Are there any Diddy moments that aged well? 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.
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00:00What's one misconception about you?
00:01There are no misconceptions about me.
00:04Welcome to WatchMojo, and today we're looking at moments involving Sean P. Diddy combs that
00:09feel disturbing in the wake of his 2024 arrest and indictment, among other things.
00:14If you don't have what they need, they're gonna leave.
00:16Right.
00:16Gotta keep them there.
00:17Right.
00:18Need locks on the doors.
00:21Okay, this is sounding kind of dangerous now.
00:23Diddy parties.
00:25Over the years, numerous celebrities have praised Diddy parties,
00:28from LeBron James to Ben Stiller in the Bad Boys for Life music video.
00:32Listen, uh, if you're having one of your crazy, uh, house party things, shout me a holler, dumb.
00:40In a 2005 VMAs ad, Derek Jeter, Nicole Richie, the Ying Yang Twins, and Fat Joe
00:46reflected on their experiences at Diddy parties, portraying them as can't-miss events.
00:51Given the recent descriptions of Combs' alleged freak-off parties,
00:54these celebrity testimonies come across as insensitive in retrospect.
00:58It's hard to say which is more off the hook, a Diddy party or a Diddy after party,
01:04or a Diddy after after party, which is basically a pre-party for the next Diddy party.
01:12Combs' accounts of his parties have not aged well either.
01:15In a resurfaced video, Combs films a seemingly passed-out DJ named
01:19James as another guest places a drink on his head.
01:22Whether joking or not, Combs claimed that he puts white guys to sleep at his parties
01:27has taken on a more alarming meaning.
01:29For all those in London that don't know what happens to the white man
01:34when he comes to a P. Diddy party, this is what happens to the white man.
01:38Okay, what happens?
01:39Uh, it's so unfortunate.
01:41Usher sees, quote,
01:42"...very curious things."
01:44Usher lived with Combs for about a year during his early teens.
01:47And I lived with Sean Puffy Combs for a year.
01:50That's the crazy thing. Now that was L.A. Reid's idea, right?
01:52In a 2016 appearance on The Howard Stern Show,
01:55Usher recounted his time in New York with Combs.
01:58Usher recalled several names like Biggie Smalls
02:00and Lil' Kim dropping by his parties raged into the early morning.
02:03I went there to see the lifestyle.
02:05Right.
02:05And I saw it.
02:07But I don't know if I could indulge and understand what I was even looking at.
02:11It was pretty wild.
02:12While Usher claims he stayed up later than Combs and his crew,
02:15he wasn't sure if he could, quote,
02:17"...indulge in some of the activities taking place."
02:20Although Usher didn't entirely understand everything going on,
02:23Combs' lifestyle was clearly, quote,
02:26"...wild," quote,
02:27"...crazy," and, quote,
02:28"...curious."
02:29When asked if he would ever send his kids to, quote,
02:32"...Puffy Camp," Usher gave a firm no.
02:34You're a dad now. Would you ever send your kid to Puffy Camp?
02:38Hell no.
02:39Usher said this with a laugh,
02:40but the allegations that have come out since have piqued our curiosity.
02:44Get Him to the Greek
02:46As funny as this 2010 comedy was upon release,
02:49it's hard to rewatch without thinking about how problematic
02:52several cast members have become.
02:54It's better. It's better that you've apologized,
02:56because now we can start to rebuild.
02:58In 2023, two women, one being his ex-girlfriend,
03:02accused Jonah Hill of abusive behavior.
03:05The same year, Russell Brand's history of sexual assault accusations caught up to him.
03:10Then there's Combs, who played hot-headed record producer Sergio Roma.
03:14Oh, y'all think this meeting is for me?
03:16No, no, this meeting is not for me, it's for y'all.
03:19See, I'm gonna be all right. I'm straight.
03:22I got villas in Brazil, Tahiti, East Hampton, West Hampton.
03:26Sergio gonna be fine.
