Recurring casting notes
Experienced child actress Tuesday Weld was cast as Dobie's love interest in "Caper at the Bijou" and stayed on as a semiregular. Weld and Dwayne Hickman had previously appeared as a teenaged couple in the 1958 Fox feature film Rally 'Round the Flag, Boys!, based on a Max Shulman novel, though produced without his input. Neither Hickman nor Weld was fond of the other, with Hickman later stating he felt Weld was not as dedicated as necessary to rehearsal and referring to her as "a pain in the neck". Weld reportedly found Hickman pushy and out-of-touch. Aged 15 at the time of shooting the pilot, Weld had to legally spend much of her time on set in school with a tutor, and the production periodically ran into issues involving Weld's later publicly known difficult home life.[13]
Her work in Dobie Gillis and the feature film The Five Pennies made Weld a star, leading to substantial publicity. She departed the series after the first year to star in features, although she was persuaded by Max Shulman to return for two guest appearances, "Birth of a Salesman" (season three, episode 21) and "What's a Little Murder Between Friends?" (season four, episode two).
Herbert Anderson was cast as Mr. Pomfritt, Dobie and Maynard's English teacher at school. Anderson appeared in a lead role in the pilot for Dennis the Menace; when that show was picked up (also by CBS), he chose to stay with that cast, and actor William Schallert appeared in the recurring role of Mr. Pomfritt through the end of season three.
Warren Beatty was cast as Milton Armitage, a recurring rival of Dobie's at his high school, during the first half of season one. Hickman later recalled that Beatty "looked at me like I was a bug" while on set. Beatty did remain friends with his brief co-star Michael J. Pollard. The two co-starred in Bonnie and Clyde eight years later. He quit the series in September 1959, midway through production of the first season after filming his fifth and final Dobie episode, "The Smoke-Filled Room", to appear in A Loss of Roses on Broadway.[14]
Former child actress Sheila James, who, playing daughter "Jackie" on The Stu Erwin Show, had worked with Dwayne Hickman on that series and The Bob Cummings Show, was cast without an audition as Zelda Gilroy, the tomboyish brainy girl who was in love with Dobie. Originally intended as a one-shot character for the episode "Love is a Science" (season one, episode three), Max Shulman liked both Zelda and Sheila James and had Zelda retained as a semiregular character. Signing a contract with Dobie Gillis necessitated James, then an 18-year-old college student, changing her major from theater to English, so Shulman could assist her with her studies on set.
After the third season of Dobie Gillis, Rod Amateau and Max Shulman produced a pilot for a Zelda spinoff starring Sheila James as Zelda Gilroy, with Joe Flynn and Jean Byron cast as her parents.[15] However, CBS president James Aubrey lingered over moving forward with the Zelda series for a long time before firmly rejecting the series, with Amateau telling James in private that Aubrey had found Zelda (and by extension James, then a closeted lesbian) "too butch".[13] James' contract for the pilot and the resulting waiting period caused her to be absent from much of the fourth and final season of Dobie Gillis, though Amateau was able to hire her to return as Zelda for four episodes towards the end of the season.[15] Acting roles became sparse for James by the late 1960s; she went into law and politics under her birth name of Sheila Kuehl, and later became the first openly gay person elected to the California State Legislature.[13]
Steve Franken, a 28-year-old character actor, was cast immediately after Beatty's departure as Chatsworth Osbourne, Jr., a replacement character for Milton Armitage. While both Milton and Chatsworth were rich rivals of Dobie Gillis's (and both characters shared the same actress, Doris Packer, for a mother) and were, according to canon, cousins, where Beatty's Milton was a menacing and athletic physical threat, Franken's pompous, foppish Chatsworth tended to plot and scheme his way through competitions with Dobie, more often than not using his riches to get ahead.[6] The Chatsworth character became popular enough that the producers had to consciously limit his appearances on the series to roughly one per month to prevent Franken from upstaging Hickman and Denver, but Franken stated both during and after Dobie Gillis that playing Chatsworth led him to be typecast and stifled his career.[6]
Young actor Bobby Diamond was brought on at the beginning of season four as Dobie's teenaged cousin, Duncan "Dunky" Gillis. By 1962, the 28-year-old Dwayne Hickman had begun to look too mature to carry the teenager-based plot lines, and instead Diamond's "Dunky" was given this material, with the older yet immature Maynard as a running partner. The character was dropped midway through the fourth season, with attention shifting back to the characters of Dobie, Maynard, Chatsworth, and Zelda for the remaining episodes of the series.
Actresses who played Dobie's love interests included Cheryl Holdridge, Michele Lee, Susan Watson, Marlo Thomas, Sally Kellerman, Ellen Burstyn (then billed as Ellen McRae), Barbara Babcock, Sherry Jackson, and Danielle De Metz. Yvonne Craig appeared in the opening credits and the closing sequence of the pilot film used to sell the series to CBS, but did not appear in the actual episode, "Caper at The Bijou", when it was broadcast. She eventually played five different girlfriends on the show, more than any other actress.
Actress Sherry Alberoni, an original Mickey Mouse Club "Mouseketeer", played one of Zelda Gilroy's sisters in the 1960 episode "Dobie Spreads a Rumor".
