- 4 months ago
In light of recent allegations, Sean "Diddy" Combs' past public moments take on disturbing new meaning. From his eerie "last words" joke on Martha & Snoop's show to uncomfortable celebrity interactions and questionable party comments, these once-innocuous moments now appear sinister. Join us as we examine Diddy's history through a new lens - revealing red flags hidden in plain sight all along.
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00:00-"Savage! I'm a savage!"
00:02Welcome to WatchMojo, and today we're looking at moments featuring Sean Diddy Combs that have
00:06taken on a chilling new tone in light of 21st-century allegations,
00:10lawsuits, and investigations against the disgraced music mogul.
00:14-"I don't know what you're talking about."
00:18Diddy's last words
00:19Talk about a shocking choice of words. When Sean Diddy Combs appeared on Martha
00:23and Snoop's Potluck Dinner, the rapper was playfully asked what he wanted his final words to be.
00:28His response? Are you ready for this?
00:30-"When I die, I want my last words to be...I did it."
00:34Everyone laughed at the time, assuming it was just Diddy playing up his bad boy persona.
00:38But in the context of the explosive allegations in the 2020s,
00:42the statement feels jarringly ominous. With the soundbite resurfacing,
00:46many now say it sounds more like a confession than a harmless quip.
00:50Sometimes, the most unsettling things are said when the cameras are rolling.
00:54-"We all want to know that, Mark."
00:55Khloe Kardashian's Diddy party revelation. In an episode of Keeping Up with the Kardashians,
01:00Khloe Kardashian chatted about attending one of Diddy's infamous parties alongside a
01:04crowd of other high-profile celebrities.
01:06-"So who was with you this weekend?"
01:08-"A bunch of my friends."
01:11Diddy, Quincy, Justin Bieber.
01:14-"So far, so good."
01:16-"French Montana."
01:17-"I wish we could know half the people you're naming."
01:20What stood out most was her casual revelation that, quote,
01:23everyone was naked. -"Love this party? I think half the people there were butt naked.
01:28You would have loved it."
01:29Okay, so naked party-goers at a celebrity bash might seem like typical Hollywood excess.
01:34But paired with new information about what allegedly happened at some of Diddy's events,
01:39it becomes harder to laugh off.
01:40-"Another woman is accusing Sean Diddy Combs of sexual assault in a lawsuit."
01:45Khloe's comment now points to an alleged environment of unchecked
01:48debauchery that may have included manipulation, coercion, or worse.
01:53Wanting to party with the princes
01:54-"Just go over for some tea or something, and we can kick it."
01:57Diddy's parties and their guest list have long captivated the public,
02:01and British talk show host Graham Norton was no exception.
02:04In a 2011 interview, Norton brought up a rumor that Diddy had once tried to invite
02:08Princes William and Harry to one of his soirees.
02:10-"Not anymore. I mean, before, you know."
02:12-"Don't ruin our royal wedding for us."
02:18-"Trust me, they're off the list."
02:19Diddy went on to talk about wanting to party with the princes when they were, quote,
02:22young bucks, and implied they would be interested because of their reputation for mischief.
02:27-"Before, when they were young bucks growing up,
02:29and they were getting in a lot of trouble themselves, so hey, I was like,
02:32why don't you come hang out with me?"
02:33In hindsight, some are questioning why a grown man in his 40s would have been so fixated
02:38on partying with two young men. With the accusations in the 2025 criminal trial,
02:42having involved vulnerable individuals, the moment doesn't read quite as innocently anymore.
02:47-"Sean Diddy Combs, a music mogul, is facing a series of new civil lawsuits,
02:51including allegations he sexually assaulted two teenagers."
02:55After after-parties with Ellen DeGeneres.
02:58-"Hello, Diddy Puppy Daddy Combs.
03:02Love."
03:02Looking at past interactions between Sean Diddy Combs and Ellen DeGeneres is quite eye-opening.
03:07Combs made multiple appearances on Ellen's show, where his infamous parties were a frequent topic
03:12of lighthearted banter. At one point, Ellen even extended an invitation for him to attend one of
03:17her own.
03:18-"Are you going to be early for my party?"
03:19-"Yes, I am. No."
03:21-"No."
03:22-"You know I have to arrive fashionably late."
03:24However, during a particular appearance, Diddy brought up his legendary after-after parties.
03:29Ellen's response?