03:27While the character was likely intended as a self-aware send-up
03:31of Combs' bombastic persona,
03:32it might have hit closer to home than the filmmakers realized.
03:36In one notable scene, a whacked-out Sergio goes on a rampage,
03:40chasing Hill and Brand's characters down a hallway.
03:42What are you doing? Run all the way back to L.A.
03:45Nowadays, when we think of Combs running down a hallway,
03:48an infamous video involving Cassie Ventura immediately comes to mind.
03:52Quote,
03:53"'I'm a savage.'"
03:54Combs' YouTube channel posted multiple videos building hype
03:57for the 2017 documentary Can't Stop, Won't Stop.
04:00We want to hit him with that pure, uncut, 1,000% who we are.
04:06If you think that title has taken on an uncomfortable sentiment,
04:09the same can be said about the aforementioned videos.
04:12In one, Combs talks about how important winning is to him,
04:15which has likely never been more true than now.
04:18I want to win over and over and over.
04:20In another clip, Combs sits in his office,
04:23making a deal with MTV over the phone.
04:25Combs is so excited about the outcome that he starts messing up his desk,
04:29proclaiming that he's a, quote,
04:31"'savage' who gets whatever he wants and can't be kept down."
04:35I'm a savage!
04:38I'm a savage!
04:39Taking a breather, Combs proceeds to ask what's next,
04:42although we're not sure he wants the answer.
04:45Jennifer Lopez's Mom
04:47After appearing in the Been Around the World music video,
04:49Jennifer Lopez dated Combs from 1999 to 2001.
04:56In a later interview with Wendy Williams,
04:58the talk show host floated the idea of Lopez and Combs getting back together.
05:02Before Lopez could answer,
05:04she pointed to her mother Guadalupe Rodriguez in the audience.
05:08The horrified expression on Rodriguez's face said everything,
05:12as did a dismissive hand motion.
05:15Look it.
05:16Lopez went on to talk about how Combs sent her 100 white doves,
05:20which wasn't as romantic as he might have envisioned.
05:23Even if this gesture had won Lopez back,
05:26it's safe to say her mother would not have approved.
05:28It's crazy, everybody had, like, everybody came alive.
05:31They all had something to say.
05:32Yeah, everybody has an opinion.
05:33Yes, it's funny to me.
05:35So, but, all right, so no puffy.
05:36Be this due to Combs' suspected infidelity during his relationship with Lopez,
05:40or another reason, Rodriguez has strong parental instincts.
05:44Ashton Kutcher's Hot Ones interview.
05:46Although he has somewhat distanced himself from Combs as of late,
05:50Ashton Kutcher was once proud to call the rapper his friend.
05:53Diddy party stories, they're our favorite genre of anecdote, if you have one, yeah.
05:57Wow, okay, I've got a lot I can't tell.
05:59During his 2019 interview on Hot Ones,
06:02Kutcher was asked if he had any Diddy party stories to share.
06:05Kutcher had plenty, but he struggled to think of one that he could tell.
06:09I can't tell that one either.
06:10I'm, like, actually cycling through them.
06:13With a smile, the actor shifted the subject away from the parties,
06:17instead talking about how he first met Combs and a memorable run the two shared.
06:21While Kutcher avoided discussing any parties,
06:24there has been speculation that he could be called to testify at Combs' trial,
06:28which would put him in a much hotter seat.
06:30In any case, Kutcher's comment that Combs, quote,
06:33can't lose, plays differently now.
06:35Well, he just can't lose.
06:37Even when he's that close to humility, that, like, it becomes a driver,
06:41and so then he went out and ran the New York Marathon.
06:43The world is filled with uncomfortable lyrics.
06:46Combing through Diddy's discography, some of his music sounds almost prognostic.
06:50Yo, the sun don't shine forever, but as long as it's here,
06:54then we might as well shine together.
06:56This includes the music video for 1998's Victory,
06:59in which the artist runs away from the authorities.
07:03Of all the songs he collaborated on,
07:051997's The World Is Filled may be the most unnerving to revisit.
