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Ashton Kutcher and Sean “P. Diddy” Combs‘ relationship spans decades. They developed a friendship after Kutcher planned to put Combs on Punk’d. Now, we’re looking back at an old interview of Combs and Kutcher in light of Homeland Security raiding two of Combs’ properties in March 2024. Here’s what Kutcher once said about Combs lacking “humility.”

Ashton Kutcher described a time when P. Diddy refused to show ‘humility’

Ashton Kutcher and Combs seem like unlikely friends, but they developed a close friendship that involved a lot of one-on-one time. In 2018, the movie star and the hip-hop mogul sat down with James Corden on The Late Late Show With James Corden and discussed their relationship. Combs explained that they met after he caught wind of Kutcher’s wanting to put him on MTV’s prank TV show Punk’d.

“I gave [Kutcher] a call one day and said, ‘I heard that you are going to punk me, and I just don’t think that’s a good idea,’” Combs told Corden.

“I kind of don’t think that that’s the way you said it,” Kutcher laughed, implying that Combs may have threatened him.

Kutcher discussed his friendship with Combs during his interview with Hot Ones. He described a time he went for a run, and Combs decided to come with him. “About halfway through the run, he’s like, ‘Yo, I’m running out of gas right now,'” Kutcher described of Combs. “But we had paparazzi all around us at the time. He’s like, ‘You gotta slow down, but make it look like you’re not slowing down because I don’t want to look like I’m not gonna be able to finish this thing.’ He was losing it.”

After the run, Kutcher said Combs was “so upset” by his running performance that Combs immediately signed up for the New York City Marathon. “He just can’t lose,” Kutcher continued. “Even when he’s that close to humility, it becomes a driver. And so then he went out and ran the New York marathon.”

Ashton Kutcher said people didn’t understand why he and the hip-hop mogul spent time together

Sean 'P. Diddy' Combs hugging Ashton Kutcher on stage while holding an award in 2003
Sean ‘P. Diddy’ Combs and Ashton Kutcher | Chris Polk/FilmMagic
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People in Hollywood didn’t necessarily understand Sean “P. Diddy” Combs’ friendship with Ashton Kutcher. In 2005, Kutcher explained that racism was heavily at play.

“When I was hanging out with Sean, people did not understand why this Iowa farm kid went out with this hip-hop mogul from New York,” Kutcher told The Daily Herald, according to the Daily Beast. “But it wasn’t that he was a hip-hop mogul and I was a farm kid; it was because he was Black, and I was white. It was that simple. If he were a white hip-hop artist from New York, nobody would have noticed.”

In 2010, when Time included Kutcher in their roundup of the 100 most influential people of the year, Combs showed his support. “He is a sounding board for me,” Combs said. “Like me, he’s a mogul — a new-media mogul. But we are yin and yang: I am in your face, but he is understated, cool, suave.”

Kutcher and his wife, Mila Kunis, likely won’t show public support for Sean ‘P. Diddy’ Combs

Despite Ashton Kutcher’s close friendship with Sean “P. Diddy” Combs, the public shouldn’t expect Kutcher and his wife, Mila Kunis, to support Combs after the Homeland Security raid publicly.

“There is no way in hell Ashton or Mila will be showing any sort of public support for Diddy right now,” a source told DailyMail.com. “Regardless of Ashton’s long history with him, he has distanced himself from Diddy since Cassie’s lawsuit, even more so in the wake of the new ones. Mila will not let Ashton be in any sort of contact. He is expecting a subpoena as they have been good friends for 20 years.”

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