Skippy (1997)
Directed by Denis Adam Zervos
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Synopsis by Mark Deming
Can a beautiful starlet find happiness with a overly confident fool? Well, the fool certainly hopes so in this offbeat comedy. Skippy (Joe Convery) is a twentysomething guy who is cheerful and well-meaning; however, he's not terribly bright, socially inept, and the unfortunate possessor of one of the worst fashion senses in the history of Western civilization. Skippy hears an interview with lovely movie star Julie Fontaine (Paget Brewster), in which she says she's tired of dating actors and wants to settle down with an ordinary guy. Mistakenly assuming he'd fit the bill, Skippy heads for Hollywood, where with the dubious assistance of his friend, Larry (Timothy Patrick O'Brien), he sets out to meet and win the heart of Ms. Fontaine.