt him … next thing I knew he was inside me,” she said.

Combs and Brown attend the White Party hosted by Combs and Ashton Kutcher to help raise awareness for Malaria No More held at a Private Residence on July 4, 2009 in Beverly Hills, California. Picture: Jason Merritt/Getty Images

The woman’s lawyer, Ariel Mitchell, confirmed to The Hollywood Reporter that she is representing her client again after a lawsuit was withdrawn in 2022 due to text messages her client had sent to Brown surfacing. The woman had denied they had existed.

“I stand by her then and now. This was not a question of the veracity of her claims. It was just how she neglected to provide us all of the requested evidence,” Mitchell said.

JAY-Z AND BEYONCE

The friendship between the A-list couple and Combs goes back several years, with Jay-Z and Beyonce attending several of Combs’ infamous “white parties”.

By association alone, people have commented about the couple and their relationship with the rapper.

Combs and Beyonce and Jay-Z attend the Sean Jean/Zac Posen CFDA after-party at Marquee, on June 7, 2004 in New York City. Picture: Evan Agostini/Getty Images

Recently, TV presenter Piers Morgan was forced to apologise after a guest on his show Uncensored said she had been “screaming that Diddy and Jay-Z are monsters for four years”.

The guest, singer Jaguar Wright, had no evidence of Jay-Z or Beyonce’s involvement in any of Combs’ alleged crimes.

Morgan was contacted by Jay-Z and Beyoncé’s lawyers, who said the claims were “totally false and have no basis in fact”.

“Editing interviews is not something we do lightly at a show called Uncensored,” Morgan said in his apology. “But like the proverbial cries of ‘fire’ in a crowded theatre, there are legal limits on us, too. And we apologise to Jay-Z and Beyoncé.”

LEONARDO DICAPRIO

After a 1998 picture of a young Leonardo DiCaprio smoking and laughing at one of Combs’ parties emerged, the actor has come under fire for being friends with the rapper.

Even though DiCaprio and Combs have not been seen together in many years, DiCaprio’s recent endorsement of Harris brought to the fore Combs’ connection to A-lister Democrat supporters.

DiCaprio has come under fire for attending one of Combs’ white parties. Picture: Frazer Harrison/Getty Images

“Climate change is killing the earth and ruining our economy,” he said in an Instagram video. “We need a bold step forward to save our economy, our planet and ourselves. That’s why I’m voting for Kamala Harris.”

Comments included, “Another avid Diddy party attendee coming out to support Kamala.”

50 CENT

Curtis “50 Cent” Jackson has had “beef” with Combs for several years.

In 2006, Jackson released his diss track “The Bomb” which accused Combs of being involved with the 1997 murder of the Notorious B.I.G. Combs denied the accusations and has not been charged with the crime.

The pair have traded barbs over the years, culminating in a Netflix docuseries being produced by Jackson about the charges against Combs.

Rappers 50 Cent, Kanye West, Combs, and Jay Z perform onstage during Screamfest '07 at Madison Square Garden on August 22, 2007 in New York City. Picture: Scott Gries/Getty Images

“This is a story with significant human impact. It is a complex narrative spanning decades, not just the headlines or clips seen so far,” Jackson and director Alexandra Stapleton told Variety.

“We remain steadfast in our commitment to give a voice to the voiceless and to present authentic and nuanced perspectives. While the allegations are disturbing, we urge all to remember that Sean Combs’ story is not the full story of hip-hop and its culture. We aim to ensure that individual actions do not overshadow the culture’s broader contributions.”

USHER

When Usher was 15, he was sent to live with Combs in 1994 to work on his debut album.

The singer has described the experience as eye-opening, specifically mentioning being introduced to sexual activities in Combs’ home.

However, despite this, Usher has stayed largely quiet about the details of his time with Combs, although he once remarked that he wouldn’t send his kids to live with him.

Singer Usher with Combs pose backstage in 2004. Picture: Getty Images

Usher has not commented on Combs’ arrest or allegations, however, in an interview in 2016 with radio star Howard Stern he said: “There was always girls around. You’d open a door and see somebody doing it, or several people in a room having an orgy.”

THE TRUMPS

Former President Donald Trump once referred to Diddy as a “good guy” during an episode of The Apprentice, suggesting a longstanding friendship between the two entrepreneurs.

In 1997, Mr Trump and his ex-wife Ivana attended the US Open with Combs, and that same year, Mr Trump was present for the opening of Combs’ restaurant.

Throughout the 2000s, they were seen together at various galas and charity events. Tiffany Trump also attended the 2009 White Party with her mother, Marla Maples, who noted how the gathering of “all these beautiful people in white” felt like stepping into another dimension.

PARIS HILTON

Paris Hilton was a regular at Combs’ gatherings, spotted celebrating alongside Nicole Richie at his 35th birthday and dancing at his White Parties in 2003 and 2006.

Paris Hilton was a regular at Diddy’s gatherings. Picture: Getty Images

At the 2006 event in Saint Tropez, she posed on a bed with a then-unknown Kim Kardashian and Combs, a photo that has since garnered attention following the rapper’s arrest.

In a 2017 Instagram post, Hilton shared, “Had such an epic time at Diddy’s house party last night!”.

And in 2022, she told Ellen DeGeneres that the best party she had ever attended was “Puffy’s 50th birthday; it was so sick.”

Originally published as Hollywood stars who moved in Sean ‘Diddy’ Combs’ circles