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Cast & Characters. Dwayne Hickman as Dobie Gillis. Frank Faylen as Herbert T. Gillis. Florida Friebus as Winnifred Winnie Gillis. Bob Denver as Maynard G. Krebs. Tuesday Weld as Thalia Menninger. Warren Beatty as Milton Armitage. Sheila James Kuehl as Zelda Gilroy.
Cast & Characters | Broadcast History | Theme Song | DVDs | Watch Episodes | Photos | Trivia | Comments. The Many Loves of Dobie Gillis is a sitcom that aired on CBS from 1959 to 1963 about a teenage boy named Dobie Gillis who cared about the only thing any teenage boy cares about ... teenage girls! He had one girl in particular that he particularly desired (played by Tuesday Weld) but so did two rich playboy teenagers (one of whom was played by a very young Warren Beatty!).