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.