03:30That would be a curious...
03:31-"No, I know about them."
03:35Of course, these parties ultimately became a focal
03:38point in allegations against the rapper, and the clip is now scrutinized not for what was said,
03:42but for what wasn't.
03:44-"And then, you know, we have the top two floors."
03:46The Cheesecake Walk
03:47-"I want me a piece of cheesecake."
03:49Making the Band was a reality TV series that followed Sean Diddy Combs as he searched for and
03:54developed The Next Big Music Group. But on an episode of Making the Band 2, Diddy ordered aspiring
03:59singers to walk from Midtown Manhattan to Brooklyn just to fetch a slice of cheesecake.
04:04-"I gotta get up every day and do a bunch of s*** that I don't want to do."
04:07-"I gotta bite my tongue and I gotta do it with a smile on my face."
04:12-"But I do want some cheesecake."
04:14While reality TV often blurs the line between entertainment and exploitation,
04:18Diddy's humiliating demand was so excessive it sparked backlash, even back then.
04:23Today, the 12-mile round trip is viewed as a disturbing display of power and psychological
04:28manipulation. The moment has become symbolic of how Diddy allegedly pushes people to uncomfortable
04:33extremes.
04:34-"And you looking at me in my face telling me,
04:36you ain't gonna do something. I can see if I told you to go rob a bank, you know what I'm saying?"
04:40Commenting on Wendy Williams' teenage son.
04:42-"Got a lot to talk about."
04:44To say Wendy Williams and Diddy have had a rocky history would be an understatement. Still,
04:49they managed to set aside their differences for various interviews over the years.
04:52-"You are exhausting me. Let me tell you something. This week has been hella exhausting."
04:57However, in 2017, things got awkward on Wendy's talk show when the conversation turned to her then 16-year-old
05:04Williams' son, Kevin Hunter Jr. While promoting Can't Stop Won't Stop, Diddy stressed that the film
05:08wasn't about money, but about uplifting Black men and women. As the audience applauded, Williams brought
05:14up her son, prompting Diddy to say he'd met Kevin backstage and called him, quote,
05:18"...a great young man."
05:19-"As the mother of a now 16-year-old."
05:22-"Who I met backstage who is..."
05:24-"He did?"
05:25-"He's a great, great young man."
05:26-"Oh, thank you."
05:27Williams' uneasy reaction was hard to miss, and in light of allegations of inappropriate
05:32interest in younger individuals, the moment now feels far more unsettling.
05:36Party permits and premonitions
05:38In the late 90s, Sean Diddy Combs reigned as the so-called king of the party scene,
05:43and that's exactly what he was treated as in a 1999 interview with Entertainment Tonight.
05:48-"Your parties are the hottest ticket in town. People dying to get into your party. How does that
05:53make you feel?"
05:54-"I mean, it's cool."
05:55Of course, in hindsight, that glowing portrayal as the ultimate host likely feels regrettable.
06:00-"Your parties are the hottest ticket around."
06:03-"They won't even give me a permit for the parties, man."
06:06During the interview, Diddy casually admitted that he often threw parties without permits,
06:10and joked that one day he might be arrested for just trying to, quote,
06:14"...have a good time."
06:15-"You're gonna hear about my parties. They're gonna be shutting them down.
06:17They're gonna probably be arresting me, doing all types of crazy things,
06:20just because we want to have a good time, you know."
06:23More than 25 years later, those remarks now sound eerily like foreshadowing,
06:27considering the serious allegations, many tied to those very parties that have surfaced.
06:32Mike Tyson redirects Diddy's hands.
06:34While appearing on the Keenan Ivory Wayans show alongside Mike Tyson,
06:37Diddy appears to get a little handsy with the boxing legend.
06:41You see, in a resurfaced clip, Tyson can be seen firmly grabbing and redirecting Diddy's
06:46hands away from his derriere during a group chat on the couch.
06:49-"It truly is about the Benjamin, as we see."
06:51-"Oh, yes, he's glittering."
06:55People joked that Diddy was just being extra touchy, but with serious allegations about abuse
07:00involving men and women, this clip may prove as an early example of improper behavior,
07:04showing that he made people uneasy long before the headlines. Tyson's nonverbal response is clear.
07:10Boundaries were crossed. And when Iron Mike shuts you down, you know it's serious.
