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Oates first acted in a student play while attending the University of Louisville. He moved to New York in 1954, hoping to find work on the stage or TV; instead he had a series of odd jobs. Eventually he appeared in a few live TV dramas, and when this work slowed down he moved to Hollywood; there he became a stock villain in many TV and film Westerns. Over the years he gained respect as an excellent character actor; by the early '70s he was appearing in both unusual, unglamorous leads and significant supporting roles. His breakthrough role was in In the Heat of the Night (1967). He played the title role in Dillinger (1973).