Sketchy Things About Diddy And Ashton Kutcher's Friendship

As high-profile celebrities, it's not surprising that Sean "Diddy" Combs and Ashton Kutcher not only run in the same circles but are also tight friends. The two made an appearance on "The Late Late Show With James Corden" and recalled how they first met. "I was doing 'Making the Band' and he was doing 'Punk'd' and I gave him a call one day and I said, 'I heard that you are gonna punk me and I just don't think that's a good idea,'" Diddy shared. Kutcher's version was much different and he stated that the rapper wasn't as nice. "If you do that, that will not end well for you," Kutcher claimed Diddy told him. Following the conversation, they got so close they even hit the gym together, sparking enough motivation for Diddy to tackle the New York City Marathon.

Diddy and Kutcher's relationship isn't all wholesome, however. Although they're seemingly quite close, they don't follow each other on Instagram. While it's unclear if they ever did at one point, Kutcher is reportedly distancing himself from his bestie amid Diddy's sexual assault and human trafficking allegations. After getting dragged for defending Danny Masterson, his move isn't surprising, as Kutcher's friendship with Diddy is pretty murky.

Ashton Kutcher is worried he'll get dragged into Diddy's legal mess

While no criminal charges have been formally leveled against Sean "Diddy" Combs, the rapper's houses were raided by Homeland Security in March 2024 in what is thought to be an ongoing investigation regarding sex trafficking. Celebrities like 50 Cent and Aubrey O'Day spoke out against Diddy, but members of his inner circle, including Ashton Kutcher, have been noticeably tight-lipped. "There is no way in hell Ashton or Mila will be showing any sort of public support for Diddy right now," a source shared with the Daily Mail. "Regardless of Ashton's long history with him, he has distanced himself from Diddy since Cassie's lawsuit, and 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," the insider continued.

Kutcher and Mila Kunis offered an apology after getting called out for writing a letter to the courts defending Danny Masterson's character before his sentencing for sexual assault. "The letters were not written to question the legitimacy of the judicial system or the validity of the jury's ruling," Kunis said in their apology video. Kutcher addressed the shady move and stated, "They were intended for the judge to read and not to undermine the testimony of the victims or re-traumatize them in any way. We would never want to do that. And we're sorry if that has taken place."

Ashton Kutcher founded an anti-human trafficking organization

In 2009, Ashton Kutcher and his then-wife, Demi Moore, co-founded the charity Thorn in an effort to stop child trafficking after watching a documentary on Dateline. "Those Cambodian kids were 7, 8, 9 years old. I started asking around, and people said to me, 'Oh, no, it's happening right here in Los Angeles,'" Kutcher told W Magazine. At the time, he was the board chairman, but after the Danny Masterson debacle, he made the decision to resign. "After my wife and I spent several days of listening, personal reflection, learning, and conversations with survivors and the employees and leadership at Thorn, I have determined the responsible thing for me to do is resign as Chairman of the Board, effectively immediately," the "Jobs" actor wrote in a statement posted to the organization's website. "I cannot allow my error in judgment to distract from our efforts and the children we serve," Kutcher added.

Now that Kutcher is tied to Sean "Diddy" Combs amid the rapper's sexual assault and human trafficking allegations, his efforts are eyebrow-raising — to say the least. "So now two close friends of Ashton are sex predators...okayyyy," a Reddit user shared. Another wrote, "Ashton Kutcher being the face of an organization [whose] purpose was to stop sex trafficking, being close friends with so many rapists and predators is so menacing." It's no wonder Kutcher is keeping his head down when it comes to Diddy these days.

Ashton Kutcher attended many of Diddy's wild parties

Sean "Diddy" Combs gained a reputation for his star-studded "White Party" hosted yearly in the Hamptons, and in 2009, his BFF Ashton Kutcher acted as his co-host. While the gathering has since died down, we're guessing Kutcher wishes he had passed on the invitation given the recent turmoil involving Diddy.

The goings-on at Diddy's parties must have been pretty debaucherous as Kutcher couldn't even divulge what transpired during his appearance on "Hot Ones." When asked about the "Bad Boy" rapper's get-togethers, Kutcher replied, "Wow, okay I've got a lot — I can't tell." As he dug up his memories, he laughed and added, "I can't tell that one either."

One of Diddy's parties took a dark turn in 2022 when his son Christian Combs allegedly sexually assaulted a staff member of the yacht that the rapper chartered. Grace O'Marcaigh claimed that Christian forced her to drink alcohol that she suspected was laced with something and was groped and pressured to perform sexual acts but managed to escape the ordeal.

Ashton Kutcher and Diddy are competitive

Friendly competition between friends is normal but it seems Ashton Kutcher admitted on "Hot Ones" that Sean "Diddy" Combs wants to win at all costs. "He comes over to go for a run, about halfway through the run, he's like, 'I'm running out of gas right now,'" Kutcher recounted. "But we had paparazzi all around us at the time and he was like, 'You gotta slow down ... but make it look like you're not slowing down because I don't wanna look like I'm not gonna be able to finish this thing.' And he was losing it," he continued. The "Punk'd" creator shared that Diddy was so upset he got gassed out that he resolved to run the marathon that year. "He just can't lose, even when he's that close to humility," Kutcher added.

Diddy confirmed that it was that day that spurred him to train. He told James Corden, "We've always been competitive in a positive way, always pushed each other to achieve our dreams and to think out of the box." However, Diddy admitted it was those unflattering paparazzi shots that mortified him enough to kick his fitness into high gear. Kutcher shaded him by joking that while Combs struggled, he was caught running with ease.

Diddy considers Ashton Kutcher part of his Rat Pack

When Ashton Kutcher made the 2010 Time 100 list in 2010, Sean "Diddy" Combs referred to their partying heyday and stated, "For a while, with Jamie Foxx, we were a rat pack, hanging out, going to clubs. I remember one night he was with Demi, maybe for the first time, and a couple of weeks later he called to tell me he was in love." Combs went on to say, "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."

That wasn't the only difference between Combs and Kutcher. In an interview with The Daily Herald (via The Daily Beast), Kutcher revealed, "Our friendship has helped me become aware of the fact that people are becoming comfortable with something that's still very uncomfortable." He shared that people would wonder why he and Combs were friends since their backgrounds were so different. "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 was a white hip hop artist from New York, nobody would have noticed," Kutcher explained. Despite having an unconventional friendship, the two have remained close over the years, which has seemingly changed since Diddy's recent troubles.