Montgomery, on stage by his teens, was scouted by MGM. The studio changed his name to Kent Douglass and cast him in dashing or romantic roles opposite some of MGM's powerhouse actresses, such as Joan Crawford (in Paid (1930) ) and Katharine Hepburn (in Little Women (1933), in which he played the role of Laurie).Just as he was gaining ground, MGM inexplicably changed his name again, to Douglass Montgomery, and lent him to other studios. Although he forged ahead with The Mystery of Edwin Drood (1935), Harmony Lane (1935) (in which he portrayed composer Stephen "Suwanee River" Foster), and Bob Hope's comedy classic The Cat and the Canary (1939), his career was in decline by WWII. He enlisted with the Canadian infantry and served for four years. Montgomery returned to acting but was scarcely noticed. He starred in a few routine British films, then returned to the US for a few more and for some work in television. He died in 1966.