The son of Hannah Chaplin and music hall entertainer Leo Dryden and thus the half brother of Charles Chaplin and Sydney Chaplin, Wheeler Dryden was apparently estranged from his famous relatives from childhood. Dryden reportedly got in touch with brother Charlie in America through actress Edna Purviance and was offered a chance to star in his own Gray Seal comedy productions in New York in 1919. He later appeared in Stan Laurel's Mud and Sand (1922) and was the "other man" in an independently made melodrama False Women (1921). In 1928, he directed half brother Syd in A Little Bit of Fluff, filmed in England, and much later, functioned as Charlie's assistant director on his final Hollywood productions, The Great Dictator (1940) and Monsieur Verdoux (1947).