Cast
- Dwayne Hickman as Dobie Gillis
- Frank Faylen as Herbert T. Gillis
- Florida Friebus as Winnifred "Winnie" Gillis
- Bob Denver as Maynard G. Krebs
- Tuesday Weld as Thalia Menninger
- Warren Beatty as Milton Armitage
- Sheila James Kuehl as Zelda Gilroy
- Steve Franken as Chatsworth Osborne, Jr. (credited as "Stephen Franken")
- Doris Packer as Mrs. Armitage and Mrs. Chatsworth Osborne, Sr.
- William Schallert as Professor Leander Pomfritt
- Joyce Van Patten as Mrs. Pomfritt
- Jean Byron as Dr. Imogene Burkhart and Mrs. Ruth Adams
- Bobby Diamond as cousin Duncan "Dunky" Gillis
- Darryl Hickman as brother Davey Gillis
- Michael J. Pollard as cousin Jerome Krebs
- Marjorie Bennett as Mrs. Kenny
- Raymond Bailey as Dean Magruder
- Clinton Sundberg as Trembley, the Armitage butler
- Dabbs Greer as Zelda's father
- Willis Bouchey as Maynard's father
- Herbert Anderson as Maynard's and Dobie's High School Teacher
Read more about this topic: The Many Loves Of Dobie Gillis
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“However, our fates at least are social. Our courses do not diverge; but as the web of destiny is woven it is fulled, and we are cast more and more into the centre. Men naturally, though feebly, seek this alliance, and their actions faintly foretell it.”
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