He began his career in Hollywood at MGM in 1930, playing the second male lead in films such as "Paid" and "Five and Dime". When he signed his contract at the studio his name was changed to Kent Douglass, to avoid confusion with that studio's star Robert Montgomery. Upon leaving MGM in 1932, he changed it back to Douglass Montgomery.
Among his most celebrated roles was Laurie in Little Women (1933), opposite Katharine Hepburn's Jo March. He also played Johnny Hollis ("Johnny-in-the-Clouds") in The Way to the Stars (1945).
In 1934, Montgomery was the victim of a murder attempt.
Montgomery married British Actress Kay Young (born Kathleen Tamar Young) on March 14, 1952 at Bethlehem Federated Church. He was her second husband. Young had divorced film actor Michael Wilding the year before she wed Montgomery. (Wilding remarried in 1952, to Hollywood star Elizabeth Taylor.) Young and Montgomery remained married until his death.
Douglass Montgomery died of spinal cancer in Norwalk, Connecticut, aged 58, on July 23, 1966. He was cremated, with his ashes given to his widow.
