heartbreak and hindsight

Charlie Sheen shares the devastating moment when he lost a role to Tom Cruise


The 60-year-old actor looked back on that career-shifting moment


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Shirley GomezSenior Writer
OCTOBER 30, 2025 5:45 PM EDT

Charlie Sheen just dropped a Hollywood story that’s equal parts heartbreak and hindsight, the day he found out he didn’t get the lead in "Born on the Fourth of July." During his candid chat on "In Depth with Graham Bensinger," the 60-year-old actor looked back on that career-shifting moment when his brother Emilio Estevez broke the news: Tom Cruise, not Sheen, would play Vietnam vet Ron Kovic in Oliver Stone’s 1989 classic.

“Sheen thought he was a lock.” After all, he’d just starred in "Platoon" and "Wall Street," both Oliver Stone films. So when Emilio called with a cryptic “Hey man, you sitting down?”, Sheen braced for tragedy, not casting news. “‘Cruise is doing 'Born on the Fourth,’” Emilio told him.

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Emilio Estevez and Charlie Sheen at the premiere of "Rated X" on April 27, 2000.

Sheen’s reaction was a mix of disbelief and dry humor. “I love that Emilio thought I needed to sit down to hear that. Like, what are we doing here? It’s a movie.” But beneath the humor, it stung.

A Betrayal That Hit Close to Home

Sheen admitted there was a “betrayal factor.” Stone had once made it seem like Sheen had the part. They even met with the real Ron Kovic over dinner. Then the communication stopped. “I reach out to Oliver and I’m told he’s in Cuba,” Sheen said. “Whatever. This is like 1988 or ’89, right? I’m like, ‘Okay, well, tell him I’m looking for him.’”

Eventually, the silence became the answer. “You can’t lose something you never had,” he said, reflecting. “There was no contract — just a handshake.”

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Thirty-five years later, Charlie Sheen isn’t bitter. He’s just telling it unfiltered, a little funny, and surprisingly gracious.

The Awkward Bar Confrontation

The story didn’t end there. Years later, Sheen ran into Stone at a bar. Both men were tipsy enough to bring up the elephant in the room.

Stone told Sheen he felt the actor had “lost interest” in the project. Sheen shot back with brutal logic: “How do you know how much interest I lost if we never talked about it again?”

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Instead of holding a grudge, he gave Cruise his flowers.

Here’s where Sheen surprises everyone. Instead of holding a grudge, he gave Cruise his flowers. “When someone gets a job and does that with it, you just go, ‘Of course,’” he said. “You don’t sit there going, ‘I’d have done that better.’ No — go f–k yourself. That’s brilliant. He should’ve won the Oscar.”

Cruise did earn an Oscar nomination for his intense portrayal of Kovic, a performance that cemented his transition from heartthrob to serious actor.

The Butterfly Effect of a Missed Role

Sheen also found a silver lining. Had he landed Born on the Fourth of July, he probably wouldn’t have done Major League, the 1989 sports comedy that became one of his signature hits. “I’m just pretty sure one would’ve gotten in the way of the other,” Sheen said. “And if it’s not true, that’s what I’m going with.”

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Emilio Estevez, wearing a green M65 field jacket, with his brother Charlie Sheen, wearing a Type A-2 leather flight jacket.

Thirty-five years later, Charlie Sheen isn’t bitter. He’s just telling it unfiltered, a little funny, and surprisingly gracious.

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