Shoulda. Coulda. Woulda.
4.9
94 min
A successful author is forced to confront an unrequited high school crush when he returns home to deliver a commencement address to graduating seniors. Shasta O'Neil, a sexy high school senior flirts with the visiting author and invites him to the prom.
Name | Character | Team | |
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Mark Polish | Henry McCarthy | Unowned |
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Winona Ryder | Scarlet Smith | The Free Refills |
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Sean Astin | Big Girl | Unowned |
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Hilary Duff | Shasta O'Neil | Unowned |
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Josh Holloway | Wino | Unowned |
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Jessica St. Clair | Darcy Portola | Unowned |
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Frances Conroy | Mrs. Leuchtenberger | Unowned |
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Marc Blucas | Brad Nelson | Unowned |
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Joanna Cassidy | Mrs. Smith | Unowned |
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Dee Wallace | Mrs. McCarthy | Unowned |
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Michael Gross | Mr. McCarthy | Unowned |
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Jon Cryer | Javier | Unowned |
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Chevy Chase | Principal Marshall | Unowned |
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Ken Johnson | Mr. O'Neil | Unowned |
Jessica Schatz | Mrs. O'Neil | Unowned | |
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Scott Michael Campbell | Officer Bird | Unowned |
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Blake Adams | Cop | Unowned |
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Catherine Black | Goth Girl | Unowned |
Jenn Shagrin | Jungle Journalist #1 | Unowned | |
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Josh Sussman | Jungle Journalist #2 | Unowned |
Jane Sheldon | Goth Girl Singer | Unowned | |
Clark Hunter | River Village Guard #1 | Unowned | |
John A. Keim | River Village Guard #2 | Unowned | |
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Jack Salvatore, Jr. | Student in Hallway | Unowned |
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Nick Thurston | Party Kid | Unowned |
Kelly Wagner | Nurse | Unowned | |
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Ashley Bell | Valedictorian | Unowned |
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David Shackelford | John John | Unowned |
Ryan Best | Disc Jockey | Unowned | |
Bon Ogle | Bookstore Employee | Unowned | |
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Emily Happe | WRHS TV Host | Unowned |
Victoria Johnson | Student Hollywood Reporter | Unowned | |
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Max Thieriot | Shasta's Boyfriend | Unowned |
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Brian Austin Green | Narrator | Unowned |