Born in New York City, New York to a well-to-do family, Alan Crosland attended from Dartmouth College. After graduation he took a job as a writer with the New York Globe magazine. Interested in the theatre, he began acting on stage, appearing in several ptroductions with Shakespearian actress Annie Russell (1864-1936).

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 untimely death in September of that year.

In 1925 Crosland was working for Jesse L. Lasky's Famous Players-Lasky Company when he was hired by Warner Bros. to work at their Hollywood studios. He had directed several silent films for Warner, including two with leading star John Barrymore, when he was chosen to direct Al Jolson in 1927's The Jazz Singer. The film would make him famous as the first of the new talkies that changed the course of motion pictures.

Alan 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.

His son, Alan Crosland, Jr. (1918-2001) would also have a successful career as a film director.