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Although related to MGM head Louis B. Mayer, Cummings started his career at the studio as a low-paid office boy. He worked his way up to script supervisor and assistant director, and was eventually placed in charge of the studio's short-subjects department, where he personally produced most (and directed several) of them. In 1934 MGM made Cummings a producer of features, and as such he was responsible for many of the studio's most famous musicals.