Sheen's film career began in 1984 with a role in the Cold War teen drama
Red Dawn with Patrick Swayze, C. Thomas Howell, Lea Thompson, and Jennifer Grey. Sheen and Grey reunited in a small scene in
Ferris Bueller's Day Off (1986), where he portrayed a drug dealer. He also appeared in an episode of the anthology series
Amazing Stories. Sheen had his first major role in the Vietnam War drama
Platoon (1986). In 1987, he starred with his father in
Wall Street. Both
Wall Street and
Platoon were directed by Oliver Stone. In 1988, Stone asked Sheen to star in his new film
Born on the Fourth of July (1989), but later cast Tom Cruise instead. Sheen was never notified by Stone, and only found out when he heard the news from his brother Emilio. Sheen did not take a lead role in Stone's subsequent films,
although he did have a cameo role in
Money Never Sleeps.
In 1987, Sheen was cast to portray Ron in the unreleased
Grizzly II: The Predator, the sequel to the 1976 low budget horror movie
Grizzly. In 1988, he starred in the baseball film
Eight Men Out as outfielder Happy Felsch. Also in 1988, he appeared opposite his brother Emilio in
Young Guns and again in 1990 in
Men at Work. In 1989, Sheen, John Fusco, Christopher Cain, Lou Diamond Phillips, Emilio Estévez and Kiefer Sutherland were honored with a Bronze Wrangler for their work on the film
Young Guns.
In 1990, he starred alongside his father in
Cadence as a rebellious inmate in a military stockade and with Clint Eastwood in the buddy cop action film
The Rookie.
The films were directed by Martin Sheen and Eastwood, respectively. In 1992, he starred in
Beyond the Law with Linda Fiorentino and Michael Madsen. In 1994, Sheen was awarded a star on the Hollywood Walk of Fame. In 1997, Sheen wrote his first movie,
Discovery Mars, a direct-to-video documentary revolving around the question, "Is There Life on Mars?". The next year, Sheen wrote, produced and starred in the action movie
No Code of Conduct.
Sheen appeared in several comedy roles, including the
Major League films,
Money Talks, and the spoof
Hot Shots! films. In 1999, Sheen appeared in a pilot for A&E Network, called
Sugar Hill, which wasn't picked up. In 1999, Sheen played himself in
Being John Malkovich. He also appeared in the spoof series
Scary Movie 3 and follow up
Scary Movie 4.
Sheen appears as Dex Dogtective in the unreleased Lionsgate animated comedy
Foodfight.