In John Milius' 1984 film about the dawn of a third world war, Sheen plays one of two teenage brothers (the other played by Patrick Swayze) who resist an invasion by the Soviet Union and its Latin American allies.

Sheen plays a popular high school football player who befriends scrawny geek Lucas (Corey Haim), a kid he used to bully. Difficulties arise when Cappie becomes a good guy and starts seeing Maggie (Kerri Green), the girl Lucas has a crush on.

Did Sheen even have dialogue? We just remember him looking dazed while sizing up Jeannie (Jennifer Grey) – and then all of a sudden they're making out!

In Oliver Stone's Oscar-winning Vietnam War-era classic, Sheen plays a naive American who drops out of college and volunteers for combat. He's quickly disillusioned -- both with the conflict with the enemy and with the men in his platoon. The film is Sheen's most successful to-date.

Ah yes, '80s excess. Sheen earned rave reviews for his portrayal of a young stockbroker desperate to succeed, who gets tangled up in the affairs of corrupt corporate raider Gordon Gekko (Michael Douglas). Real-life father Martin Sheen played his dad in the film.

Sheen joins his brother Emilio Estevez as one of six young gunman who've been deputized to catch the murderer of an English cattle rancher. These self-styled "Regulators" get out of hand thanks to the hot-headed Billy the Kid (Estevez), and soon they find they're the ones on the run.

In John Sayles' film about one of the biggest scandals in Major League Baseball history, Sheen plays an outfielder who, along with other Chicago White Sox players, conspired with gamblers to throw the World Series in 1919.

In this baseball comedy, Sheen is a pitcher with a prison record who gets a second chance when he's hired by the new owner of the Cleveland Indians. Too bad she doesn't want to succeed, filling the team with the worst possible players.

Carl and James (brother Emilio Estevez, who also wrote and directed the film) are a pair of troublemaking garbagemen who accidentally get caught up in the murder of a guy they coincidentally had shot earlier in the butt with a pellet gun. The comedy didn't do so well with critics or audiences.

Clint Eastwood plays veteran cop Nick Pulovski who recently lost his partner while investigating a German crime lord Strom. Sheen plays his new partner, a recently promoted detective, and together attempt to take down Strom.

Lt. Sean "Topper" Harley, Rhett Butler and Superman in Hot Shots! (1991) In the Top Gun spoof, Sheen plays the Tom Cruise type, a psychologically imbalanced fighter pilot tasked with destroying Saddam Hussein's nuclear plants. It's one of his most successful films.

In this swashbuckling adventure, Sheen plays one of the titular swordsmen alongside Kiefer Sutherland and Oliver Platt. After they've disbanded, they rejoin to help aspiring Musketeer D'Artagnan stop Cardinal Richelieu's nefarious plot to form an alliance with enemy England.

In the episode, titled "The One with the Chicken Pox," Sheen plays an old flame of Phoebe's who arrives into town just as she's caught the chicken pox. The two spend the episode trying not to scratch.

The trippy fantasy from the mind of writer Charlie Kaufman and director Spike Jonze stars John Cusack as a puppeteer who discovers a portal leading into actor John Malkovich. When Malkovich catches wind that something's amiss he consults his friend Sheen -- spoofing himself -- before seeking out the portal himself.

The Showtime movie chronicles the story of the Mitchell brothers Artie and Jim (brother Emilio Estevez, who also directed), notorious porn pioneers in San Francisco during the the 1970s and 1980s.

Sheen joined the sitcom in its fifth season – and earned a Golden Globe award for his work -- following the exit of Michael J. Fox. As the new Deputy Mayor, Charlie had to deal with the good-hearted but bumbling Mayor (Barry Bostwick) and campaign manager Caitlin (Heather Locklear).

Sheen is the hedonistic womanizer whose life is interrupted when his brother and young nephew move into his beach-front house. His work on the show earns him a pretty $1.8 million per episode and he’s received four Emmy nominations for the role.