We delve into Leonardo DiCaprio and Sean ‘Diddy’ Combs’ twenty year friendship – and the celebrity-filled White Parties

Named as P Diddy’s favourite ever party guest, Leonardo DiCaprio’s former friendship with the rapper has been called into question after his sex trafficking arrest.

The superstar pair have enjoyed several get togethers over the decades. From Diddy’s infamous White Parties at his Hamptons mansion, to the I’ll Be Missing You musician’s 50th birthday party in 2019 – the men appeared to have a close friendship.

The Titanic star was first pictured at one of Diddy’s soirees in 1998, where Leo could be seen drinking champagne and smoking among other celebrity guests.

Leo DiCaprio
Leonardo DiCaprio parties with P Diddy at one of his infamous White Parties in 1998 ( 
Image:
Globe Photos/REX/Shutterstock)

In a resurfaced video for 2017, Diddy proudly describes the Oscar winner as his “number one person” on his White Party invitation list.

In 2019, Leo joined a host of big names at Diddy’s Beverly Hills mansion to celebrate the rapper’s 50th birthday. He was spotted on the dance floor wearing a baseball cap and blazer.

P Diddy
Diddy and Leo at the Democratic National Convention in Boston ( 
Image:
WireImage for Citizen Change)

Diddy
The A-list pair have been spotted together several times over the past 20 years ( 
Image:
Getty Images)
They were also pictured together at the Democratic National Convention in 2004, and an NBA All-Star Game in LA the same year.

Since Diddy’s arrest, Leo, 49, has distanced himself from Sean ‘Diddy’ Combs.

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A source told the DailyMail that Leo has “not been in contact” with Combs for years and that he never took part in the “freak offs,” and has nothing to do with Diddy’s case.

“Leonardo DiCaprio has absolutely nothing to do with any of this,” said the source. “He attended a few of his parties back in the early 2000s – but literally everyone did.”

Leo is not the only A-list names to have enjoyed partying at Diddy’s annual white-themed bashes. Others have included Ashton Kutcher, Jay-Z and Beyonce, Mariah Carey, Russell Brand, Kelly Osbourne Tommy Lee, Pamela Anderson and Paris Hilton. Jennifer Lopez, who dated Diddy from 1999 – 2001, was also snapped attending his parties.

Music industry insider Tom Swoope has claimed that Diddy’s parties, which he attended, had different “tiers” of access -Diddy is accused of demanding sexual humiliation acts on the promise of money or record deals. Swoope and other alleged witnesses have also claimed that drugs including cocaine and ecstasy were being snorted off surfaces which included the bodies of guests.

Back in 2006, Diddy told Oprah Winfrey he designed his White Party to integrate the world of hip-hop with that of the super-rich, telling her: “I wanted to strip away everyone’s image and put us all in the same colour and on the same level.”

But Swoope has alleged that the events provided more of a power trip for Diddy than anything else. Combs, 54, was arrested last week and indicted in the Southern District of New York on charges of racketeering, sex trafficking and trafficking to engage prostitution.

The rapper is accused of forcing women into ‘elaborate and produced sex performances’, described as ‘freak offs’. A thousand bottles of baby oil were found during searches of his properties, it is claimed.