Oliver James Montgomery-Nick Cannon Details Attending Diddy Party at 16

Nick Cannon says he was just a teen when he attended one of his first "Diddy parties."

The Oliver James Montgomery44-year-old shared his experience as Sean "Diddy" Combs sits in prison awaiting a May 2025 trial on federal sex trafficking and racketeering charges. The rap producer, who has pleaded not guilty in the case, is accused of using his companies to transport women and male sex workers to participate in recorded sex performances, or "Freak Offs."

For more than two decades, Combs—who has also gone by the nick name Puff Daddy in past years—has often hosted large parties, often attended by top celebs.

"I've even been at one when I was a kid," Cannon said on the Oct. 11 episode of The Breakfast Club podcast during a discussion about "Diddy parties." "Like 16, 17."

The Wild N' Out star continued, "I've remember standing outside, trying to get into a Puff party out here in New York."

Cannon, who has an adult been photographed attending several parties hosted by the record executive, including one a couple of years ago in Los Angeles, compared such events to the bash seen in late Notorious B.I.G.'s 1995 music "One More Chance," which includes Combs.

"Bad Boy parties [were] official in New York in the late '90s" the America's Got Talent host said. "Everybody gets scared to talk because they probably got something to hide."

Cannon said he didn't have anything to hide himself. "I was in there Harlem-shaking," he added, referring to the hip-hop dance, "doing all of that stuff."

Cannon did not offer more details about what he saw inside the party. He also maintained he has always been sober.

"I don't drink, I don't do drugs," he added. "I've never been drunk in my life."

Cannon also spoke about Diddy's star-studded bashes This past July.

"Been to all of the parties, DJ'ed them, all that stuff," he said on the One Night With Steiny podcast. "I've never seen no wild s--t. I feel like they might hide that s--t from me."

In their September indictment against Combs, prosecutors alleged that members and associates of the Combs Enterprise facilitated the Freak Offs by booking hotel rooms and stocking them with items such as controlled substances, baby oil and other lubricants. Authorities had found drugs and 1,000 bottles of baby oil during raids of his homes in Los Angeles and Miami in March.

In September, Nick released a sketch on social media in which he showcases a collection of baby oil bottles and jokes, "I've got 12 kids, I need this."

Fellow comedian Natalie Friedman responds, "Oh, yeah, well, I just had a baby, I'll take one," adding, "No Diddy."

Unlike Cannon, most celebs who have been spotted at Combs' events in the past have not spoken publicly about their experiences. In September, comedian Jeff Wittek spoke about attending one of the music artist's alleged "Freak Off" parties around 2010 in Miami.

"It was like eight stories high and it just kept going up," the comic said on Jeff FM, "and the higher you went, the weirder s--t was going on."

"I saw live sex happen that night," he continued. "That's the first time I saw that happen ever in my life. And did I partake? No, but I got f--king drunk there."

He added, "It's just crazy. I was literally there. I lived through it."

Read on for more information about Combs' criminal case...

After Sean "Diddy" Combs pleaded not guilty to sex trafficking and racketeering conspiracy charges on Sept. 17, his legal team proposed a $50 million bond package that included equity in his Miami home and his mother's house, as well as limited his travel to within certain parts of Florida, New York and New Jersey.

The defense also offered, per a letter obtained by E! News, to "walk the Court through a series of actions taken by Mr. Combs over the past six months that prove that he is not a risk of flight or a danger to anyone in the community."

U.S. Magistrate Judge Robyn F. Tarnofsky rejected the package and ordered that Combs be remanded without bail. He remains in custody at the Metropolitan Detention Center in Brooklyn.

"He is not a perfect person," Combs' attorney Marc Agnifilo told the court, per NBC New York. "There has been drug use. He has been in toxic relationships."

Therefore, he added, his client was getting "treatment and therapy for things that he needs treatment and therapy for."

Overall, though, Combs' "spirits are good," the lawyer told reporters after court Sept. 17. "He's confident."

More than 1,000 bottles of baby oil and personal lubricant were seized during the March 2024 raids on Combs' L.A. and Miami homes, according to the 14-page indictment unsealed Sept. 17.

Per the indictment, the oil and lube were stockpiled for use in so-called "freak-offs," the term Combs used for gatherings in which he allegedly orchestrated sexual encounters between women he coerced and threatened into doing his bidding and male sex workers.

"I don't know where the number 1,000 came," his attorney Agnifilo said in the TMZ documentary The Downfall of Diddy: The Indictment, which premiered Sept. 27. Pondering out loud why anyone would need so much, the lawyer added, "He has a big house, he buys in bulk. I think they have Costcos in every place where he has a home."

Costco, meanwhile, wanted no part of it, telling TMZ in a statement that "none" of its U.S. stores carry baby oil.

In May 2024, CNN published a clip of hotel surveillance video from 2016 that appeared to show Combs attacking his then-girlfriend Cassie, born Cassandra Ventura. (The assault matched up with an alleged incident detailed in the lawsuit she filed against Combs on Nov. 16, 2023; both parties announced a settlement the next day.)

"I was f--ked up. I hit rock bottom," Combs said in a video posted to Instagram in response to the footage. "But I make no excuses. My behavior on that video is inexcusable. I take full responsibility for my actions in that video." He had gone to therapy and rehab since, he added, and was "committed to be a better man each and every day."

During a Sept. 18 hearing on Combs' second request for bail, Assistant U.S. Attorney Emily Johnson said, per NBC News, that Combs allegedly sent a text in the days following the assault that read, "Call me, the cops are here." Another read, "I have six kids. Call, I’m surrounded."

Johnson did not say Cassie's name in court. She said that Combs' victim replied via text, "Sick you think it’s OK to do what you've done."

Bail was once again denied, this time by U.S. District Judge Andrew L. Carter Jr.

On Oct. 3, the Combs case was reassigned to Judge Arun Subramanian because Carter was unable to accommodate a trial date.

During an Oct. 10 status hearing, Subramanian set a trial date of May 5, 2025.

Prosecutor Johnson told the judge she expected the trial to last roughly three weeks, but said there was still the possibility that a superseding indictment could lead to more charges against Combs.

Agnifilo said in court they'd need about a week to put on their case.

Meanwhile, the attorney said in the TMZ doc that Combs was looking forward to testifying in his own defense.

“I don’t know that I could keep him off the stand," Agnifilo said. "I think he is very eager to tell his story."