Charlie Sheen has endured one of the wildest rollercoaster careers in the history of Hollywood. The son of screen idol Martin Sheen began his career with the 1984 Cold War thriller Red Dawn before appearing in some of the most iconic movies of the decade. In 1986, Sheen starred in Oliver Stone's Best Picture-winning Platoon, hailed as one of the greatest Vietnam War movies ever made.
Sheen continued to work steadily throughout the 90s and 2000s, transitioning to television when he was cast in the political sitcom Spin City. His more recent hits include Two and a Half Men and Anger Management until 2014.
Hot Shots! Part Deux (1993) 57%
In Jim Abraham's Hot Shots! Part Deux, the satirical aim at Top Gun in the first film is targeted on the shoot-em-up Rambo movies instead. Sheen reprises his role as Topper Harley, macho American hero extraordinaire.
When the CIA sets out to locate the last rescue team who've lost communication in Iraq, the agency recruits Harley out of a peaceful monastery to do battle with the enemy. President Tug Benson (Lloyd Bridges) gives Harley direct orders in a bald spoof of every over-the-top 80s action movie.
The Arrival (1996) 64%
One of the last favorably-reviewed movies of Sheen's career includes The Arrival, a sci-fi/thriller in which a brilliant young astronaut discovers a malicious alien life form.
Written and directed by David Twohy, the story concerns Zane Zaminsky (Sheen), an unassuming astronaut who discovers a radio signal emanating from an extraterrestrial life form. When reporting the signal to his superiors, Zane is fired, leading to his own investigation of the truth that stirs up a slew of conspiracy theories. As Zane races to uncover the lethal secret harbored by the aliens, his life and those around him are placed in grave danger.
Lucas (1986) 70%
The coming-of-age sports-movie Lucas stars the late Corey Haim as the titular teenager with a big brain and even larger heart. After the physically slight and nerdy young boy from the wrong side of the tracks enjoys a splendid summer with new girl Maggie (Kerri Green), he must contend with her much more popular suitor, Cappie (Sheen).
Cappie is the quarterback and captain of the high-school football team Lucas and Maggie attend. In an attempt to win Maggie over, Lucas joins the football team despite being far too small to make the squad. In the end, Lucas risks his life to express his love.
Wall Street (1987) 78%
A year after starring in Platoon, Oliver Stone cast Sheen to star in Wall Street, a tale of 80s excess and corporate greed. Sheen's costar Michael Douglas won an Oscar for Best Performance by a Male in a Leading Role.
Sheen plays Bud Fox, a bright-eyed stockbroker with the express goal of becoming rich. When Fox works his way up and catches the attention of powerful corporate raider Gordon Gecko (Douglas), his scruples quickly evaporate. Willing to do whatever it takes to succeed, Fox begins bending the law and operating on inside trading info that threatens his father Carl's (Martin Sheen) lasting legacy.
Ferris Bueller's Day Off (1986) 80%
Sheen all but steals the show during his lone scene in John Hughes's classic 80s teen comedy, Ferris Bueller's Day Off. Credited as "Boy in the Police Station," Sheen plays a hardened-criminal who first insults and then makes out with Ferris' irate sister Genie (Jennifer Grey).
The larger plot follows Ferris (Matthew Broderick), a charming teenager who plans the ultimate day off on a sunny spring day in Chicago. Along with his closest friend Cameron (Alan Ruck) and girlfriend Sloan (Mia Sara), Ferris visits a museum, baseball game, musical parade, five-star restaurant, and more all before the sun goes down.
Hot Shots! (1991) 83%
Pete "Maverick" Mitchell (Tom Cruise) is the target of overt lampoonery in Hot Shots!, a Mel Brooks-style sendup in which Sheen takes center stage as Top Gun-like fighter pilot Topper Harley.
When Harley is dispatched to join the SS Essess, he's given a mission to destroy Sadam Hussein's nuclear armaments. However, Topper's fragile mental state and inability to live up to his father Buzz Harley's (Bill Irwin) legacy. Sheen's Two and a Half Men costar Jon Cryer appears in the film as well.
Major League (1989) 83%
One of Sheen's most iconic cinematic roles includes that of Ricky Vaughn, the hot-tempered, poor-sighted, and strong-armed strikeout specialist in the baseball classic Major League.
The film follows the rag-tag members of the Cleveland Indians baseball team, whose nefarious new owner plans to deliberately lose as many games as possible in order to relocate the franchise to another city. Under the leadership of journeyman catcher Jake Taylor (Tom Berenger), the team does the exact opposite en route to reaching the championship game.
Eight Men Out (1988) 86%
In his second baseball movie in as many years, Sheen joined the star-studded ensemble of Eight Men Out, John Sayles' depiction of the infamous 1919 Black Sox scandal.
The scandal includes various Chicago White Sox players who accepted illegal bribes in exchange for deliberately losing the 1919 World Series. Sheen joins John Cusack, Michael Rooker, Christopher Lloyd, John Mahoney, David Strathairn, and more.
Platoon (1986) 88%
Oliver Stone's Platoon, based on his own experiences in the Vietnam War, was named Best Picture by the Academy Awards in 1987. In addition to the critical success, the movie turned a $6-million budget into a $138 million global hit.
Much like his father Martin Sheen did in Apocalypse Now seven years earlier, Charlie stars Chris Taylor, a typical American everyman whose eyes the audience witnesses the story through. As Chris forms a close camaraderie with his fellow soldiers, he learns the horrors of war and the life-lessons that come along with losing loved ones in a heated battle.
Being John Malkovich (1999) 93%
Much like he did in Ferris Bueller's Day Off, Sheen nearly steals the show in his lone scene in Being John Malkovich, Spike Jonze's trippy existential comedy.
Scripted by Charlie Kaufman, the bizarre plot follows a timid puppeteer Craig Schwartz (John Cusack), who accidentally stumbles on a portal that allows access to the mind of acclaimed actor John Malkovich. When Malkovich catches wind that something awry is happening, he confides in his friend Charlie Sheen (playing himself), who offers very few words of encouragement. The film scored three Oscar nominations, including Best Director (Jonze) and Original Screenplay (Kaufman).