It seems like Pandora’s Box has opened since Sean ‘Diddy’ Combs was arrested at a hotel in New York and later charged with sex trafficking, racketeering, and transportation to engage in prostitution.
The 54-year-old musician is said to be on suicide watch while currently remanded to Brooklyn’s Metropolitan Detention Center after being denied bail twice.
His Los Angeles mansion was raided in March, police reportedly seized supplies intended for use in orgies, including drugs and more than 1,000 bottles of baby oil.
The current court case against him follows a year in which several women filed lawsuits against him, including his ex Cassie, who said he used his authority to orchestrate a ‘manipulative and coercive romantic and sexual relationship.’
By July this year, eight lawsuits had been filed against him. Combs denies the allegations brought against him.
Following his arrest, numerous interview clips and interactions involving the rapper and warnings posed by other celebs have resurfaced shocking the public.
Here, we look at some of the most sinister examples that didn’t quite spark the same backlash when they first occurred.
His uncomfortable relationship with Justin Bieber
A 2002 children’s TV show featuring Combs and pop icon Justin Bieber has caused fans concern.
In an appearance on Dan Schneider’s Nickelodeon show All That, Combs tells two children to put a toy down a sleeping boy’s trousers, raising eyebrows online.
But this isn’t all, with a resurfaced video of Diddy with 15-year-old Bieber seeing him tell the camera that he’s been given ‘custody’ of Bieber for ’48 hours.’
The clip begins with Combs showing Bieber his sports car and promising him he can drive the vehicle once he turns 16.
‘You ever seen the movie 48 Hrs? Right now [Justin is] having 48 hours with Diddy, him and his boy,’ the rapper tells the camera.
‘They’re having the times of their lives, like where we hanging out and what we’re doing we can’t really disclose. But it’s definitely a 15-year-old’s dream.’
He continues, ‘I have been given custody of him. You know, he’s signed to Usher and I had legal guardianship of Usher when he did his first album. I did Usher’s first album.’
Combs then asks Bieber what he wants to do, to which Bieber responds, ‘Let’s go get some girls.’
‘Man after my heart,’ the rapper responds. ‘That’s what I’m talking about.’
Another clip, taken in 2010 when Bieber was 16, shows the young singer stuttering and looking uncomfortable as Combs asks him why he doesn’t hang out with him anymore.
In a 2023 titled ‘Justin Bieber’s Mom Speaks out: Usher & Diddy’s Impact on His Life Exposed,’ Bieber’s mother claims that the rapper offered Bieber cocaine, marijuana, and alcohol at his parties. She goes on to say that she was forced to intervene to protect her son.
Strange footage from 2021 of Combs and Bieber shows the Last Night artist patting his fingers on Bieber’s chest while his other hand rests on his upper arm.
Then Combs slaps the other side of Justin’s chest before going in for a hug and whispering something to him, though what he says is unclear.
Talking about ‘locking women up at parties’ on TV
A resurfaced interview from 22 years ago sees Combs make shocking claims about women.
The now-viral interview, which originally aired in 2002 on Late Night With Conan O’Brien, featured Combs making unsettling jokes about keeping women from leaving his parties.
The resurfaced interview shows the music mogul, once considered one of the industry’s most powerful figures, giving Conan O’Brien advice on how to throw a ‘killer party.’
While initially offering light-hearted tips – such as ensuring there were ‘beautiful women’ and ‘beautiful men for the ladies’ along with ‘alcohol’ and water – Combs then made a disturbing comment about keeping women from leaving the party.
‘If you don’t have what they need, they’re gonna leave,’ Combs said, referring to water at parties. ‘You need locks on the doors.’
O’Brien, taken aback by the remark, paused before responding, ‘Okay, this is sounding kind of dangerous now.’
Combs, seemingly unfazed, replied, ‘It’s a little kinky,’ and continued offering party tips.
He went on to suggest turning off the air conditioning at parties, claiming that heat affects how alcohol is consumed and makes people ‘a little more comfortable and loose.’
O’Brien attempted to inject some humour into the uncomfortable moment by responding, ‘That just sounds disgusting.’
Mike Tyson moved the rapper’s hand away from him
Boxing legend Mike Tyson took part in an awkward interview with Combs in 1998 which has since gone viral.
The stars appeared on an episode of the Keenan Ivory Wayans Show, with both of them sitting next to each other on the sofa.
While speaking to host Keenan Ivory Wayans, Tyson holds Combs’ hand up to show the host a ring.
He then moves the hand, which had been placed close to Tyson’s leg, onto Combs’ own leg before moving forward on the sofa.
Travis Scott running away from him
Another awkward encounter between Combs and Travis Scott was captured on camera and has been shared across social media.
In a video of Travis and Combs, the latter says to the camera: ‘Me and my baby bro, we’re here, tomorrow it’s time… what you gonna do to that thing man?’
