- yesterday
Some moments age worse than others.
Welcome to WatchMojo.world where we’re revisiting the 10 most disturbing moments from Sean “Diddy” Combs’ career that feel even more unsettling today. With new information coming to light, these incidents hit very differently in hindsight.
Which moment shocked you the most? Share your thoughts in the comments.
Welcome to WatchMojo.world where we’re revisiting the 10 most disturbing moments from Sean “Diddy” Combs’ career that feel even more unsettling today. With new information coming to light, these incidents hit very differently in hindsight.
Which moment shocked you the most? Share your thoughts in the comments.
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TVTranscript
00:00What's one misconception about you?
00:02There are no misconceptions about me.
00:04Welcome to WatchMojo,
00:05and today we're looking at moments involving Sean P. Diddy Combs
00:08that feel disturbing in the wake of his 2024 arrest and indictment,
00:13among other things.
00:14You know, so if 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.
00:24Diddy 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, if you haven't one of your crazy house party things,
00:37shout me a holla done.
00:40In a 2005 VMAs ad, Derek Jeter, Nicole Richie, the Ying Yang twins,
00:45and Fat Joe reflected on their experiences at Diddy parties,
00:48portraying 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,
01:01a Diddy party or a Diddy after party,
01:04or a Diddy after after party,
01:07which 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,
01:17Combs films a seemingly passed-out DJ named James
01:20as another guest places a drink on his head.
01:22Whether joking or not,
01:24Combs' claim 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
01:32to the white man when he comes to a P. Diddy party,
01:36this is what happens to the white man.
01:38Okay, what happens?
01:38Uh, it's so unfortunate.
01:41Usher sees, quote,
01:42very 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.
01:51Now 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 and Lil' Kim
02:01dropping by as parties raged into the early morning.
02:03I went there to see the lifestyle, and I saw it.
02:07But I don't know if I could indulge and understand
02:10what I was even looking at.
02:11It was pretty wild.
02:12While Usher claims he stayed up later than Combs and his crew,
02:16he wasn't sure if he could, quote,
02:17indulge in some of the activities taking place.
02:20Although Usher didn't entirely understand everything going on,
02:23Combs' lifestyle was clearly, quote,
02:26wild, quote, crazy, and, quote, curious.
02:29When asked if he would ever send his kids to, quote,
02:32Puffy Camp, Usher gave a firm no.
02:35You're a dad now.
02:35Would 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
02:42have 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
02:51how problematic several cast members have become.
02:54It's better.
02:55It's better that you've apologized,
02:56because now we can start to rebuild.
02:58In 2023, two women,
03:00one being his ex-girlfriend,
03:02accused Jonah Hill of abusive behavior.
03:05The same year,
03:06Russell Brand's history of sexual assault accusations
03:08caught up to him.
03:10Then there's Combs,
03:11who 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.
03:18It's for y'all.
03:19See, I'm gonna be all right.
03:21I'm straight.
03:22I got villas in Brazil, Tahiti,
03:24East Hampton, West Hampton.
03:26Sergio gonna be fine.
03:27While the character was likely intended
03:29as a self-aware send-up of Combs' bombastic persona,
03:33it might have hit closer to home
03:34than the filmmakers realized.
03:36In one notable scene,
03:37a whacked-out Sergio goes on a rampage,
03:40chasing Hill and Brand's characters down a hallway.
03:42Where you going?
03:43I'm 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
03:50immediately comes to mind.
03:52Quote,
03:53Combs' YouTube channel posted multiple videos
03:57building hype for the 2017 documentary
03:59Can't Stop Won't Stop.
04:01We want to hit him with that pure,
04:03uncut, 1,000% who we are.
04:06If you think that title has taken on
04:08an 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.
04:21In another clip, Combs sits in his office,
04:23making a deal with MTV over the phone.
04:26Combs is so excited about the outcome
04:28that he starts messing up his desk,
04:30proclaiming that he's a, quote,
04:31savage who gets whatever he wants
04:33and can't be kept down.
04:35Savage! I'm a savage!
04:37Oh! I'm a savage!
04:39Taking a breather,
04:40Combs proceeds to ask what's next,
04:42although we're not sure he wants the answer.
04:45Jennifer Lopez's mom
04:46After appearing in the Been Around the World music video,
04:49Jennifer Lopez dated Combs from 1999 to 2001.
04:53So handsome.
04:55You so well.
04:56In a later interview with Wendy Williams,
04:59the talk show host floated the idea
05:00of Lopez and Combs getting back together.
05:03Before Lopez could answer,
05:04she pointed to her mother,
05:05Guadalupe Rodriguez, in the audience.
05:08The horrified expression on Rodriguez's face said everything,
05:12as did a dismissive hand motion.
