Dwayne Hickman Dobie Gillis Actor Bob Denver Maynard G. Krebs Actor Frank Faylen Herbert T. Gillis Actor Florida Friebus Winnie Gillis Actor Sheila Kuehl Zelda Gilroy Actor Tuesday Weld Thalia Menninger Actor Warren Beatty Milton Armitage Actor Tommy Farrell Riff Ryan Actor Yvonne Lime Melissa Frome Actor Darryl Hickman Davey Gillis Actor William Schallert Mr. Leander Pomfritt Actor Doris Packer Clarice Armitage, Mrs. Chatsworth Osborne Sr. Actor Jean Byron Mrs. Ruth Adams, Dr. Burkhart Actor James Yagi Guest Star Angelo De Meo Guest Star Ray Hemphill Guest Star Michael J. Pollard Guest Star Rod Amateau Producer, Director Max Shulman Writer