Dwayne Hickman Dobie Gillis Actor Bob Denver Maynard G. Krebs Actor Yvonne Lime Melissa Frome Actor Tuesday Weld Thalia Menninger Actor Warren Beatty Milton Armitage Actor Jean Byron Mrs. Ruth Adams, Dr. Burkhart Actor Frank Faylen Herbert T. Gillis Actor Florida Friebus Winnie Gillis Actor Sheila Kuehl Zelda Gilroy Actor Tommy Farrell Riff Ryan Actor Darryl Hickman Davey Gillis Actor William Schallert Mr. Leander Pomfritt Actor Doris Packer Clarice Armitage, Mrs. Chatsworth Osborne Sr. Actor James Yagi Guest Star Angelo De Meo Guest Star Ray Hemphill Guest Star Michael J. Pollard Guest Star Marlo Thomas Guest Star Ryan O'Neal Guest Star Rod Amateau Producer