Kastner also starred in the 1968–1969 ABC sitcom The Ugliest Girl in Town, where he played Timothy Blair, a man who dressed in drag as a favour to his photographer brother.
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His breakthrough role was in the title role of the 1967 Francis Ford Coppola comedy You're a Big Boy Now, also starring Rip Torn, Geraldine Page and Elizabeth Hartman.
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You're a Big Boy Now is a 1966 film with Peter Kastner, Elizabeth Hartman, Geraldine Page, Julie Harris and Karen Black, written and directed by Francis Ford Coppola based on a 1963 novel, also titled You're a Big Boy Now, by David Benedictus.