07:15Travis Scott runs from Diddy
07:17Talk about a fight-or-flight response. A resurfaced video of Diddy and Travis Scott
07:22captures Diddy draping his arm around the wrapper and calling him his, quote,
07:25"...baby bro."
07:26-"You ready?"
07:27-"Yeah."
07:28-"Ayo, everybody, my baby bro, we here?"
07:32The mood quickly shifts as Travis looks visibly uncomfortable,
07:35dodges eye contact, shushes Diddy, and abruptly bolts off, yelling as he flees.
07:40-"They better tune in! They better tune in! Let's go!"
07:45Social media speculated, but at the time, it felt like a random moment of silly awkwardness.
07:50Fast forward to today, and Travis's body language is being viewed through an entirely different lens.
07:56Given the nature of the accusations Diddy faced in his 2025 criminal trial,
08:00Scott's instinctive avoidance feels eerily prescient.
08:03-"Tune in! Let's go!"
08:06Locks on the doors.
08:07-"You're legendary for the parties that you throw.
08:09You throw a great party."
08:11-"I'm a legend, baby, for a whole bunch of things."
08:13Conan O'Brien has interviewed his share of celebrities who later made headlines for all
08:16the wrong reasons. Take convicted actor Danny Masterson, for example.
08:20-"Um, I've heard about you. Uh, and you'll be caught soon. I know you will."
08:24Back in 2002, Sean Diddy Combs joined Conan for what seemed like a lighthearted chat.
08:29When asked about the secret to hosting a legendary puffy party,
08:32Diddy rattled off the usual suspects like beautiful women and booze, but then added, quote,
08:37locks on the doors. -"You need locks on the doors?
08:42Okay, this is sounding kind of dangerous now."
08:44At the time, it came off as a cheeky quip, but in light of the accusations that Diddy faced in 2025,
08:50which were centered around his infamous parties, that comment, and the entire exchange,
08:54feels a lot more disturbing. -"Everybody gets a little bit more comfortable and loose.
08:58Pills up a nice little sweat.
09:00That just sounds disgusting. It depends on the way you look at it."
09:05Conan's trademark curiosity may be something he now wishes he'd steered elsewhere.
09:09Speaking of Diddy's bashes, Diddy parties.
09:13Over the years, numerous celebrities have praised Diddy parties, from LeBron James to Ben Stiller
09:18in the Bad Boys for Life music video.
09:20-"Listen, if you're having one of your crazy house party things, shout me a holla dunk."
09:28In a 2005 VMAs ad, Derek Jeter, Nicole Richie, the Ying Yang twins, and Fat Joe
09:34reflected on their experiences at Diddy parties, portraying them as can't-miss events.
09:38Given the description in the 2020s of Combs' alleged freak-off parties,
09:43these celebrity testimonies come across as insensitive in retrospect.
09:47-"It's hard to say which is more off the hook, a Diddy party or a Diddy after party,
09:53or a Diddy after after party, which is basically a pre-party for the next Diddy party."
10:00Combs' accounts of his parties have not aged well either. In a resurfaced video,
10:05Combs films a seemingly passed-out DJ named James as another guest places a drink on his head.
10:11Whether joking or not, Combs' claim that he puts white guys to sleep at his parties
10:15has taken on a more alarming meaning.
10:17-"For all those in London that don't know what happens to the white man when he comes to a P. Diddy party,
10:24this is what happens to the white man."
10:26-"Okay, what happens?"
10:28-"Uh, it's so unfortunate."
10:29Usher sees, quote,
10:31"...very curious things."
10:32Usher lived with Combs for about a year during his early teens.
10:36-"And I lived with Sean Pluffy Combs for a year."
10:38-"That's the crazy thing. Now, that was L.A. Reid's idea, right?"
10:41In a 2016 appearance on The Howard Stern Show, Usher recounted his time in New York with Combs.
10:46Usher recalled several names like Biggie Smalls and Lil' Kim dropping by as parties raged into the
10:51early morning.
10:52-"I went there to see the lifestyle, and I saw it. But I don't know if I could indulge and
10:58understand what I was even looking at. It was pretty wild."
11:01While Usher claims he stayed up later than Combs and his crew, he wasn't sure if he could, quote,
11:06"...indulge in some of the activities taking place."
11:08Although Usher didn't entirely understand everything going on, Combs' lifestyle was clearly, quote,
11:14"...wild," quote, "...crazy," and, quote, "...curious."
