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 Joel Crothers Guest Star Milton Frome Guest Star Robert Paget Max Perkins Guest Star Romney Tree Guest Star James Yagi Guest Star Rod Amateau Producer Ralph Murphy Director Fred S. Fox Writer Irving Elinson Writer