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 Steve Franken Chatsworth Osborne Jr. Actor Doris Packer Clarice Armitage, Mrs. Chatsworth Osborne Sr. Actor Robert Paget Max Perkins Actor Jean Byron Mrs. Ruth Adams, Dr. Burkhart Actor Raymond Bailey Dean Magruder Actor Bobby Diamond Duncan Gillis Actor