11:18When asked if he would ever send his kids to, quote,
11:20"...puffy camp," Usher gave a firm no.
11:23-"You're a dad now. Would you ever send your kid to puffy camp?"
11:25-"Hell no."
11:27Usher said this with a laugh, but the subsequent allegations and Diddy's criminal trial now lend
11:32this response a much heavier tone.
11:34Get him to the Greek.
11:36As funny as this 2010 comedy was upon release,
11:39it's hard to rewatch without thinking about how problematic several cast members have become.
11:44-"It's better. It's better that you've apologized, because now we can start to rebuild."
11:48In 2023, two women, one being his ex-girlfriend, accused Jonah Hill of abusive behavior.
11:54The same year, Russell Brand's history of sexual assault accusations caught up to him.
11:59Then there's Combs, who played hot-headed record producer Sergio Roma.
12:03-"Oh, y'all think this meeting is for me? No, no, this meeting is not for me. It's for y'all.
12:09See, see, I'm gonna be all right. I'm straight. I got villas in Brazil, Tahiti, East Hampton,
12:14West Hampton. Sergio gonna be fine."
12:17While the character was likely intended as a self-aware send-up of Combs' bombastic persona,
12:22it might have hit closer to home than the filmmakers realized. In one notable scene,
12:27a whacked-out Sergio goes on a rampage, chasing Hill and Brand's characters down a hallway.
12:32-"What are you doing? I'm all the way back to L.A."
12:35Nowadays, when we think of Combs running down a hallway,
12:38an infamous video involving Cassie Ventura immediately comes to mind.
12:42Quote,
12:43-"I'm a savage." Combs' YouTube channel posted multiple videos building hype for the 2017
12:48documentary Can't Stop Won't Stop.
12:50-"We want to hit him with that pure, uncut, 1000% who we are."
12:56If you think that title has taken on an uncomfortable sentiment,
12:59the same can be said about the aforementioned videos.
13:02In One, Combs talks about how important winning is to him,
13:05which has likely never been more true than now.
13:07-"I want to win over and over and over."
13:10In another clip, Combs sits in his office, making a deal with MTV over the phone.
13:15Combs is so excited about the outcome that he starts messing up his desk,
13:19proclaiming that he's a, quote,
13:21-"Savage," who gets whatever he wants and can't be kept down.
13:24-"Savage! I'm a savage! Oh! I'm a savage!"
13:29Taking a breather, Combs proceeds to ask what's next,
13:32although we're not sure he wants the answer.
13:35Jennifer Lopez's Mom
13:36After appearing in the Been Around the World music video,
13:39Jennifer Lopez dated Combs from 1999 to 2001.
13:43-"So handsome."
13:44In a later interview with Wendy Williams,
13:48the talk show host floated the idea of Lopez and Combs getting back together.
13:52Before Lopez could answer, she pointed to her mother,
13:55Guadalupe Rodriguez, in the audience.
13:57The horrified expression on Rodriguez's face said everything,
14:01as did a dismissive hand motion.
14:03-"Look it! Look it!"
14:06Lopez went on to talk about how Combs sent her 100 white doves,
14:10which wasn't as romantic as he might have envisioned.
14:13Even if this gesture had won Lopez back, it's safe to say her mother would not have approved.
14:18-"It's crazy everybody had, like, everybody came alive!
14:20They all had something to say!"
14:22-"Yeah, everybody has an opinion!"
14:23-"Yes! It's funny to me!"
14:24-"So, but, alright, so no puffy..."
14:26Be this due to Combs' suspected infidelity during his relationship with Lopez,
14:30or another reason, Rodriguez has strong parental instincts.
14:34Ashton Kutcher's Hot Ones interview
14:36Although he has somewhat distanced himself from Combs as of late,
14:40Ashton Kutcher was once proud to call the rapper his friend.
14:43-"Diddy party stories, they're our favorite genre of anecdote, if you have one, yeah."
14:47-"Wow, okay, I've got a lot, I can't tell."
14:49During his 2019 interview on Hot Ones, Kutcher was asked if he had any Diddy party stories to share.
14:55Kutcher had plenty, but he struggled to think of one that he could tell.
14:58-"I can't tell that one either. I'm, like, actually cycling through them."
15:02With a smile, the actor shifted the subject away from the parties,
15:06instead talking about how he first met Combs and a memorable run the two shared.
