Diddy predicted he would one day be arrested because of his wild parties while speaking with Entertainment Tonight in 1999.

Diddy predicted he would one day be arrested because of his wild parties while speaking with Entertainment Tonight in 1999.Entertainment Tonight

Sean “Diddy” Combs had a prescient moment over two decades ago when he predicted his wild parties would one day get him arrested.

The 54-year-old “Act Bad” rapper, who was booked Sept. 16 on federal charges including sex trafficking and racketeering, discussed in a resurfaced 1999 “Entertainment Tonight” interview how his bacchanals — central to the federal case against him — would “probably” land him behind bars.

“They won’t even give me a permit for the parties. And they don’t want me to throw the parties no more,” Combs said during a conversation about how his parties are, as the interviewer described it, “the hottest ticket around.”

“But we ain’t going to stop. We gonna keep on having fun. Bringing people together from all walks of life.”

Diddy predicted he would one day be arrested because of his wild parties while speaking with Entertainment Tonight in 1999.
Diddy predicted he would one day be arrested because of his wild parties while speaking with “Entertainment Tonight” in 1999.Entertainment Tonight

Diddy said "we ain't going to stop."
Diddy said “we ain’t going to stop.”Entertainment Tonight

“You’re going to hear about my parties,” he added. “They gonna be shutting them down. They gonna probably be arresting me – doing all types of crazy things just because we want to have a good time.”

In an unsealed federal indictment against Combs, prosecutors allege the music mogul held “freak off” parties where he would lure female victims to engage in sexual acts with male sex workers, plying the women with illegal drugs and recording videos of the performances that could later be used for blackmail.

“You know, whenever you bring up a different element into people’s environment, things that are brought and people’s around, people get intimidated,” Combs also told “ET.”

Sean "Diddy" Combs and his defense lawyers Marc Agnifilo and Teny Geragos are seated during a bail hearing in federal court in the Manhattan borough of New York City, U.S., September 18, 2024.
Combs and his defense lawyers at a bail hearing in Manhattan Sept. 18.REUTERS

“So a lot of people out there that feel intimidated by it, and it ain’t nothing but breaking down racial barriers; breaking down generation barriers. People from all walks of life. Ron Perlman talking to Jay-Z; Jay-Z talking to – you know what I’m saying?”

He continued, “It just goes on and on. You know, it’s just, it’s just like people from all walks of life connecting it, getting together.”

Sean 'Diddy' Combs and Justin Bieber attend the Ciroc party at Vanquish Lounge on February 5, 2014 in Atlanta, Georgia.
Combs and Justin Bieber attend the Ciroc party at Vanquish Lounge in 2014 in Atlanta.FilmMagic

L-R) Drake, Sean 'Diddy' Combs' and Rick Ross attend Sean 'Diddy' Combs' Ciroc The New Years Eve Party at his home on December 31, 2013 in Miami Beach, Florida.
Drake, Combs and Rick Ross Dec. 31, 2013, in Miami.WireImage

When asked how it made him feel knowing that invites to his parties were highly sought after, Diddy replied, “I mean, it’s cool, you know, it doesn’t make me feel any way. It doesn’t make me feel like a bigger person.”

He added, “It just makes you feel like I know how to throw a party.”

https://x.com/etnow/status/1838267458685407707
In addition to alleged “freak off” parties, Diddy hosted other more publicized lavish gatherings, such as his famous Hamptons White Party.

Over the years, that event and others were attended by the hottest celebs, including Leonardo DiCaprio, Beyonce, Jay-Z, Jennifer Lopez, Drake, Justin Bieber, Russell Simmons, Aaliyah, Paris Hilton, Kim Kardashian, Mariah Carey, Nick Cannon, Howard Stern, Kelly Osbourne, Aretha Franklin, Martha Stewart, Tommy Lee, Pamela Anderson, Vera Wang and more.

However, there is no evidence to suggest any of the celebrities at Diddy’s parties knew about or participated in alleged drug use, orgies, or “freak off” performances.

Sean "Diddy" Combs with industry lawyers and businessmen at his annual Labor Day White Party on Sept. 4, 1999.
Combs with industry lawyers and businessmen at his annual Labor Day White Party in 1999.ZUMAPRESS.com

Leonardo DiCaprio (back center) and Sean ''Diddy'' Combs.(front center) relax with friends at Diddy's Labor Day White Party at his house in East Hampton, New York on August 29, 1998.
Leonardo DiCaprio and Combs relax with friends in East Hampton in 1998.ZUMAPRESS.com

Diddy’s resurfaced interview is one of many interviews the rapper gave in years past that are now coming under renewed scrutiny.

In 2002, the “Bad Boy for Life” star joked with Conan O’Brien about locking women inside his parties, telling the late-night host, “A lot of ladies drink water at parties, so if you don’t have what they need, they’re going to leave. Got to keep them there, you need locks on the doors.”

Beyonce, Jay-Z, Kanye West, Kim Kardashian, Sean 'Diddy' Combs and Cassie celebrate their 2016 MTV Video Music Awards After Party at Pasquale Jones on August 28, 2016 in New York City.
Beyonce, Jay-Z, Kanye West, Kim Kardashian, Combs and Cassie at a 2016 MTV Video Music Awards after-party in New York City.GC Images
He added that he would turn off the air conditioning to keep the women “comfortable and loose.”

Combs is currently detained at a federal detention facility in Brooklyn while he awaits trial. He has pleaded not guilty to all charges.