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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.
Gilligan may have been his signature role, but when he took the part in 1964 Denver was already widely known to TV audiences for another iconic character, Maynard G. Krebs, the bearded beatnik friend of Dwayne Hickman's Dobie in the ''The Many Loves of Dobie Gillis,'' which aired on CBS from 1959 to 1963.