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What incident happened between Charlie Sheen and Dax Shepard that spanned 20 years?


The Two and a Half Men actor had 'been carrying around' something he wanted to apologize to Dax Shepard for during his appearance on Armchair Expert


Dax Shepard and Charlie Sheen© Getty Images
Tess Hill
Tess HillNews and Features Writer
October 7, 2025
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If there's something Dax Shepard, 50, loves, it's bringing up an awkward moment from years ago to his guests on his podcast, Armchair Expert. So it was a lovely surprise when this week's interviewee, Charlie Sheen, 60, apologized for an incident that occurred over 20 years ago, the podcast host was downright giddy. During the episode released on Monday, October 6, the Two and a Half Men actor couldn't help but share his regret over an interaction that happened two decades ago.

"There's something I've been carrying around," Charlie revealed to Dax. "I was a dick to you one night. Not cool. Like an [expletive] 5,000." Dax had no idea what his guest was talking about, so he responded: "Tell me because it's so bizarre. I don't remember that." Charlie explained that after a conversation with Dax, he recalled thinking that he'd "make [things] right…the next day or the next week or the next month."

20 years later, the actor finally had the chance to make amends. Charlie explained that during an A.A. meeting he shared his frustrations about navigating Halloween with young children. "We were sharing how Halloween with super tiny children is not fun. It's just not," Charlie 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?"

Nicolas Cage and actor Charlie Sheen on June 16, 1990 party at Bar One Nightclub in West Hollywood, California© Getty
In his memoir, Charlie details friendship with Nicolas Cage.

The Platoon actor remembered Dax opening up later about his Halloween experience. "[You were] like, 'Yeah, no, we had a great time. Went to a couple of parties this time,' and you were…giving the fun version of Halloween. In the middle, I said, 'Try it with [expletive] kids, dude.' And it was so inappropriate and unnecessary and uncalled for. So 20 years later, apologies."

Jon Cryer,  Angus T. Jones, and Charlie Sheen for the television comedy 'Two and a Half Men'© Getty Images
"Two and a Half Men" ran from 2003-2015

Dax immediately accepted Charlie's apology, but made it clear it was unnecessary. "There's a lot of people I've made amends to," the podcast host explained. "Thank God I did. And they were really hurt and that repair had to happen." Dax continued: "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 [expletive].'"

photo of dax shepard kissing kristen bell on the head© WWD via Getty Images
Dax is married to Nobody Wants This actress Kristen Bell

Both Charlie and Dax have been open about their struggles with drug and alcohol abuse. The Ferris Bueller's Day Off actor was on Armchair Expert to promote his memoir, The Book of Sheen, and his documentary, aka Charlie Sheen, which dive deep into his public struggles with addiction. For his part, Dax regularly shares about his historic issues with addiction, even coming clean about a relapse on a podcast episode titled "Day 7."

Dax Shepard and Monica Padman attend Amazon unBoxed 2024 at Austin Convention Center© Getty Images
Dax and Monica Padman launched Armchair Expert in 2018

On Armchair Expert, Dax and his co-host Monica Padman dive into the dark side of addiction, which often leads to the former apologizing for awkward moments made when he was not sober. But, both Charlie and Dax are sober now. And they face their sobriety in similar ways. Charlie explained on the podcast: "I've got more days behind me than in front of me and that's fine. 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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