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Diddy’s Celebrity Connections Through the Years: From Friends to Collaborators

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Justin Bieber, Sean ‘Diddy’ Combs and Will Smith. Getty Images (3)

Sean “Diddy” Combs made his music industry debut in the early 1990s and has racked up a long list of collaborators and famous friends.

Over the years, Diddy used his power in the industry to create longtime relationships with various rappers.

However, as of late, Diddy has faced his fair share of controversy. The music mogul’s two homes in Los Angeles and Miami were raided by Homeland Security in March 2024, reportedly in connection with federal sex trafficking allegations. (Diddy has been accused of sexual assault by multiple men and women since ex-girlfriend Cassie filed a lawsuit against him — which has since been settled — in November 2023. He has since denied all of the allegations.)

“Earlier today, Homeland Security Investigations (HSI) New York executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners,” Homeland Security told Us in a statement. “We will provide further information as it becomes available.”

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Diddy’s lawyer Aaron Dyer told Us in a statement that the raid showed “a gross overuse of military-level force as search warrants were executed.” He added: “There is no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated.”

Dyer called the raids an “unprecedented ambush” and “a premature rush to judgment of Mr. Combs and is nothing more than a witch hunt based on meritless accusations made in civil lawsuits,” in part.

The statement made it clear that Diddy was “never detained but spoke to and cooperated with authorities” amid the situation. “There has been no finding of criminal or civil liability with any of these allegations. Mr. Combs is innocent and will continue to fight every single day to clear his name.”

Keep scrolling to look back at Diddy’s friends and associates over the years:

Lil’ Kim

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Johnny Nunez/WireImage

The two musicians have always been in the same musical circles. In November 2023, Kim shared an Instagram tribute to Diddy, writing, “Love u 4 LiFe Big Bro! 😘❤️😻 HBD @diddy.”

Rick Ross

Ross and Diddy have been collaborators for years. In 2023, their friendship made some headlines as Diddy sent the fellow rapper a golf cart as a housewarming gift after Ross’ move to Miami.

Diddy s Ups and Downs Over the Years Name Changes Lawsuits Home Raid and More 473

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DJ Khaled

Instagram users will remember the 2017 jet ski debacle featuring Khaled riding over to Diddy’s and subsequently getting stuck. “I’m OK, I made it to Diddy’s house,” he said after multiple videos recounting the near emergency.

In 2022, Diddy honored his “lovable” friend at Khaled’s 47th birthday party. “I appreciate you loving me as a friend. You was king down here in Miami and look at you now. God did,” Diddy said.

Their friendship has continued, and Diddy even gifted Khaled with a golf cart in April 2023.

Justin Bieber

Fans resurfaced a video in March 2024 that showed a 15-year-old Bieber hanging out with Diddy for 48 hours.

“Where we hanging out and what we’re doing we really can’t disclose,” Diddy could be heard saying in the video. “But it’s definitely a 15-year-old’s dream.”

In a second resurfaced video, apparently taken months later, Diddy could be heard asking Bieber why they haven’t “been calling me and hanging out with me the way we used to.”

Mariah Carey

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Stephen Lovekin/WireImage for Paul Wilmot Communications

Carey released her The Meaning of Mariah Carey memoir in 2020, and name-dropped Diddy ­— specifically recalling one time her former manager and ex-husband Tommy Mottola allegedly made racial comments about the rapper.

“‘Puffy will be shining my shoes in two years,'” he allegedly said, per the book, referring to Diddy’s former moniker Puff Daddy. “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.”

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Over the years, the duo have been photographed together at various events.


Usher famously lived with Diddy at age 14 in 1994.

“I got a chance to see some things,” Usher recalled during a 2016 interview on The Howard Stern Show. “I don’t know if I could indulge and even understand what I was looking at.”

Usher said the “place was filled with chicks and orgying nonstop.”

Will Smith

The pair both ruled the rap scene in the ‘90s. Diddy seemingly came to Smith’s defense years later after the actor slapped Chris Rock during the 2022 Oscars.

“I just want to say, let’s make some noise for Amy [Schumer], Regina [Hall], Wanda [Sykes]!” the rapper said during the same awards ceremony, referring to the show’s hosts. “Gotta give it up for Wanda. I did not know that this year was going to be the most exciting Oscars ever.”

He added: “OK, Will and Chris, we’re going to solve that like family at the Gold Party, OK? But right now we are moving on with love. Everybody make some noise!”

Ashton Kutcher

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Stefanie Keenan/Getty Images for WeWork

Kutcher and Diddy actually have a longtime friendship that spans back to the early 2000s.

“It started over Punk’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.’ So, that started our conversation,” Kutcher recalled on “Hot Ones” in 2019, saying that this interaction led to them becoming “fast friends.”

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