10 Most Disturbing Diddy Moments Because of What We Know Now

10 Most Disturbing Diddy Moments Because of What We Know Now

Welcome to WatchMojo, and today we’re looking at moments involving Sean ‘P. Diddy’ Combs that feel disturbing in the wake of his 2024 arrest and indictment, among other things.

Diddy Parties

Over the years, numerous celebrities have praised “Diddy parties,” from LeBron James to Ben Stiller in the “Bad Boys for Life” music video. In a 2005 VMAs ad, Derek Jeter, Nicole Richie, the Ying Yang Twins, and Fat Joe reflected on their experiences at Diddy parties, portraying them as can’t-miss events. Given the recent descriptions of Combs’ alleged “freak off” parties, these celebrity testimonies come across as tone-deaf in retrospect. Combs’ accounts of his parties haven’t aged well either. In a resurfaced video, Combs films a seemingly passed-out DJ named James as another guest places a drink on his head. Whether joking or not, Combs’ claim that he puts white guys to sleep at his parties has taken on a more alarming meaning.

Usher Sees “Very Curious Things”

Usher lived with Combs for about a year during his early teens. In a 2016 appearance on “The Howard Stern Show,” Usher recounted his time in New York with Combs. Usher recalled names like Biggie Smalls and Lil' Kim dropping by as parties raged into the early morning. While Usher claims he stayed up later than Combs and his crew, he wasn’t sure if he could “indulge” in some of the activities taking place. Although Usher didn’t entirely understand everything going on, Combs’ lifestyle was clearly “wild,” “crazy,” and “curious.” When asked if he would ever send his kids to “Puffy camp,” Usher gave a firm “no.” Usher said this with a laugh, but the allegations that’ve come out since have piqued our curiosity.

“Get Him to the Greek” (2010)

As funny as this 2010 comedy was upon release, it’s hard to rewatch without thinking about how problematic several cast members have become. In 2023, two women, one being his ex-girlfriend, accused Jonah Hill of abusive behavior. The same year, Russell Brand’s history of sexual assault accusations caught up to him. Then there’s Combs, who played hotheaded record producer Sergio Roma. While the character was likely intended as a self-aware send-up of Combs’ bombastic persona, it might’ve hit closer to home than the filmmakers realized. In one notable scene, a whacked-out Sergio goes on a rampage, chasing Hill and Brand’s characters down a hallway. Nowadays when we think of Combs running down a hall, an infamous video involving Cassie Ventura immediately comes to mind.

“I’m a Savage”

Combs’ YouTube channel posted multiple videos building hype for the 2017 documentary, “Can’t Stop, Won’t Stop.” If you think that title has taken on an uncomfortable sentiment, the same can be said about the aforementioned videos. In one, Combs talks about how important winning is to him, which has likely never been more true than now. In another clip, Combs sits in his office, making a deal with MTV over the phone. Combs is so excited about the outcome that he starts messing up his desk, proclaiming that he’s a “savage” who gets whatever he wants and can’t be kept down. Taking a breather, Combs proceeds to ask what’s next, although we’re not sure he wants the answer.

Jennifer Lopez’s Mom

After appearing in the “Been Around the World” music video, Jennifer Lopez dated Combs from 1999 to 2001. In a later interview with Wendy Williams, the talk show host floated the idea of Lopez and Combs getting back together. Before Lopez could answer, she pointed to her mother Guadalupe Rodriguez in the audience. The horrified expression on Rodriguez’s face said everything, as did a dismissive hand motion. Lopez went on to talk about how Combs sent her 100 white doves, which wasn’t as romantic as he might’ve envisioned. Even if this gesture had won Lopez back, it’s safe to say her mother wouldn’t have approved. Be this due to Combs’ suspected infidelity during his relationship with Lopez or another reason, Rodriguez has strong parental instincts.

Ashton Kutcher’s “Hot Ones” Interview

Although he’s somewhat distanced himself from Combs as of late, Ashton Kutcher was once proud to call the rapper his friend. During his 2019 interview on “Hot Ones,” Kutcher was asked if he had any Diddy party stories to share. Kutcher had plenty, but he struggled to think of one that he could tell. With a smile, the actor shifted the subject away from the parties, instead talking about how he first met Combs and a memorable run the two shared. While Kutcher avoided discussing any parties, there’s been speculation that he could be called to testify at Combs’ trial, which would put him in a much hotter seat. In any case, Kutcher’s comment that Combs “can’t lose” plays differently now.

“The World Is Filled…” With Uncomfortable Lyrics

Combing through Diddy’s discography, some of his music sounds almost prognostic. This includes the music video for 1998’s “Victory,” in which the artist runs away from the authorities. Of all the songs he collaborated on, 1997’s “The World Is Filled…” may be the most unnerving to revisit. Throughout his verse, Combs sings about how it’s a “privilege” for women to be with him, although the lyrics paint a more troubling portrait. The line, “Never give up freedom,” feels especially ironic and creepy. This isn’t just because Combs has been arrested, but considering that the charges against him include sex trafficking, there’s more than one way to interpret the word “freedom” here.

Donald Trump’s “Good Friend”

The year was 2012. Combs was making a cameo on “It’s Always Sunny in Philadelphia” while a future Commander in Chief was endorsing the rapper on “Celebrity Apprentice 5.” When Aubrey O’Day brought up Combs, Donald Trump was quick to champion him. As Trump called Combs a “good friend,” O’Day wasn’t willing to comment on whether she thought he was a “good guy.” Our perceptions of Trump and Combs have drastically changed since this episode aired. Combs has reciprocated Trump’s friendship in the past, although in an interview with Jimmy Kimmel, the singer said he wouldn’t want to run for president like him. Kimmel thought Combs would be a better leader than Trump, but the host might (just might) be reconsidering that statement.

His “All That” Appearance

The docuseries “Quiet on Set” shined a spotlight on the dark side of several Nickelodeon shows, such as “All That.” In 2002, Combs appeared in the sketch comedy’s now-infamous “Lil' Fetus” episode. Combs’ presence has only added to the notoriety. The episode contains a few moments that aged like milk, including young girls cheering for Combs and the singer’s giant head looking through a young boy’s window. In the cringiest scene, Jack DeSena and Bryan Hearne try to wake up Shane Lyons. They turn to Diddy, who gives them a toy helicopter and tells him to shove it down Shane’s pants. When that doesn’t work, Combs turns the helicopter on, awakening Shane to a world of pain. Ya know, for kids!

Justin Bieber’s 48 Hours with Diddy

In 2009, a video was posted to Justin Bieber’s YouTube page featuring the teenage singer and Diddy. Addressing the camera, Combs said Bieber would be hanging out with him for 48 hours. Combs wouldn’t divulge exactly what they’d be up to, but he presented it as a dream come true for a boy of Bieber’s age. It seemed innocent, even cool, at the time. 15 years later, though, we can’t help but read more into the awkward word choice. For the record, Combs says, “buck full crazy,” but it sounds like something else. The two reunited in another video where Combs mentions that they haven’t seen each other in a while. This prompts Bieber to give him a fake number. We can only speculate why.

What Diddy moments do you look at differently? Let us know in the comments.