Charlie Sheen Apologizes to Dax Shepard 20 Years Later for Being an 'A 5000' Rachel McRadyOctober 7, 2025 at 12:13 AM 0 Mike Kirschbaum/TKO Worldwide LLC via Getty; Jason Bollenbacher/Getty Charlie Sheen and Dax Shepard Charlie Sheen appeared on Dax Shepard's Armchair Expert podcast on Oct.
- - Charlie Sheen Apologizes to Dax Shepard 20 Years Later for Being an 'A------ 5000'
Rachel McRadyOctober 7, 2025 at 12:13 AM
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Mike Kirschbaum/TKO Worldwide LLC via Getty; Jason Bollenbacher/Getty
Charlie Sheen and Dax Shepard -
Charlie Sheen appeared on Dax Shepard's Armchair Expert podcast on Oct. 6
He took the opportunity to apologize to Shepard for some comments he made 20 years ago
Shepard had no memory of the exchange
Charlie Sheen is making amends over a conversation he had with Dax Shepard 20 years ago.
The 60-year-old Two and a Half Men actor served as a guest on the Monday, Oct. 6 episode of Shepard's Armchair Expert podcast, where he gave the co-host an apology decades in the making.
"There's something I've been carrying around," Sheen admitted to Shepard, 50. "I was a dick to you one night. Not cool. Like an a------ 5,000."
Shepard was baffled by the confession, saying, "Tell me because it's so bizarre. I don't remember that."
Sheen recalled thinking, "the next day or the next week or the next month," he had had to "make that right," adding, "And here we are 20 years later."
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According to Sheen, the incident occurred at Halloween when Sheen was navigating having small children.
"We were sharing how Halloween with super tiny children is not fun. It's just not," Sheen said. "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?"
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Brooke Mueller and Charlie Sheen with Sheen's daughters Sami Sheen and Lola Sheen.
Sheen noted that Shepard then opened up about his own Halloween antics at the time.
"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------ kids, dude. And it was so inappropriate and unnecessary and uncalled for. So 20 years later, apologies."
Shepard brushed off the forgotten moment, telling Sheen, "No problem," and acknowledging how often apologies are more for the apologizer than the person being apologized to.
"There's a lot of people I've made amends to. Thank God I did. And they were really hurt and that repair had to happen," Shepard, who has been open about his struggles with alcohol and substance abuse, said. "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---. But I'm living with this notion that this person f------ 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."
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Dax Shepard talks at the Natural Products Expo West 2025 in March.
Sheen is dad to daughters Cassandra Estevez, 40, with ex Paula Profit, and Sami, 21, and Lola, 20, with ex Denise Richards and twin boys Bob and Max Sheen, 17, with ex Brooke Mueller.
The actor has been open about his tense relationship with Sami, who has spoken out against him on TikTok.
"There's some stuff going on with Sami, but we'll fix it," he told PEOPLE in September.
Sheen added of his milestone 60th birthday, "I've got more days behind me than in front of me and that's fine."
"That's the deal we get when we show up [on Earth]," he continued at the time. "But what I try to tell my kids is, 'Dude, you're going to be here so long after I'm not. So try to hang on to at least 10% of what I'm saying. I guarantee it will come in handy somewhere, I promise it.'"
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