Crosland began his career in the motion picture industry in 1912 at Edison Studios in The Bronx, New York, where he worked at various jobs for two years until he had learned the business sufficiently well to begin directing short films. By 1917, he was directing feature-length films and in 1920 directed Olive Thomas in The Flapper, one of her final films before her death in September of that year.

In 1925, Crosland was working for Jesse L. Lasky’s film production company Famous Players-Lasky (later Paramount Pictures) when he was hired by Warner Bros. to work at their Hollywood studios. He had directed several silent films for Warner’s including directing Don Juan starring John Barrymore in 1926. It was the first feature-length film with synchronized Vitaphone sound effects and musical soundtrack, though it has no spoken dialogue. He was chosen to direct Al Jolson in The Jazz Singer (1927). The film would make him famous as the first of the new talkies that changed the course of motion pictures.

Crosland died in 1936 at the age of 41 as a result of an automobile accident on Sunset Boulevard in Los Angeles. He is interred in the Hollywood Forever Cemetery. His grave remained unmarked for 67 years until a headstone was donated by The Hollywood Underground in 2003.