15:11While Kutcher avoided discussing any parties,
15:13there had been speculation that he could be called to testify at Combs' trial,
15:17which would have put him in a much hotter seat.
15:20-"Well, he just can't lose. Even when he's that close to humility,
15:24that, like, it becomes a driver, and so then he went out and ran the New York Marathon."
15:27The world is filled with uncomfortable lyrics.
15:30Combing through Diddy's discography, some of his music sounds almost prognostic.
15:35-"Yo, the sun don't shine forever, but as long as it's here, we might as well shine together."
15:40This includes the music video for 1998's Victory, in which the artist runs away from the authorities.
15:47Of all the songs he collaborated on, 1997's The World Is Filled may be the most unnerving to revisit.
15:54Throughout his verse, Combs sings about how it's a, quote,
15:57privilege for women to be with him, although the lyrics paint a much more troubling portrait.
16:01-"Won't you admit it, I ain't gotta talk it cause I live it. Any chick with me, believe me that's a privilege."
16:07The line, quote,
16:09"...never give up freedom," feels especially ironic and creepy.
16:12Considering Combs went on trial for sex trafficking charges,
16:16there are more ways than one to interpret the word freedom here.
16:19-"See we date him like we hate him, see him like we don't need him, treat him like we meet him, and never give him freedom."
16:25Donald Trump's, quote,
16:26"...good friend."
16:27The year was 2012. Combs was making a cameo on It's Always Sunny in Philadelphia,
16:33while a future commander-in-chief was endorsing the rapper on Celebrity Apprentice 5.
16:37-"Working for Diddy."
16:38-"Absolutely."
16:39-"I love Diddy."
16:39When Aubrey O'Day brought up Combs, Donald Trump was quick to champion him.
16:44As Trump called Combs a, quote,
16:46"...good friend," O'Day wasn't willing to comment on whether she thought he was a, quote,
16:50"...good guy."
16:51-"Is he a good guy?"
16:52-"I don't want to answer that question."
16:54-"Oh wow, I think he's a good guy. I'm gonna stick up for him."
16:56Our perceptions of Trump and Combs have drastically changed since this episode aired.
17:01Combs has reciprocated Trump's friendship in the past,
17:04although in an interview with Jimmy Kimmel, the singer said he wouldn't want to run for president like him.
17:09-"I don't know if I could be responsible for the whole country."
17:12Kimmel thought Combs would be a better leader than Trump, but the host might,
17:16just might be reconsidering that statement.
17:19His all that appearance.
17:20The docu-series Quiet On Set shined a spotlight on the dark side of several Nickelodeon shows
17:25such as All That.
17:26-"I was so excited, but I had no idea what kind of wild ride I was getting into."
17:36In 2002, Combs appeared in the sketch comedy's now infamous Lil' Fetus episode.
17:41Combs's presence has only added to the notoriety.
17:44The episode contains a few moments that aged like milk, including young girls cheering for Combs
17:50and the singer's giant head looking through a young boy's window.
17:53In the cringiest scene, Jack DeSena and Brian Hearn try to wake up Shane Lyons.
18:08They turn to Diddy, who gives them a toy helicopter and tells him to shove it down Shane's pants.
18:13When that doesn't work, Combs hands them the remote control and the boys turn the helicopter on,
18:18awakening Shane to a world of pain.
18:28You know, for kids.
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18:43Justin Bieber's 48 Hours with Diddy
18:48In 2009, a video was posted to Justin Bieber's YouTube page featuring the teenage singer and Diddy.
18:59Addressing the camera, Combs said Bieber would be hanging out with him for 48 hours.
19:04Combs wouldn't divulge exactly what they would be up to,
19:06but he presented it as a dream come true for a boy of Bieber's age.
19:10It seemed innocent, even cool at the time.
19:13I don't really, I don't have legal guardianship of him, but for the next 48 hours,
19:17he's with me, so um, and yeah, and we gonna go full, buck-full crazy.
19:2315 years later though, we can't help but read more into the awkward word choice.
19:28For the record, Combs says quote,
19:30buck-full crazy, but it sounds like something else.
19:33The two reunited in another video where Combs mentions they haven't seen each other in a while.
19:38This prompts Bieber to give him a fake number.
19:49What Diddy moments do you look at differently? Let us know in the comments.
19:52What's one misconception about you?
19:54There are no misconceptions about me.
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