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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.
1 Gilligan (played by Bob Denver) - The title character of the show. 2  Gilligan is a crewman of the S. S. Minnow who worked for the Skipper.3  He is a bumbling idiot who always seems to mess up the castaways' escape.4  He wears a red shirt, light blue pants, and a white sailor's hat. Gilligan is a crewman of the S. S. Minnow who worked for the Skipper. 2  He is a bumbling idiot who always seems to mess up the castaways' escape. 3  He wears a red shirt, light blue pants, and a white sailor's hat. 4  In the never-aired pilot episode, it is revealed that his first name is Willy.