A somewhat lackadaisical student, Sheen was expelled from Santa Monica High School a few weeks shy of receiving his diploma. He focused instead on his desire to act, seeking out and landing a role in the never-released horror film Grizzly II:
The Predator (1984). Later that year, Sheen made his adult cinematic debut in the Soviet invasion thriller Red Dawn.
After a handful of TV movies, Charlie Sheen landed the breakthrough role of his career in Oliver Stone’s autobiographical war drama Platoon (1986).
He earned kudos for his brutally realistic portrayal of a young soldier's tour of duty in Vietnam, while the film won four Oscars, including Best Picture.
The following year, Sheen costarred in Stone’s Wall Street as the ruthless protégé Bud Fox, who is seduced by the wealth and power of corporate raider Gordon Gekko (played by Michael Douglas).
As part of an ensemble that included John Cusack, Christopher Lloyd, and D.B. Sweeney, Sheen gave a notable performance in John Sayles’ gripping account of the 1919 “Black Sox” baseball scandal Eight Men Out (1988). After starring in the 1990 action films Navy SEALS and
The Rookie, he showcased his flair for comedy in the mindlessly entertaining spoof Hot Shots (1991). In 1993, Sheen reprised his role as maverick air force pilot Topper Harley in the equally successful sequel Hot Shots! Part Deux.
In the late 1990s, Charlie Sheen formed a production company with Brett Michaels (former lead singer of the heavy metal band Poison). Directed by Michaels and starring Sheen, the two collaborated on the TV film No Code of Conduct (1998). In 2000, Sheen and his brother Emilio headlined the controversial biopic Rated X. Based on the life of porn industry pioneers Jim and Artie Mitchell, the film was screened at the Sundance Film Festival and later premiered on cable TV’s Showtime Network. Also in 2000, Sheen replaced Michael J. Fox as deputy mayor on the hit sitcom Spin City. In 2003, he starred in the panned horror spoof Scary Movie 3 for director David Zucker. Sheen is currently starring as beleaguered bachelor Charlie Harper on the CBS sitcom Two and a Half Men.
Notorious for his recurrent battles with drugs and alcohol, Sheen was again the subject of negative publicity when he served as the star witness in the 1995 trial of Hollywood madam Heidi Fleiss. He confessed to spending an excess of $50,000 to purchase sexual services from 27 different prostitutes. The following year, Sheen was arrested and charged with the assault of former girlfriend Brittany Ashland. Pleading no contest to the battery, he received a suspended sentence and two years of probation.