Emilio Estevez is central to Charlie Sheen’s retelling of how Born on the Fourth of July slipped away. In a new segment from In Depth with Graham Bensinger, Sheen says he believed Ron Kovic was his after meetings with Oliver Stone and a dinner with Kovic. Then Emilio Estevez called. As per the In Depth with Graham Bensinger Charlie Sheen podcast released on October 3o, 2025, Charlie Sheen said,
“Hey, man. You sitting down?" And I think somebody died, right? I'm like, "No, what's going on?" He says, "Uh," he says, "Cruz is doing Born on the Fourth." I love that Ailio thought that I need to be seated to get news he thought was going to make me faint.”
Sheen frames the moment as disappointment and “betrayal,” noting Stone had been enthusiastic and then went quiet. He adds that Emilio Estevez and Tom Cruise were close in those years and that Cruise had even been around the Estevez-Sheen household, with Emilio Estevez and Cruise having worked together on The Outsiders. Sheen still praised Cruise’s work and told Bensinger that losing Kovic cleared the path to shoot Major League in 1989. The Two and a Half Men actor kept perspective and moved on.
“You sitting?”: Emilio Estevez's phone call that told Sheen he’d lost Kovic to Cruise
Sheen lays out the beats plainly. As per In Depth with Graham Bensinger Charlie Sheen podcast, he stated,
“Hey, man. You sitting down?" And I think somebody died, right? I'm like, "No, what's going on?" He says, "Uh," he says, "Cruz is doing Born on the Fourth." I love that Ailio thought that I need to be seated to get news he thought was going to make me faint.”
Sheen says the initial shock gave way to realism and respect. Charlie Sheen remarked,
“It was also the betrayal factor of it, you know. Um, so I was like, "Okay, all right." You know, Oliver's been a fan of Tom's for a long time. Um, it's, you know, it's a different movie if Tom does it than if I do it.”
He added further,
"And I was like, you know, what are you going to do? Like, what? Uh, you can't lose something you never had."
Emilio Estevez sits at the center of the story throughout: he delivered the news, he had an early ties with Tom Cruise, and he shared early career overlap that made the call hit harder. Two lines of context underscore that link. Emilio Estevez and Cruise were friends from the early 1980s, and Cruise once stayed at the Estevez-Sheen home during those formative years. That proximity explains why Emilio Estevez was the one who called and why the moment still resonates for Sheen.
Inside the near-casting: meetings with Oliver Stone and Ron Kovic, then silence
Sheen describes a pre-production courtship that felt like a lock. He recounts multiple conversations with Oliver Stone and a dinner with Ron Kovic that convinced him he had the part. Then communication stopped. Sheen stated that he was told Stone was “in Cuba,” that weeks passed, and that he later heard Cruise was in. He also notes there was no contract, only a handshake, which made the reversal sting, stating,
"I didn't sign a contract. There was no, but I did. There was a handshake...we far enough down the road to feel like this was our next thing"
Aftermath: Cruise’s Oscar nod, Sheen’s Major League, and how the pivot shaped both careers
Tom Cruise’s performance in Born on the Fourth of July earned a Best Actor nomination and marked a milestone in his awards trajectory. Cruise’s nominated roles include Born on the Fourth of July, Jerry Maguire, and Magnolia, with later recognition as a producer on Top Gun: Maverick.
The Academy subsequently announced an honorary Oscar for Cruise, noting his decades of contributions. In the same Bensinger conversation, Sheen credits the near-miss with freeing his calendar to film Major League in 1989, which became one of his defining roles. Charlie Sheen said in the podcast,
“You should have won the freaking Oscar,”
praising Cruise while accepting how the timeline fell. The pivot is simple in Sheen’s telling: Emilio Estevez made the call, Cruise took Kovic, and Sheen shot Major League. Emilio Estevez, by circumstance and friendship, anchors the story’s turning point for both men. Estevez remains the thread that ties the loss, the phone call, and the eventual career outcome together. Emilio Estevez is, in effect, the witness who turned a rumor into a record.
Stay tuned for more updates.
American actors Emilio Estevez, wearing a green M65 field jacket, with his brother Charlie Sheen, wearing a Type A-2 leather flight jacket and Gold's Gym t-shirt, at the premiere of John Badham's 'Stakeout', 1987. (Photo by Vinnie Zuffante/Getty Images)