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Charlie Sheen issues apology to Dax Shepard 20 years after insult

Shepard didn’t recall the interaction and brushed off Sheen’s apology

Caitlin Hornik
in New York
Monday 06 October 2025 18:50 BST
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Charlie Sheen has apologized for an unpleasant interaction with Dax Shepard that has plagued him for 20 years.

While appearing as a guest on Shepard’s Armchair Expert podcast, Sheen told the host: “There's something I've been carrying around. I was a d*** to you one night. Not cool. Like an a**hole 5,000.”

Shepard appeared confused, not recalling the decades-old interaction. Sheen — father to Cassandra Estevez, 40, with Paula Profit; daughters Sami, 21, and Lola, 20, with Denise Richards; and twin boys Bob and Max Sheen, 17, with Brooke Mueller — said it took place around Halloween while he was navigating parenting his young kids.

“We were sharing how Halloween with super tiny children is not fun. It's just not,” Sheen began. “I mean, it is and it isn't. It's fun for the photo on the fridge later. I was kind of in a pissy mood in my share, and I was bitching about Halloween and just zero gratitude about anything, you know?”

Explaining that Shepard had revealed his own Halloween stories, Sheen continued: “He was like, ‘Yeah, no, we had a great time. Went to a couple of parties this time,’ and you were like giving the fun version of Halloween. In the middle, I said, ‘Try it with f***ing kids, dude. And it was so inappropriate and unnecessary and uncalled for. So 20 years later, apologies.”

Charlie Sheen has apologized to Dax Shepard for comments he made 20 years ago
Charlie Sheen has apologized to Dax Shepard for comments he made 20 years ago (Getty)

Sheen recalled wanting to make it right “the next day or the next week or the next month.”

“And here we are 20 years later,” he said.

Shepard brushed off the incident and accepted Sheen’s apology, before opening up the conversation to the broader topic of making amends with those he felt he has wronged.

“More often than not, I've called people and said, ‘You know, I did this and I did that.’ And they're like, ‘I didn't give a f***,’” Shepard said.

“But I'm living with this notion that this person f***ing hates me over it and they felt betrayed by it. I do think that's an interesting part of making amends is like, you've built up a lot of it in your mind that isn't really there. It's just you're holding it. They weren't.”

Sheen’s apology to Shepard comes weeks after he expressed his desire to make amends with his estranged former co-star, Jon Cryer.

From 2003 to 2011, the pair co-led Two and a Half Men, helping to make it one of the most popular sitcoms in the world. However, Sheen was infamously fired after exhibiting erratic behavior and making disparaging remarks about the show’s creator, Chuck Lorre.

Sheen also wishes to make amends with his former to co-star Jon Cryer.
Sheen also wishes to make amends with his former to co-star Jon Cryer. (Getty Images)

Sheen recently released a memoir, The Book of Sheen, and a Netflix documentary, aka Charlie Sheen, the latter of which Cryer appeared in, without having spoken to Sheen first.

“The only person I didn’t call personally to participate in the doc was Jon,” Sheen told People ahead of the film’s release. The two-part series also includes Sheen’s ex-wives Richards and Mueller, his longtime friend Sean Penn, several family members, as well as Cryer and Lorre.

“And the only reason I didn’t call him was because I didn’t have the right number for him, so the director reached out to him. But when I saw everything that Jon spoke about, so honestly and very compassionately, I wrote to him and I said, ‘Hey, thank you for your contributions, and I’m sorry we didn't connect personally. I hope to see you around the campus.’”

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