Willy/Milly

Milly Niceman is a fourteen-year-old girl who has grown frustrated with her mother's attempts to curtail her tomboyish nature. Her mother, Doris, believes that Milly's actions are inappropriate for a girl, and that she'd be better off showing more interest in dances and dresses. When her best friend's younger brother, Malcolm, sells her a spell that will grant her deepest wish, that will only work during the upcoming eclipse, Milly jumps at the chance. She performs the spell, and believes that it has failed. The next morning, Milly discovers that not only was the spell successful, but it turned her into a boy. She tells her family about what happened, and to her surprise, her father encourages her to explore her new masculinity.

As a result, Milly changes her name to "Willy", and begins attending a new school as a transfer student. Milly initially takes well to her new persona and gender, but eventually becomes conflicted when she begins to realize that life isn't necessarily easier as a boy and that she has feelings for her friend Alfie, who is equally confused about his feelings for "Willy". By the film's end, Milly decides to become female once more. Malcolm sells Milly a wishing stone that she is to throw at her favorite star at 12:03 during a star shower. She turns back into a girl again.

• Pamela Adlon as Milly / Willy Niceman (as Pamela Segall)
• Eric Gurry as Alfie
• Mary Tanner Bailey as Stephanie (as Mary Tanner)
• John Glover as Fred Niceman
• Patty Duke as Doris Niceman
• Seth Green as Malcolm
• JD Cullum as Tom
• Corey Parker as Lopez
• Jeb Ellis-Brown as Harry
• Taryn Grimes as Cynthia
• Diane Bogino as Doctor #1
• Milton Chaikin as Doctor #2
• Bobby Emmrich as Luke
• Mike McGehee as Smiley
• Robin Jackson as Witch

Providence Journal commented that the film could have worked it if had been "played for hilarious farce a la Tootsie, or as an examination of the psychological traumas that [Milly]/Willy undergoes".[5] The Sun-Sentinel panned the film as "so shallow, boring and half-baked that one wonders if anyone looked at the finished product before distribution".[6] The Daily News of Los Angeles and Los Angeles Times both gave mixed reviews for the Willy/Milly, with the Los Angeles Times remarking that while the film "doesn't really function well as a comedy" it did have some appeal.[3][7]

Jack Halberstam, in the book Female Masculinity, objected to the movie's presentation of "family pressures to be one of two available genders" and reinforcement of "binary gender laws", further opining it was "troubling in the way that it resolves the problem of intersexuality or transsexuality by abjecting gender ambiguity."[8]

• Willy/Milly at IMDb
• Willy/Milly at the American Film Institute Catalog
• Willy/Milly at Box Office Mojo