Entertainment Movies 15 Iconic Roles That Made Charlie Sheen Famous From Red Dawn to Anger Management and beyond, look at some of the best roles the actor has played throughout his storied career By Drew Mackie Published on November 16, 2015 02:45 PM Share Tweet Pin Email Photo: Getty Born Carlos Irwin Estevez, the man now best known as Charlie Sheen adopted the surname of his famous actor dad, Martin Sheen, and went on to become a celebrated actor in his own right. (Show business, after all, is a Sheen-Estevez family tradition.) Over the course of his career, Sheen has become known for scandals and his volatile personal life in addition to acting. In the wake of recent news that Sheen is allegedly HIV positive, many fans are wishing him courage, health and resilience. In respect to over four decades of Sheen’s work in Hollywood, we’re focusing on the roles that made him famous in the first place. (Warning: Some of these clips contain NSFW language.) 1. Red Dawn (1984) In his first major role, Sheen plays one of the teens who literally go commando and attempt to fend off an invading army force. You might remember it as just an action movie, but in this scene in particular – in which Sheen and Patrick Swayze’s characters meet their father (Harry Dean Stanton) in an internment camp – a teary-eyed Sheen shows off some of the acting chops that would later win him roles. 2. Lucas (1986) Sheen plays Cappie, jock with a heart of gold who ended up vying for the affections of the new girl in town (Kerri Green) against the title character (Corey Haim), and you wouldn’t be faulted for rooting for Cappie instead of Lucas. 3. Ferris Bueller’s Day Off (1986) Sheen doesn’t need a big role to be memorable. He’s only in the film briefly, playing the juvenile delinquent who kisses Ferris’ little sister (Jennifer Grey), but he probably left more than a few audience members asking “Hey, who played that bad boy?” when they left the theater. 4. Platoon (1986) Easily the biggest role of Sheen’s career at that point, he plays a solider in the Vietnam War. The Oliver Stone film picked up the Best Picture Oscar, among others, and a handful of nominations, but Sheen performance wasn’t nominated. It should have been. He was robbed. Charlie Sheen’s Changing Looks! 5. Wall Street (1987) Michael Douglas rightly won the Best Actor Oscar for his turn as Gordon Gecko, and it’s mostly his character’s lines that people remember from the film today. Sheen, who was not nominated, did good work as the film’s core character, however. Wall Street follows Bud Fox’s journey, and Sheen has you rooting for the character. He deserved at least a nomination. 6. Young Guns (1988) Things to note: Sheen has great onscreen chemistry with his real-life brother, Emilio Estevez, and he knows how to die in style. 7. Major League (1989) If you haven’t seen Major League lately – or, you know, ever – it’s actually a very solid sports movie. It’s funny. It will have you rooting for the main characters even if you don’t usually care about baseball. And Sheen gets to show off a comic flair that he didn’t in his previous hits. In the end, it turns out poor eyesight is throwing off his character’s pitching game, and he gets glasses. It turns out young Charlie Sheen doesn’t look bad in spectacles. 8. Men at Work (1990) Again, seeing Charlie Sheen and Emilio Estevez onscreen together is a treat, and the fact that Estevez directed Men at Work and cast Sheen as his co-lead makes this low-budget comedy even better. 9. Hot Shots! (1991) Top Gun was begging for a parody, and Sheen ended up being the right guy to send up Tom Cruise’s role. While Sheen can totally do drama, there’s something about seeing him do comedy that makes you think he might be in his natural element. In this scene, Sheen and Valeria Golino take their best stab at what Leslie Nielsen and Priscilla Presley did in The Naked Gun, and it works. 10. Friends (1996) Quite a few celebs guest-starred on Friends, but in counting off Sheen’s most memorable roles, you have acknowledge the strangeness of watching Sheen engage in some chicken pox-spreading lovemaking with Lisa Kudrow. Hurray for stunt casting! 11. Being John Malkovich (1999) There’s no shortage of weirdness in this genre-defying Spike Jonze movie, but one of the weirdest parts has to be its depiction of a world in which John Malkovich is buddies with Charlie Sheen. We’d like to think they hang out in real life, and even in a small role in a very strange movie, we’d like to think people watching it for the first time said, “Whoa, how weird was it that Charlie Sheen was playing himself?” 12. Spin City (2000-2002) It’s hard to follow in Michael J. Fox’s footsteps, but we can’t forget that Sheen had a good two-season run on Spin City that set him up for even greater sitcom stardom 13. Two and a Half Men (2003-2011) Even if Sheen bowed out for the show’s final 80-something episodes, he still played Charlie Harper in a staggering 177 of them on the hit CBS sitcom. This may actually be his best-known role to date. His character may be the most famous in all of sitcom-dom to be killed by a falling piano. 14. Anger Management (2012-2014) This FX series probably had Sheen playing the closest role yet to his real-life persona, and we cannot forget that it was also the TV show that had him romancing his Scary Movie 5 costar, Lindsay Lohan, who played herself – just for one episode, but still. Oh, to hear the conversations they had on set. 15. Machete Kills (2013) Five words: “Charlie Sheen plays the president.” And the fact that his character’s name was President Rathcock makes it all the better.