Charlie Sheen is back in the public eye, hopefully for better reasons than his last few turns in the spotlight. After years of addiction issues, misguided press appearances, low-rent movies, sitcom firings, and other acts of self-destruction, Sheen is apparently clean, sober, and ready to talk about his past, with a memoir and a Netflix documentary (aka Charlie Sheen) both due out this week looking back on his life and career.

Sheen has been famous for so many other things for so long that it may not spring immediately to mind that he was once an in-demand movie star. At first, sitcoms were a smart pivot from a waning leading-man career: first replacing Michael J. Fox on the later seasons of Spin City, and then jumping to his own show with Jon Cryer, the long-running Two and a Half Men. Eventually, his TV career was consumed by his personal issues, with the FX sitcom Anger Management looking particularly like an enabling scheme. But when Sheen first became a star in the mid-to-late 1980s, he looked like a poster boy for the decade, particularly through two consecutive collaborations with Oliver Stone: the Oscar-winning films Platoon (Best Picture and Best Director for 1986) and Wall Street (Best Actor for 1987).

It wasn’t Sheen who won that leading-actor Oscar for Wall Street, of course; that was Michael Douglas, as the famously slick financier Gordon Gekko, opposite Sheen’s hungry young stockbroker Bud Fox. Sheen wasn’t nominated for Platoon, either; co-stars Tom Berenger and Willem Dafoe were both up for Best Supporting Actor. But in both movies, Stone uses Sheen as a crucial audience point-of-view surrogate; he’s our entry point into both stories. In Platoon, his Chris Taylor volunteers for the Vietnam War out of a misguided sense of patriotism, and the war disabuses him of the notion that his trust will be honored. His Bud Fox is not so idealistic as he attempts to climb the finance ladder, but he at least attempts to do things the “right” way (and fails, prompting Gekko to urge him back towards insider trading).

In retrospect, it feels a little odd that Charlie Sheen, of all people, repeatedly played a guy who puts his trust in American institutions, only to become disillusioned when they falter around him. He’s the son of a movie star, with bad-boy good looks and an almost cartoonish form of charisma. Emphasis on cartoonish: In the parody films that sustained his movie career in the 1990s and early 2000s, Sheen was spoofing a kind of stoic lone-wolf faith in himself and, paradoxically, his country – a man of action who sees American values as an extension of himself. But then, maybe that’s part of his Platoon and Wall Street characters, too, even if they’re not dangerous slicksters on their own. They don’t seem to consider that the military or financial conflicts they encounter might not favor his perception of the good guys.

In other words, the characters are stand-ins for Oliver Stone, who based Platoon on his own memories of the Vietnam War, which he also volunteered to fight in, just like Chris Taylor. Wall Street is somewhat less personal, in that Stone himself never worked in finance – but his father did, and of course Gekko is a corrupted father figure to Bud. Sheen isn’t much like Stone in his look or mannerisms; there’s probably a reason that he subsequently gravitated toward more mischievous roles. But then, Stone also became more of a provocateur while Sheen was off alternating successful comedies (Major League; Hot Shots!) with junkier action (Terminal Velocity; The Chase). There’s no young semi-idealist figure in Natural Born Killers or Nixon (and the Kevin Costner character in JFK is, well, less youthful, more Costner-y). Come to think of it, though, Sheen might have been a better fit for the desert noir of U-Turn than his old pal Sean Penn.

Stone and Sheen didn’t exactly remain on parallel paths; Sheen’s substance abuse eventually obliterated any chance of tracing a neat or unexpected career arc through his art, rather than his personal life. But he and Stone did share a tendency to sound increasingly off-reservation as they got older, with Sheen more explicitly suffering from addictions – something that has also plagued Stone, but seemingly more in his younger years. Sometimes, they seem to be floating in a similarly off-kilter orbit. They’ve both, oddly, dabbled in antivaccination conspiracies, Sheen during his marriage to Denise Richards and Stone by voting for Robert F. Kennedy Jr. during the most recent presidential election. Sheen’s last film to date, in fact, was an absolutely World Trade Center-set chamber drama called 9/11, basically a poor relation to Sheen’s 2006 film World Trade Center.

Sheen has no immediate plans to get back into acting, he’s recently said – particularly dramatic acting, which he sensibly speculates would take some time to get back into, compared to the more practiced rhythms of a sitcom. Honestly, it’s hard to picture what that would look like; his best work is so closely tied to Stone’s ’80s peak, which in turn is so different from movies as they’re made today. That, too, is weirdly in keeping with those Stone movies. Chris Taylor doesn’t seem like he becomes a career soldier. According to Wall Street: Money Never Sleeps, Bud Fox went back into business after doing some time for his financial crimes, but subsequently quit while he was ahead. (The sequel’s not about him, in any event.) Sheen’s battles may have been more self-inflicted and one-sided than the systemic screw-ups of Chris or Bud, but it does seem like he’s belatedly followed them through the trenches, and hopefully, finally ready to come out the other side.

Jesse Hassenger (@rockmarooned) is a writer living in Brooklyn. He’s a regular contributor to The A.V. Club, Polygon, and The Week, among others. He podcasts at www.sportsalcohol.com, too.