Scott backs away from Combs, visibly uncomfortable, before he runs away screaming loudly and seemingly telling Combs to ‘shush’.
The clip sees Travis avoid eye contact with Combs, with fans speculating whether or not they are speaking in code words.
Khloe Kardashian claimed people were ‘butt naked’ at a Diddy party
In an unearthed clip from Keeping Up With The Kardashians, Khloe Kardashian recalls what she witnessed at one of Combs’ parties.
In the 2014 episode titled Secrets of A Double Life, she tells sister Kourtney: ‘I got on a plane at 5.30am. Well this party…I think half the people there were butt-naked. You would have loved it.’
Kourtney then asks Khloe who she was with at the party, to which she replies: ‘A bunch of my friends’ naming Combs, Quincy Brown, Justin Bieber, and French Montana.
An interview between Combs, Kourtney and Khloe in 2016 on the Kocktails with Khloe talk show saw the trio discuss one of his parties.
Khloe claimed: ‘I know you’re known for the parties. When you think of a party or a good time, you think of Puff.’
She and Kourtney then recalled attending one of Combs’ birthday parties, with Kourtney saying: ‘That night was fun ’cause all the girls ditched me, so I was like me and the boys. Like it was me, Kanye [West], Corey [Gamble], T [Tyga] and we were all just like hanging out and it was fun.’
Ashton Kutcher has a ‘lot he can’t tell’ about Diddy parties
An interview Ashton Kutcher gave in 2019 has emerged online, in which he opened up about his close friendship with the disgraced rapper.
While appearing on Hot Ones, host Sean Evans asked Kutcher for an ‘anecdote’ from Combs’ party days.
‘Diddy party stories, they’re our favourite genre of anecdote if you have one,’ Evans asked.
‘I’ve got a lot I can’t tell,’ Kutcher replied. ‘Can’t tell that one either…I’m actually cycling through them. Diddy party stories… man, that was some weird memory lane thing.’
‘Our relationship is really bizarre,’ he continued. ‘It started over Punk’d because he was like, “Yo, you can’t punk me!” I was like, “I don’t know what to tell you, everybody is on the table.”
‘That started our conversation. We became fast friends and we used to just hang out, and watch football together.’
Jennifer Lopez’s mum’s reaction to a possible reunion
A resurfaced photo of Combs alongside his ex Jennifer Lopez and R&B star Aaliyah has gone viral following his arrest.
The image from 2000 at the rapper’s Fourth of July party shows a group of people lying in bed, including Combs, Lopez, Aaliyah, Andre Harrell, Natane Adcock, and Damon Dash.
J-Lo and Combs were in a relationship, which lasted from 1999 to 2001.
A resurfaced clip from 2015 seems to show Lopez’s mother’s disdain for the rapper after it was suggested J-Lo and Combs could get back together.
During an appearance on The Wendy Williams Show, host Williams says: ‘I could always see you getting back with Puffy in a little way.’
J-Lo then points out her mother, Guadalupe Rodríguez, in the audience, who simply says ‘It’s done’ with a clearly disapproving expression.
Kanye West makes shocking claims against the rapper
Controversial rapper Kanye West made shocking claims about Combs in 2022.
The Gold Digger rapper alleges that some celebrities make deals with law enforcement to keep them out of prison.
He accuses Combs of being a ‘fed’, telling the Drink Champs podcast: ‘The reason why you gotta talk is because you did a deal, you f*****g fed!
‘That’s why you’ve gotta come at me, because part of the deal for you to be able to do all that and get out of jail is that you promised that you are gonna go pull my card.’
Combs has not publicly addressed West’s claims.
Tupac’s warning about Diddy
Tupac Shakur made a chilling claim about Combs shortly before his death in 1996.
The Hit Em Up rapper was shot five times on November 30, 1994, during a robbery at New York’s Quad Studios.
When speaking about the incident in 1995 with Vibe magazine, Tupac said he believed Combs was involved in the shooting.
‘I believe so, I do believe so,’ he said. ‘I have proved things that I can say that will back up my claim’ but that it was not for the world to know about.
‘It’s between me and him, and only he knows.’
An LAPD officer made a sensational claim that Combs hired men to kill Tupac, which Combs had denied.
Audio from one of his parties leaves him speechless
Combs was left speechless when audio from one of his parties in Miami was broadcast on a radio show.
During a 2018 episode of Charlamagne Tha God’s radio show The Breakfast Club, he joked with Combs about him being drunk at a party.
They played audio from the event, where Combs could be heard saying: ‘I like it when you like this daddy, daddy I like the way you’re scrambling and scraping for s**t.’
Combs appeared shocked, simply responding with ‘hey… man’ while not denying it was him on the recording.