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A stage actor in the 1900s, Cummings began acting in films in 1909. He appeared in such notable films as Cecil B. De Mille's Don't Change Your Husband and the comedy The Saphead with Buster Keaton. Cummings switched to directing in the early '20s and helmed numerous silent dramas and actioners. In the '30s and '40s he showed a special flair for musicals, guiding such beloved performers as Shirley Temple (Curly Top, Poor Little Rich Girl, Little Miss Broadway, Just Around the Corner), Alice Faye (Hollywood Cavalcade, Lillian Russell, That Night in Rio), and Betty Grable (Down Argentine Way, Springtime in the Rockies, Sweet Rosie O'Grady, The Dolly Sisters). Cummings' other notable talkies include the Cisco Kid western In Old Arizona, which he co-directed with Raoul Wals; the Irving Berlin musical Louisiana Purchase starring Bob Hope; and the Paul Dresser biopic My Gal Sal starring Rita Hayworth.