Sheen started acting in 1974 at the age of nine, appearing in a small role alongside his father in the television movie The Execution of Private Slovik. Sheen's film career began in 1984 with minor and supporting roles in films such as Red Dawn (1984) and Ferris Bueller's Day Off (1986). He also appeared in an episode of the popular anthology series Amazing Stories. In 1986 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, but when, in 1988, Stone approached Sheen about starring in his new film Born on the Fourth of July (1989) and Sheen was re-cast by Tom Cruise and wasn't notified by Stone himself, but ended up hearing the news from his brother Emilio Estevez, Sheen refused to work with Stone again.

In 1987, Sheen was cast to portray Ron in Grizzly II: The Predator, the sequel to the populair 1976 low budget horror movie Grizzly. But due to