A look at Sean 'Diddy' Combs' social circle of celebrity friends

From supermodels to singers, social media stars and significant members of the British monarchy, it's fair to say Sean 'Diddy' Combs has enjoyed numerous high profile friendships over a decades-spanning career. 

But his place in the higher echelons of the celebrity stratosphere has been significantly compromised following his arrest and indictment on charges ranging from sex trafficking to forced labour, kidnapping, arson, bribery, and obstruction of justice.

As of Thursday, the wealthy rapper and producer responsible for defining east coast hip hop in the 1990s is languishing in jail, his reputation in tatters and his career hanging precariously in the balance. 

So serious are the allegations aimed at Combs, he has been compared to notorious billionaire sex trafficker Jeffery Epstein, who committed suicide by hanging in 2019 while housed at New York's Metropolitan Correctional Facility on federal charges of trafficking minors. 

The rapper has been accused of hosting sordid sex parties, referred to as 'freak offs,' during which it has been alleged his victims would be drugged, forced to have sex for days on end, and left with such severe injuries they needed weeks to recover. 

He has pleaded not guilty to all of the charges he faces.  

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Speaking to the NYP, an unnamed federal source said if you were attending and participating in his sex parties 'you were being recorded from every possible angle, including angles you wouldn’t have known about'.

According to the bombshell indictment, Combs allegedly forced women - some of whom were still teenagers - into days-long drug-fueled orgies.

He allegedly arranged and directed the sex parties, while masturbating throughout the performance and supplied women drugs such as ecstasy, ketamine, and BHB to keep them energized, federal prosecutors said.

The indictment added: 'After freak offs, Combs and the victims typically received IV fluids to recover from the physical exertion and drug use'.

Prosecutors said that the music mogul's employees covertly booked hotel rooms for the 'freak offs', while stocking them with baby oil, lubricant, and extra bed sheets. 

But the federal source told the news site that following their thorough raids, they unearthed evidence that revealed the women didn't feel like they were free to go, adding video evidence showed women who were 'clearly out of it' while having sex with the men.

Combs would often tape the 'freak offs' to use as leverage to silence the women, and was known to choke, shove and throw people to the ground, prosecutors added.

'The sensitive, embarrassing and incriminating recordings that he made during Freak Offs as collateral to ensure the continued obedience and silence of the victims,' the indictment said.

So what of Combs' lengthy list of celebrity friends? While there is no suggestion that any have participated in illegal or sordid activities with the rapper, many have partied with him down the years. 

1. 

Justin Bieber

Bieber's relationship with the music mogul goes back to the latter’s teens, when he was discovered as a budding YouTube artist by Scooter Braun and R&B star Usher. 

Footage of Combs with a then 15-year-old Bieber has resurfaced online after the rapper was arrested on sex-trafficking charges.

X/Twitter users have branded the footage 'creepy', in which sees Diddy, who is 24 years older than Bieber, documents his '48 hours' staying with the young singer.

In the clip, Combs stands next to the young pop sensation and tells the camera: 'He'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.'

The hip hop mogul, 54, adds: 'I have been given custody of him. He's signed to Usher and I had legal guardianship of Usher when he did his first album.'

Diddy continues: 'I don't have legal guardianship of him [Bieber] but for the next 48 hours he's with me and we're gonna go full crazy.' 

Bieber, now 30, is said to be so deeply 'disturbed' by the news of Combs' arrest on that he's cut himself off from the world.

Speaking exclusively to DailyMail.com, an insider said that the new dad has been completely 'thrown' by the harrowing allegations and is grappling to make sense of them - especially given that he collaborated with Combs less than a year ago.

The source said of the fragile singer: 'Bieber is so disturbed by the Diddy news and is unwilling to process it or discuss it so he has shut off.

'So many people who helped to make him who he is were very close to Diddy and it has completely thrown him.

'Justin hasn't been responding on this since the home raids. He's not going to.'

The insider added that Bieber also deeply regrets having collaborated with the disgraced mogul last year, and would never have done so had he known the allegations that have since come to light.

They continued: 'He had a long break from Diddy when he believes most of this took place and he had distanced himself from him.

'He was featured on Diddy's most recent album, and had he known any of this, there is no way he would have done it.'

2. Usher 

Usher himself has claimed he was exposed to some 'pretty wild' stuff while living with Diddy aged 14.

In an unearthed interview from 2016, the Burn singer revealed details about his time living with Diddy in the spring of 1994.

While appearing on The Howard Stern Show, Usher, 45, alleged that it was record producer L.A. Reid's idea to have him live with the R&B singer in Scarsdale to 'see the lifestyle'.

