Diddy federal investigation sparks interest in famous friends, interviews resurface: ‘A lot I can’t tell’

Sean “Diddy” Combs cultivated an elite roster of close confidantes through the years as one of the most in-demand music producers in the entertainment industry.

Two weeks after Homeland Security Investigation (HSI) officers raided his residences in Los Angeles and Miami in connection to a federal human trafficking investigation, Diddy’s relationships have been put under the spotlight.

Between famous exes and fast friendships turned into long-lasting allies, we take a look at a few of the power players Diddy has befriended over the years.

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Ashton Kutcher

Between famous exes and fast friendships turned into long-lasting allies, we take a look at a few of the people Diddy has befriended over the years. (Getty Images)

The “That ‘70s Show” actor first bonded with Combs over their shared love of pranking people. During an appearance on “Hot Ones” in 2019, Kutcher was overwhelmed with his memories and couldn’t pick one Diddy “party story” to share.

“Wow, I’ve got a lot I can’t tell. I can’t tell that one either,” Kutcher said. “Actually cycling through them … Our relationship is really bizarre because it started overPunk’d’ cause he’s like, ‘Yo, you can’t punk me.’ I was like, ‘I don’t know what to tell you, everybody’s on the table,'” he said. Diddy apparently said, “Not me, I’m off the table.”

“So, that started our conversation,” Ashton said.

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“We became fast friends. We used to hang out and watch football together,” Kutcher recalled. “He came over, and I was like, ‘I’m going for a run’ and he was like, ‘I’ll go for a run with you.’ So he comes over to go for a run. About half way through the run, he’s like, ‘Yo I’m running out of gas right now,’ but we had like paparazzi all around us at the time. He’s like, ‘You’ve gotta slow down, but make it look like you’re not slowing down cause I don’t want to look like I’m not gonna be able to finish this thing.'”

Sean Combs and Ashton Kutcher hug in suits

Ashton Kutcher said he formed a fast friendship with Diddy. (Getty Images)

Rapper Sean Combs runs across finish line of New York marathon

Diddy completed the New York marathon on Nov. 2, 2003. (Getty Images)

Kutcher said they finished their run together, but Diddy was so upset by his run that he decided to run the New York marathon.

“He started immediately training for the New York marathon,” Kutcher said. “He just can’t lose. Even when he’s that close to humility, that becomes a driver.”

Usher

Diddy helped mentor Usher and brought the then-teenage R&B singer to the East Coast to live with him for a year when he broke into the music scene.

“I moved to New York City and I lived with Sean ‘Puffy’ Combs for a year,” Usher told Howard Stern in a resurfaced clip from 2016.

Stern mentioned, “That was L.A. Reid’s idea, right? We’re sending you to something called Puffy Flavor Camp.”

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“In the ‘90s; do you understand what that’s like?” Usher said, before Stern quipped, “Puffy’s place was like just filled with chicks and orgying like non-stop, right?

Sean Combs wears pinstripe suit with singer Usher.

Usher worked with Sean Combs (pictured in 2002) in the beginning of his career. (Kevin Mazur)

“Nah, not really. It was curious. I got a chance to see some things,” Usher said. “Yeah, but you were 13. What were you seeing?” Howard asked.

The Atlanta-based musician noted, “I went there to see the lifestyle, and I saw it. And it was… But I don’t know if I could indulge and understand what I was even looking at. It was pretty wild. It was crazy.”

Co-host Robin Quivers chimed in, “So nobody tried to, you know, some woman didn’t come along…” 

Usher laughed before adding, “I didn’t say that. What I did say is that there were very curious things taking place, and I didn’t necessarily understand it.”

He noted that the parties were filled with industry heavy-hitters, including, “Biggie Smalls was there, Lil Kim, Craig Mack… Faith Evans, Jodeci, Mary J. Blige.”

Robin asked if his parents were “OK with everything,” to which Usher said, “They didn’t know nothing about this s—. I was having a good time.”

Nick Cannon

The “Masked Singer” host shared his struggles with friendships on a recent episode of his “Counsel Culture” show. Cannon was asked, “What do you think about Diddy?” and said he found it difficult to respond to questions about people he knows. 

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“It was either ‘The Breakfast Club’ or Angela Yee or something, and they asked me about Puff, and I answered it as honestly as I knew how to answer it,” he said. “I know these people. They’re not just public figures to me, so I have to almost do this dance about when it comes up, because just as much as I know Diddy, I know Cassie.”

Cannon was referring to the lawsuit Cassie filed in November where she accused Combs of raping her in her own home, enduring “over a decade” of his “violent behavior and disturbed demands” in addition to allegedly forcing her to have sex with male prostitutes while he watched and filmed. 

Nick Cannon and Diddy wear black suits to a party

Nick Cannon defended his friendship with Sean “Diddy” Combs following a lawsuit Combs’ ex-girlfriend Cassie filed and dismissed last year. (Getty Images)

One day after she filed the claim, Combs and Cassie, legally known as Casandra Ventura, came to an amicable resolution, and she dropped the lawsuit. 

Cannon defended his choice to say he was “praying for Cassie,” and stated, “This is someone who was hurt, who was victimized.” He added, “But then when this question goes a little bit further, like, so what about Puff? I don’t know how to feel about that. When I was going through my stuff, someone that called, checked on me, stood by me, stood up for me, and I was like, what do I owe?”

In July 2020, Cannon was fired by ViacomCBS after a decades-long working relationship for spreading “anti-Semitic conspiracy theories” and “hateful speech” made on an episode of his YouTube podcast “Cannon’s Class.” 

Diddy almost immediately fired back and offered Cannon a job at his Revolt TV company. 

