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At the age of 7, his father died, leaving his mother and her six children in poverty, of the children, 4 died in early years. To earn some money to support the family, Robert took odd jobs, before becoming a jockey. This career ended when the horse, Pink Star, the future Kentucky Derby winner of 1907, fell and broke Robert's leg. Robert then went to work as bellboy at the Hotel Sinton in Cincinnati, Ohio, where he came in contact with actors who saw possibilities for him on the stage as comic. He joined several vaudeville companies, touring not only North America, but also the British Empire. Around 1917, he married an eccentric dancer. In 1922, he appeared with W.C. Fields in "The Blue Kitten", and also wrote plays. He hit it big, when he was signed for Florenz Ziegfeld Jr.'s "Rio Rita" in 1927, where he teamed up with Bert Wheeler. Both repeated their stage roles in RKO's filmed version of that musical. Due to their success, both were teamed up again for more pictures, a career that kept on until failing health made further work impossible. Although Variety suggested that both should try as singles, the movies they made apart weren't successful. He died on October 31, 1938 of kidney disease.

Raquel Torres, Bert Wheeler, and Robert Woolsey in So This Is Africa (1933)

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Robert Woolsey

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