When asked if Diddy's 'place was filled with chicks and orgying nonstop' by Stern, Usher replied: 'Not really... I got a chance to see some things … I don't know if I could indulge and even understand what I was looking at.

'It was pretty wild. It was crazy. There were very curious things taking place and I didn't necessarily understand it,' he admitted.

As for whether he would send his children to 'Puffy Flavor Camp,' Usher responded with an emphatic: 'Hell no!'

Back in 2004, Usher told Rolling Stone that Diddy introduced him to 'a totally different set of s**t — sex, specifically.'

'Sex is so hot in the industry, man,' he continued. 'There was always girls around. You'd open a door and see somebody doing it, or several people in a room having an orgy. You never knew what was going to happen.'

3. 

Jennifer Lopez

Jennifer Lopez once revealed how Sean 'Diddy' Combs was the first man to cheat on her during their 'tumultuous' relationship from 1999 until 2001.

She later said she ended things because she didn't feel like she could have the family life that she dreamed of with the musician.

Lopez claimed he had cheated on her, telling Vibe magazine in 2003: 'It was the first time I was with someone who wasn’t faithful.

'I was in this relationship with Puff where I was totally crying, crazy and going nuts, it really took my whole life in a tailspin.

'I never caught him but I just knew. He’d say he was going to a club for a couple of hours and then never come back that night.'

The pair's romance first began while Lopez was preparing for the release of her debut album, On The 6, which Combs helped produce.

During their relationship, Lopez debuted her most famous outfit during the Grammy Awards ceremony in 2000. The green silk chiffon dress from Versace was super low-cut, barely covering her cleavage.

But the couple also hit headlines after Lopez and Combs were arrested on December 27, 1999, following a shooting outside the Times Square Club in Manhattan.

The two were charged with criminal possession of a weapon, though the charges were later dropped against her as she was determined to be uninvolved.

Lopez broke up with the rap mogul a month before his trial was slated to begin in 2001. He was ultimately acquitted on all charges. 

4. Kim Kardashian, Khloé Kardashian and Kylie Jenner

Kim and Khloé Kardashian were joined by half-sister Kylie Jenner as Combs' hosted an extravagant 50th birthday party at his $40million Holmby Hills mansion in 2019. 

Five years later the sprawling property would be raided by Homeland Security as part of a sex trafficking probe, but on that December night it played host to an array of celebrity friends. 

Record producer Stevie J recently shared a video of the event, which was attended by stars including the Kardashians, Beyoncé and Jay-Z, Snoop Dogg, Paris Hilton, Naomi Campbell and the late Kobe Bryant.

Posting the clip on social media, he wrote: 'This is what a real Diddy Party looks like.'

Other guests in attendance included Leonardo DiCaprio, Dr Dre, Kanye West, Pharrell Williams, Fergie, Mary J Blige and the Kardashian sisters sipping on Ciroc while celebrating the rapper's big day.

Nearly 600 guests in total wined and dined the night away, with music provided by DJ Cassidy. 

5. Naomi Campbell

The British supermodel has made numerous public appearances with Combs, a rumoured former love interest. 

A guest at his star-studded 50th birthday celebration, Campbell also helped his twin daughters Jessie and D'Lila celebrate their 16th birthdays in 2022. 

As recently as November 9, 2023 she was rubbing shoulders with Combs and Janet Jackson while hosting his 54th birthday at LAVO nightclub in London. 

And the good times continued in the back of a London cab, where Combs was seen sipping on a glass of wine before they left the birthday party separately.

The pair were rumoured to have dated back in 2001 but a representative for the star later confirmed they were just friends. 

Campbell and Jackson have since wiped the photos they shared from his 54th birthday from Instagram, according to Page Six. 

The move followed a lawsuit filed by Combs' ex-girlfriend Cassie Ventura, who accused him of controlling and abusing her for over a decade.

The singer alleged that during that time he beat her, forced her to do drugs and ordered her to have sex with multiple male prostitutes — while he watched and recorded the encounters.

A day after the lawsuit was filed, Page Six noted that images shared from his birthday party were scrubbed clean from their Instagram pages.

A source told Page Six: 'Losing people like Naomi and Janet - those types - it's going to be very hard on him, because he's such a narcissist.'

6. Prince Harry and Prince William 

It was 2008 when Combs famously met British royals William and Harry backstage at the Concert for the late Princess Diana's celebrity-packed after-show party.

The now estranged brothers posed for photos alongside Combs and Kanye West, with Harry throwing an arm across the jailed mogul's shoulder. 

West attempted to persuade the Princes to put on the oversized white stripy shades he was wearing, but they jokingly declined.