05:14Look at that!
05:15Look at that!
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 has, 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
05:38during his relationship with Lopez or another reason,
05:41Rodriguez 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 are our favorite genre of anecdote.
05:56Oh, really?
05:57If you have one, yeah.
05:58Wow, okay, I've got a lot.
05:59I can't tell.
06:00During his 2019 interview on Hot Ones,
06:02Kutcher was asked if he had any Diddy party stories to share.
06:06Kutcher had plenty,
06:06but he struggled to think of one that he could tell.
06:09Can't tell that one either.
06:11I'm, like, actually cycling through them.
06:13With a smile,
06:14the actor shifted the subject away from the parties,
06:17instead talking about how he first met Combs
06:19and a memorable run the two shared.
06:21While Kutcher avoided discussing any parties,
06:24there has been speculation
06:25that he could be called to testify at Combs' trial,
06:28which would put him in a much hotter seat.
06:30In any case,
06:31Kutcher'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,
06:39that, 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,
06:48some of his music sounds almost prognostic.
06:51Yo, the sun don't shine forever,
06:53but as long as it's here,
06:54and we might as well shine together.
06:56This includes the music video for 1998's Victory,
07:00in which the artist runs away from the authorities.
07:03Of all the songs he collaborated on,
07:051997's The World Is Filled
07:07may be the most unnerving to revisit.
07:10Throughout his verse,
07:11Combs sings about how it's a, quote,
07:13privilege for women to be with him,
07:15although the lyrics paint a much more troubling portrait.
07:17Won't you admit it?
07:18I ain't gotta talk it cause I live it.
07:20Any chick 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
07:32include sex trafficking,
07:34there's more than one way to interpret the word freedom here.
07:37We date him like we hate him,
07:39see him like we don't need him,
07:40treat him like we meet him,
07:42and never give him freedom.
07:43Donald Trump's, quote,
07:44good friend.
07:45The year was 2012.
07:47Combs was making a cameo on
07:49It's Always Sunny in Philadelphia,
07:51while a future commander-in-chief
07:53was endorsing the rapper on Celebrity Apprentice 5.
07:56Working 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.
08:12Oh, wow.
08:12I think he's a good guy.
08:13I'm going to stick up for him.
08:14Our perceptions of Trump and Combs
08:16have drastically changed since 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,
08:34just might be reconsidering that statement.
08:37His All That appearance.
08:39The docuseries Quiet on Set shined a spotlight
08:41on the dark side of several Nickelodeon shows,
08:44such as All That.
08:45I was so excited,
08:46but I had no idea
08:49what kind of wild ride
08:52I was getting into.
08:55In 2002,
08:56Combs appeared in the sketch comedy's
08:58now infamous Lil 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.
09:11Good morning.
09:13Just seeing your room.
09:17Hey, hey, hey, hey, hey, stop screaming.
09:20Hey, it's just me, P. Diddy.
09:21In the cringiest scene,
09:23Jack DeSena and Brian Hearn try to wake up Shane Lyons.
09:26They turn to Diddy,
09:27who gives them a toy helicopter
09:29and tells him to shove it down Shane's pants.
09:32When that doesn't work,
09:33Combs hands them the remote control
09:34and the boys turn the helicopter on,
09:37awakening Shane to a world of pain.
09:39Shall I?
09:40By all means.
09:41You know, for kids.
09:48Before we continue,
09:49be sure to subscribe to our channel
09:51and ring the bell to get notified about our latest videos.
09:54You have the option to be notified
09:55for occasional videos or all of them.
09:58If you're on your phone,
09:59make sure you go into your settings
10:00and switch on notifications.
10:04Justin Bieber's 48 hours with Diddy.
10:06In 2009, a video was posted to Justin Bieber's YouTube page
10:10featuring the teenage singer and Diddy.
10:12As soon as you turn 16,
10:15you know what I'm saying?
10:15I'm gonna let you rock
10:16because every time you do that, I'm like, yeah.
10:18Addressing the camera,
10:19Combs said Bieber would be hanging out with him for 48 hours.
10:23Combs 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.
10:32I don't really, I don't have legal guardianship of him,
10:34but for the next 48 hours, he's with me.
10:37So, um, and we gonna go full, buck-full crazy.
10:4215 years later, though,
10:44we can't help but read more into the awkward word choice.
10:47For the record, Combs says, quote,
10:49buck-full crazy, but 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.
10:59My number?
11:00Yeah, yeah, yeah.
11:01I'm gonna tell you my number.
11:01Yeah, yeah, yeah.
11:02It's 555?
11:03Yes.
11:04Okay.
11:045555.
11:06Okay, 55.
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
11:13when he was coming up?
11:14Oh, my parents would never have let me
11:16watch something like that.
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