“We got your back and love you and what you have done for the culture,” Diddy tweeted at the time. “We are for our people first!!! For us! By US! Let’s go!!!”

Justin Bieber

A video showing 48 hours with Diddy and a teenage Justin Bieber resurfaced shortly after the rapper’s homes were raided in connection to the federal human trafficking investigation.

Diddy sings with Justin Bieber

Diddy stayed quiet on antics with Justin Bieber in resurfaced video. (Getty Images)

“He’s having 48 hours with Diddy, him and his boy,” the rapper said in the video shared to Bieber’s YouTube account 14 years ago. “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.”

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“I have been given custody of him,” Diddy said. “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.”

“I don’t have legal guardianship of him,” he explained, referring to Bieber, “but for the next 48 hours he’s with me, and we’re gonna go full crazy.”

“Let’s go get some girls,” Bieber told Diddy when asked what he wanted to do. “Man after my heart,” Diddy responded. “That’s what I’m talking about.”

Jennifer Lopez

Combs and Lopez dated from 1999-2001, but ultimately split due to his alleged infidelity. She told Vibe in 2003, “I was in this relationship with Puff [Combs] where I was totally crying, crazy and going nuts. It really took my whole life in a tailspin.”

Singer Jennifer Lopez wears stunning green Versace gown with boyfriend Sean Diddy Combs

Sean and Jennifer dated for two years before calling it quits in 2001. (Vince Bucci)

In 1999, Lopez was with Combs and rapper Shyne when gunfire broke out, injuring three people, including a woman who was shot in the face. She fled with Combs in his Lincoln, but the couple was later pulled over by the NYPD for running a red light.

A gun was found in the vehicle, and Lopez and Diddy were arrested. Lopez was let go, but Diddy and Shyne were each charged with multiple offenses. While Combs was found not guilty at trial, Shyne was convicted on five of eight counts and was sentenced to 10 years in prison. 

Mariah Carey

The “Emotions” singer formed a strong bond with up-and-coming artist, Sean Combs, who had just launched his Bad Boy Records label. She wrote in her 2020 memoir, “The Meaning of Mariah Carey,” that her ex-husband, former Sony Music president Tommy Mottola, often showed racial microaggressions.

Once when Tommy was talking about Combs, she recalled him saying, “‘Puffy will be shining my shoes in two years.’ It was one of the very few times I stood up to Tommy, telling him that what he had said was blatantly racist. I was pissed.”

Singer Mariah Carey holds a microphone on stage with Diddy

Mariah Carey and Diddy collaborated on music together. (Getty Images)

At a dinner, the head of Epic Records asked Mariah her thoughts on Puffy.

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“The table got quiet as I leaned in and gave my honest assessment: that Puff and Bad Boy were definitely where modern music was headed,” she wrote. 

Tommy left the table and paced around the restaurant before returning to the room. “Still vibrating with rage, he slammed his first on the table and announced, ‘I just want everybody to know that THANKSGIVING IS CANCELLED!'”

Mary J. Blige

Diddy produced Mary J. Blige’s first two albums when she was a rising star out of Yonkers. She became the youngest and first female artist signed to Uptown records at 18 years old, thanks in part to Diddy’s mentor, Andre Harrell.

“Puff was a huge inspiration for me,” she told People magazine last year. “He wanted all of this for me more than I wanted it myself.”

Sean

Mary J. Blige praised Combs for being a “huge inspiration” to her. (Photo by Todd Williamson/NBC/NBCU Photo Bank via Getty Images)

Combs noted, “More than being my sister and my best friend, she will forever be a pioneer and the Queen of Hip-Hop Soul, who remains an unstoppable force that can accomplish anything she sets her mind to.”

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Blige, who had Diddy present her the Hollywood Walk of Fame star in 2018, added, “I was not as ambitious as Puff. When I met him, I was afraid of success, afraid to do anything that could put so much attention on me. When you come from where I come from, you’re scared to be ambitious. You’re scared to want more. And then when I met him, he was the complete opposite. 

“He was such a good thing for me because I needed what he had, to be excited to be seen, to have the lights on him. But it took some years to grow into that.”

Lil’ Kim

The Bad Boys always had one queen bee: Lil’ Kim. Discovered by Notorious B.I.G., Kim is known as the queen of rap and main member of the “Junior M.A.F.I.A.”

She’s collaborated with many of Diddy’s famous friends, and toured with Combs multiple times.

Music mogul Sean Combs wears all black on red carpet with Notorious B.I.G. and Lil Kim.

Combs found fame as a producer for the late Notorious B.I.G. and Lil Kim. (Getty Images)

In November, she gave Diddy a birthday shoutout, writing, “Love u 4 life big bro HBD @diddy.” 

DJ Khaled

DJ Khaled and Combs have a special bond over their shared love of music and the state of Florida. When DJ Khaled was involved in a jet ski accident, he found help from his friend Diddy who let him clean off and relax in his pool. 

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In addition to being neighbors, the pair also worked together on the reality singing competition series, “The Four.”

Years later, knowing Khaled was pursuing a love for golf, Diddy surprised his friend with a new, $40,000 golf cart. “I want to say thank you, brother. I never get gifts,” Khaled told Diddy.

“If you gonna be the No. 1 in golfing, I gotta make sure you the No. 1 in the golf cart,” Diddy said.

Naomi Campbell

Diddy and Naomi Cambell were rumored to be in a relationship back in 2002. Despite the purported romance fizzling, they remained friends and have been pictured together dozens of times around town and at fundraisers. 

Supermodel Naomi Campbell sits next to Diddy in the backseat of a limo.

Diddy left Naomi Campbell’s 54th birthday party in London with the supermodel. (Getty Images)

He was most recently spotted attending the supermodel’s 54th birthday party at Lavo in London in November 2023.

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