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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.
Main characters (the castaways) Gilligan (played by Bob Denver) - The title character of the show. Gilligan is a crewman of the S. S. Minnow who worked for the Skipper. He is well-meaning but bumbling, and he always seems to inadvertently mess up the castaways' escape.