07:09Throughout his verse, Combs sings about how it's a, quote,
07:12privilege for women to be with him,
07:14although the lyrics paint a much more troubling portrait.
07:17Well, won't you admit it?
07:18I ain't gotta talk it cause I live it.
07:20Any chick can f*** with me, believe me that's a privilege.
07:23The line, quote,
07:24never give up freedom feels especially ironic and creepy.
07:28This isn't just because Combs has been arrested,
07:30but considering that the charges against him include sex trafficking,
07:34there's more than one way to interpret the word freedom here.
07:37We date him like we hate him, see him like we don't need him,
07:40treat him like we need him, and never give him freedom.
07:43Donald Trump's, quote,
07:44good friend.
07:45The year was 2012.
07:47Combs was making a cameo on It's Always Sunny in Philadelphia,
07:51while a future commander-in-chief was endorsing the rapper
07:54on Celebrity Apprentice 5.
07:55Working for Diddy.
07:57Absolutely.
07:57I love Diddy.
07:58When Aubrey O'Day brought up Combs,
08:00Donald Trump was quick to champion him.
08:02As Trump called Combs a, quote,
08:04good friend,
08:05O'Day wasn't willing to comment on whether she thought he was a, quote,
08:08good guy.
08:09Is he a good guy?
08:11I don't want to answer that question.
08:12Well, I think he's a good guy.
08:13I'm going to stick up for him.
08:14Our perceptions of Trump and Combs have drastically changed
08:18since this episode aired.
08:19Combs has reciprocated Trump's friendship in the past,
08:22although in an interview with Jimmy Kimmel,
08:24the singer said he wouldn't want to run for president like him.
08:27I don't know if I could be responsible for the whole country.
08:30Kimmel thought Combs would be a better leader than Trump,
08:33but the host might just might be reconsidering that statement.
08:37His All That appearance.
08:39The docu-series Quiet on Set shined a spotlight on the dark side of several
08:42Nickelodeon shows such as All That.
08:45I was so excited, but I had no idea what kind of wild ride I was getting into.
08:55In 2002, Combs appeared in the sketch comedy's now infamous Little Fetus episode.
09:00Combs' presence has only added to the notoriety.
09:03The episode contains a few moments that aged like milk,
09:06including young girls cheering for Combs,
09:08and the singer's giant head looking through a young boy's window.
09:21In the cringiest scene,
09:23Jack DeSena and Brian Hearn try to wake up Shane Lyons.
09:26They turn to Diddy, who gives them a toy helicopter
09:29and tells him to shove it down Shane's pants.
09:32When that doesn't work, Combs hands them the remote control,
09:35and the boys turn the helicopter on, awakening Shane to a world of pain.
09:46You know, for kids.
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10:06In 2009, a video was posted to Justin Bieber's YouTube page
10:10featuring the teenage singer and Diddy.
10:18Addressing the camera,
10:19Combs said Bieber would be hanging out with him for 48 hours.
10:22Combs wouldn't divulge exactly what they would be up to,
10:25but he presented it as a dream come true for a boy of Bieber's age.
10:29It seemed innocent, even cool at the time.
10:42Fifteen years later, though,
10:43we can't help but read more into the awkward word choice.
10:47For the record, Combs says,
10:50but it sounds like something else.
10:52The two reunited in another video,
10:54where Combs mentions they haven't seen each other in a while.
10:57This prompts Bieber to give him a fake number.
10:59Okay.
10:59My number?
11:00Yeah, yeah, yeah.
11:00I'm gonna tell you my number.
11:01Yeah, yeah, yeah.
11:02Yeah, yeah.
11:02It's 555.
11:03Yes.
11:04Okay.
11:045555.
11:05Okay, 555.
11:07Y'all heard that?
11:07What Diddy moments do you look at differently?
11:10Let us know in the comments.
11:11Your parents ain't let you watch the Cosby show when you was coming up?
11:14Oh, my parents would never have let me watch something like that.