Max Shulman Creator 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 William Schallert Mr. Leander Pomfritt Actor Doris Packer Clarice Armitage, Mrs. Chatsworth Osborne Sr. Actor Steve Franken Chatsworth Osborne Jr. Actor Jean Byron Mrs. Ruth Adams, Dr. Burkhart Actor Richard Clair Lt. Merriweather Actor Raymond Bailey Dean Magruder Actor Bobby Diamond Duncan Gillis Actor Robert Paget Max Perkins 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 Rod Amateau Producer