Photos of Diddy's Miami Birthday Party From 20 Years Ago Resurfaces

Photos of the party show Diddy, Will Smith, Diana Ross, and other celebrities enjoying the festivities.

by · The Root
Photo: Alejandra Villa/Newsday RM (Getty Images)

The more time Diddy sits behind bars, the more details of his past life are revealed. Most recently, photos of his Miami birthday party from 20 years ago were obtained by TMZ, and it shows several well-known celebrities enjoying themselves with the hip-hop mogul.

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Some of the guests seen in the photos of the party include Will Smith, Diana Ross, Vivica A. Fox, Owen Wilson, Bruce Willis and Evan Ross. If only they knew the things the Bad Boy Records founder would be accused of years later.

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While the party initially looks innocent, one of the photos shows Diddy and his guests eating food off a naked woman, who acts as the centerpiece of a food platter. Despite the human food platter, none of Puff’s celebrity guests looked bothered.

It’s unclear if this party was one of the many alleged “freak-offs” Diddy was hosting over the years, but the image of a naked woman served as a food platter does not help. Take a look for yourself. Here are some of the photos from the event:

Photo: Backgrid
Photo: Backgrid
Photo: Backgrid
Photo: Backgrid

On Monday, Sept. 16, the 54-year-old rap mogul was arrested in Manhattan by federal authorities. His indictment was unsealed the following morning, revealing charges of racketeering conspiracy, sex trafficking and engaging in interstate transportation for prostitution. The allegations against Combs include sexual abuse, physical abuse, bribery and various drug offenses.

The most notable claims stem from his so-called “freak off” sex parties, where prosecutors allege women and men were drugged and forced to perform sexual acts at Combs’ pleasure. He was also accused of using video footage to blackmail the victims into compliance.

Combs’ arrest was roughly six months after federal authorities raided his two homes in Los Angeles and Miami in March 2024, and four months after damning video footage leaked of him brutally assaulting ex-girlfriend and Bad Boy Records signee Cassandra “Cassie” Ventura at a hotel in 2016.

In November 2023, Combs was sued by Ventura in a civil suit that accused him of sex trafficking, human trafficking, sexual battery, sexual assault, and other allegations. Combs quickly settled the suit within 24 hours, but lawsuits from other associates have quickly followed in the months since.

While many of the suits since 2023 have been civil, this federal case has Combs facing criminal charges. He has pleaded not guilty and was denied bail.

As we wait for more developments check out our previous coverage on Combs’ case:

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