Explaining Diddy’s long history with Leonardo DiCaprio as shocking freak-off video resurfaces

There’s an old video being reshared on Twitter that shows Diddy talking about Leonardo DiCaprio attending his parties, and it has reignited speculation around the actor’s part in the rapper’s now-infamous freak-offs.

The video, which has racked up over 10 million views across numerous posts, showed Diddy talking about his “favourite” celebrity on his invitation list. He said Leonardo DiCaprio, leading many people to assume that the Hollywood actor attended the freak-off parties we’ve heard so much about.

“Please be AI,” one person begged in the comments, as another said, “There’s always something linking Leonardo to awful people, but he never gets accused of a crime.”

Here’s everything we know about Leonardo DiCaprio and Diddy’s former friendship, and whether or not he actually ended the infamous parties.

Old video of Diddy saying Leonardo Dicaprio is his favorite guest at his parties is resurfacing😬 pic.twitter.com/V5doOjCzyO

— kira 👾 (@kirawontmiss) December 10, 2025

Leonardo DiCaprio and Diddy were friends at one point

After Diddy was arrested in 2024 on charges of racketeering, sex trafficking and trafficking to engage prostitution, most of which he was cleared of, pictures started circling of Leonardo and Diddy at various celebrity bashes.

One such picture was taken during one of Diddy’s white parties at his home in East Hampton. Leo, who was 24-years-old at the time, was seen sitting amongst Diddy and other friends dressed in head-to-toe white.

Credit: Matt Campbell/EPA/Shutterstock

Leo was pictured with Diddy a few times over the subsequent years. He spent time with the disgraced rapper at the Democratic National Convention in 2004 and was pictured dancing with Diddy at his 50th birthday in 2019.

The video that is again being reshared was from Diddy’s 73 Questions with Vogue from 2018.

Leo addressed the controversy during Diddy’s trial

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Credit: Globe Photos/Shutterstock

When Diddy was at trial last year, which resulted in him getting just four years behind bars, someone close to Leonardo DiCaprio addressed the lingering questions about their connection.

They told the MailOnline: “Leonardo DiCaprio has absolutely nothing to do with any of this. He attended a few of his parties back in the early 2000s – but literally everyone did. They were not freak-offs. They were big house parties. Leo was at the start of his career at the time and has moved way past his partying.

“He has nothing to do with any of that world, so for anyone to assume that he will get roped into this based on a few grainy photos that are more than 20 years old is ridiculous. Leo is focused on his career and his relationship and is not at all thinking about Diddy’s federal case, which he has nothing to do with.”

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Featured image credit: Globe Photos/Shutterstock