Behind Diddy’s lavish, flashy parties are secrets about the rapper’s wild life. It is known that about 1,000 people attended these parties. 

Sean Combs (Diddy) faces life in prison if convicted under an indictment in the Southern District of New York on charges of conspiracy to commit extortion, sex trafficking and transportation to engage in prostitution. He has pleaded not guilty.

Host Sean “Diddy” Combs appears at “The Real White Party” at Combs’ East Hampton estate on September 2, 2007 in East Hampton, New York. Bryan Bedder/Getty Images

The case also sheds light on Combs’s former lifestyle, which included “Freak Offs,” the nickname Combs used to describe elaborate sex acts in which he allegedly drugged and coerced victims into performing prolonged sex acts with male prostitutes, beginning around 2009, according to the indictment.

The indictment has sparked discussion about the contrast between Combs’ cultural influence at his peak, such as the Great White Parties he hosted from 1998 to 2009, and his alleged behavior behind closed doors in later years.

A general view of the White Party hosted by Sean “Diddy” Combs and Ashton Kutcher to raise awareness for the No More Malaria campaign in 2009 in Beverly Hills, California. Jason Merritt/Getty Images

‘Modern Gatsby’

Combs reportedly began hosting the annual parties in 1998 to mark his presence in New York’s exclusive Hamptons community. His dream was to blend his hip-hop lifestyle with the East Coast elite and “take away everyone’s image and put us all on the same page and on the same level,” Combs told Oprah Winfrey in a 2006 interview.

“My party had the craziest mix: some of the guys in my party were from Harlem; Leonardo DiCaprio, after he had just finished filming the 1997 blockbuster ‘Titanic,’” Combs said. “My party had upscale people and relatives from the South. There were 200 people sitting here, just for the cookout.”

Khloe Kardashian at the Combs White party in 2009. Chris Weeks/Getty Images

For his part, Combs clearly envisioned himself as a modern-day Jay Gatsby, the fictional character in F. Scott Fitzgerald’s 1925 novel “The Great Gatsby,” a millionaire living on Long Island and played ironically by Leonardo DiCaprio in the 2013 film adaptation.

‘Icon’

Since their inception, these parties have been very popular, attracting many entertainment talents and industry giants.

According to THR, the original guest list was said to have been as large as 1,000 people, all of whom were required to wear white. Martha Stewart, a guest at Combs’ first party, told THR in 2018, “It was amazing to see the entire party dressed in white.” Socialite and businesswoman Paris Hilton described the first event as “iconic and everyone was there.” CNN has reached out to reps for Stewart and Hilton for comment.

Paris Hilton at Sean “Diddy” Combs’ White Party – Inside Nikki Beach in St Tropez, France. Stuart Morton/WireImage/Getty Images

The parties expanded from a Labor Day event to a Fourth of July celebration and changed locations to include Los Angeles and Saint-Tropez.

Combs used several parties to raise funds for various causes he supported, demonstrating his social influence at the time.

GQ reported in 2016 that : “The party seemed to get bigger as corporate sponsors joined in, and Combs used it to launch perfumes, vodkas, and even charitable endeavors.”

“The last official White Party on record, in 2009, took place in Los Angeles,” the publication reported. “But in essence, Puff Daddy [Combs]’s White Party was the barbecue to end all barbecues, capturing a piece of pop culture that’s incredibly intertwined today.” Photos taken over the years show generations of guests attending.