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Years before CBS shut down Two and a Half Men, Charlie Sheen was a bona fide star -- what went wrong?

Shaun Harrison
1 of 17 MGM UA/ Kobal Collection

Matt Eckert in Red Dawn (1984)

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.
2 of 17 20th Century Fox/Everett Collection

Cappie in Lucas (1986)

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.
3 of 17 Paramount Pictures

Boy in Police Station in Ferris Bueller's Day Off(1986)

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!
4 of 17 Orion/Kobal Collection

Chris Taylor in Platoon (1986)

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.
5 of 17 20th Century Fox

Bud Fox in Wall Street (1987)

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.
6 of 17 20th Century Fox/Kobal Collection

Dick Brewer in Young Guns (1988)

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.
7 of 17 Orion/Kobal Collection

Hap Felsch in Eight Men Out (1988)

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.
8 of 17 Morgan Creek/Paramount/Kobal Collection

Ricky Vaughn in Major League (1989)

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.
9 of 17 Epic/Euphoria/Kobal Collection

Carl Taylor in Men at Work (1990)

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.
10 of 17 Waner Bros./Kobal Collection

David Ackerman in The Rookie (1990)

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.
11 of 17 20th Century Fox/Kobal Collection


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.
12 of 17 Walt Disney/Kobal Collection

Aramis in Three Musketeers (1993)

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.
13 of 17 Fotos International/Getty Images

Ryan in Friends (1996)

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.
14 of 17 USA Films

Charlie Sheen in Being John Malkovich (1999)

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.
15 of 17 Everett Collection

Artie Mitchell in Rated X (2000)

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.
16 of 17 ABC Archive/Getty Images

Charlie Crawford in Spin City (2000-2002)

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).
17 of 17 Greg Gayne/Warner Bros.

Charlie Harper in Two and a Half Men (2003-2011)

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.