Summary

  • Diddy's celebrity friendships, including with Justin Bieber and Usher, revealed alarming truths about his behavior.
  • Howard Stern spilled the tea on wild parties at Diddy's house even decades before the rapper's allegations.
  • Diddy's feuds with 50 Cent and Eminem revealed alarming aspects of his personality and past involvement.

Ever since the heinous allegations against famed rapper and entrepreneur, Sean 'P. Diddy' Combs came to light, the music superstar has been on the defensive. He even tried pointing to one of his accuser's criminal pasts to defend himself. However, with the release of surveillance footage of him beating his ex-girlfriend, Casandra Ventura, the disgraced star is facing the ultimate condemnation.

In the past, former employees of Diddy have revealed what he's really like to work for; many of whom corroborated some of the claims against him. But certain stars have been given the public warnings about Diddy for years. This article will reveal which A-list celebrities, both former friends and then enemies of Diddy, tried to alert the public to the man's behavior.

Diddy's Former Celebrity Friends Tried To Warn Everyone About His Bad Behavior

The shocking allegations against P. Diddy followed raids on his house that shocked the majority of his fanbase. However, they may not have been all that surprising to some of the people who were close to him. Among them are Usher and Justin Bieber, both of whom hung out with Diddy at young ages. And both of whom claimed they saw some wild things while hanging out with Diddy.

In 2016, Usher sat down for an interview with Howard Stern who asked the R&B singer about his experience with Diddy. According to indy100, Usher spent a year living with Diddy when he was 13. While staying at Diddy's house, he saw the lifestyle Diddy was engaging in:

"I don't know if I could indulge and understand what I was even looking at. It was pretty wild."

Howard Stern, Usher, and P Diddy
A photo of Howard Stern, Usher, and P Diddy.
via Depositphotos

Stern then asked Usher if he would send his kids to hang out with Diddy to which the singer simply said, "Hell no."

It seems Justin Bieber had similar experiences hanging around Diddy at a young age, albeit in a more indirect way. As of this writing, Bieber hasn't commented on what went down with Diddy. However, The National Post revealed videos of a teenaged Bieber with Diddy that haven't aged well. In the clips, both Diddy and Bieber claimed they were up to things they couldn't discuss on camera.

Justin Bieber, Sean Diddy Combs
Justin Bieber, Sean Diddy Combs
Instar

The details have what's gone down at Diddy's infamous house parties have been discussed by many celebrities before and after his 2024 raid. Even Howard Stern spilled some T about what went down at Diddy's house. While the news of Stern's terrible experience at Diddy's house party came to light after Diddy's allegations were made known, the radio legend actually discussed them on his show almost two decades prior.

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After being interviewed on The Howard Stern Show, Diddy invited Stern and his wife, Beth, to a party at his house. Stern later claimed that he had an awful time due to not being allowed in Diddy's house. He also claimed that the place was crawling with bikini-clad women who he had no idea how Diddy knew.

Diddy's Celebrity Feuds Revealed The Dark Side Of His Behavior

P. Diddy has engaged in some of the music industry's biggest celebrity feuds. While he wasn't always "in the wrong" when it came down to these interactions, they almost certainly revealed aspects of his personality that people now have come to be repulsed by. Perhaps most famous of all is Diddy's ongoing feud with 50 Cent.

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50 Cent has not stopped talking about Diddy during his trial and since the allegations became mainstream. However, 50 (aka Curtis Jackson) has been raising the alarm bells about Diddy for years. Months before the allegations broke, 50 Cent was recorded bashing Diddy's infamous parties at an October 2023 concert.

“[He’ll] hug you from the front and the back at the same time? F–k you talkin’ about? Look, if you into that, you into that. I’m fine with it. To each his own. I’m just sayin’ this ain’t my motherf–king kind of party. It’s uncomfortable. I think I belong in the girls’ bathroom when s–t like that is going on.”

Lil Rod named 50 Cent's ex-girlfriend, Daphne Joy, as one of the women at the center of Diddy's scandal. Joy denied these claims but 50 Cent has publicly tried to get her to come out against his arch-nemesis.

50 Cent and Diddy's feud began in 2006, according to Us Weekly. The "In Da Club" rapper alleged that Diddy knew who took out Notorious B.I.G., insinuating that Diddy was involved with some very bad people. Nowadays, 50 Cent is much more straight up with his feelings about P. Diddy, as he is a vocal supporter of the allegations against him.

50 Cent attends the 2012 American Music Awards
50 Cent attends the 2012 American Music Awards in Los Angeles.
Via: Instar

Of course, 50 Cent isn't the only rapper that Diddy has feuded with. Eminem is also someone who rubbed Diddy the wrong way. And just like 50 Cent, Eminem alleged that Diddy was involved in some violent activities. In fact, Eminem suggested that Diddy knew quite a bit about what happened to Tupac, according to Us Weekly.

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American singer Aubrey O'Day has been making news in the light of Diddy's scandal. In fact, she's been incredibly vocal about her experience working with him. However, O'Day actually revealed some truly disturbing facts about Diddy back in 2019. According to an interview with Variety, O'Day detailed her negative experience with Diddy on the set of 2005's Making The Band, a reality TV show that he oversaw. The interview preceded the allegations against Diddy but even then O'Day claimed that he treated women in problematic ways.

"Diddy's a father, so hopefully he's learned things about the way that you handle women and has more compassion for women now."

Aubrey O'Day, Diddy Combs
Aubrey O'Day, Diddy Combs
Instar

In her interview with Variety, O'Day continued by saying that P. Diddy (also known as Puff Daddy) was "very difficult" to work with as he was a perfectionist. While O'Day was a contestant/personality on the reality show, she found Diddy to be overly critical, including of her appearance. Everything including how her toenails looked was of interest to him.

"We would be in rehearsals performing an hour-and-a-half set over and over and he would walk in for five minutes with a camera and say, 'Aubrey, why are you sweating? You look like a wet dog. You're the hot one, so do you think anyone wants to see that?'"

Diddy on the red carpet
A closeup of Diddy, along with a shot of the rapper in a pink suit.
via Instar

O'Day admitted that she and her fellow co-stars were terrified of Diddy as they experienced his intensity and sexist remarks. O'Day's mother was the one who ultimately told her to "suck it up" and work through it. While O'Day doesn't regret her time on Making The Band, she did warn the world of Diddy years before the mainstream found out what he could be like.

Wendy Williams Slammed P. Diddy For His Treatment Of Cassie Ventura

Casandra Ventura's name is everywhere due to both her lawsuit against former boyfriend P. Diddy but also the recent release of the surveillance footage that showed him beating her. But Wendy Williams sounded the alarm on their relationship years earlier.

 Wendy Williams And P Diddy feud
Sean combs P. Diddy feud with Wendy Williams looking shocked and angry
Via: Instar

Williams and Diddy have had beef ever since the early 1990s when she alleged that he was gay. According to E!, Williams claimed that he got her fired from the radio station she worked at as a result. In 2015, Williams escalated the feud between them when she slammed Diddy for treating Cassie Ventura like "a possession".

Not only did Wendy Williams warn the public of Diddy's bad behavior in regard to how he handles revenge, but she also raised the alarm bells about his treatment of Cassie Ventura years before it went public.