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 Milton Frome Guest Star Ray Hemphill Guest Star Ron Howard Guest Star Michael J. Pollard Guest Star Marjorie Bennett Guest Star Rod Amateau Producer, Director, Writer Ralph Murphy Director, Writer Berni Gould Writer Louella MacFarlane Writer Max Shulman Writer R. S. Allen Writer Fred S. Fox Writer Izzy Elinson Writer Joel Kane Writer Ed James Writer Mel Diamond Writer Ben Starr Writer Irving Elinson Writer John Kohn Writer Charles R. Marion Writer Jack Lloyd Writer