Shoulda. Coulda. Woulda.
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.
Made in US
4.8/10
2011
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Cast
Winona Ryder
As Scarlet Smith
Mark Polish
As Henry McCarthy
Sean Astin
As Big Girl
Hilary Duff
As Shasta O'Neil
Josh Holloway
As Wino
Jon Cryer
As Javier
Chevy Chase
As Principal Marshall
Jessica St. Clair
As Darcy Portola
Frances Conroy
As Mrs. Leuchtenberger
Marc Blucas
As Brad Nelson
Joanna Cassidy
As Mrs. Smith
Dee Wallace
As Mrs. McCarthy
Michael Gross
As Mr. McCarthy
Ken Johnson
As Mr. O'Neil
Jessica Schatz
As Mrs. O'Neil
Scott Michael Campbell
As Officer Bird
Blake Adams
As Cop
Catherine Black
As Goth Girl
Jenn Shagrin
As Jungle Journalist #1
Josh Sussman
As Jungle Journalist #2
Jane Sheldon
As Goth Girl Singer
Clark Hunter
As River Village Guard #1
John A. Keim
As River Village Guard #2
Jack Salvatore, Jr.
As Student in Hallway
Nick Thurston
As Party Kid
Kelly Wagner
As Nurse
Ashley Bell
As Valedictorian
David Shackelford
As John John
Ryan Best
As Disc Jockey
Emily Happe
As WRHS TV Host
Bon Ogle
As Bookstore Employee
Victoria Johnson
As Student Hollywood Reporter
Max Thieriot
As Shasta's Boyfriend
Brian Austin Green
As Narrator
Matthew Berke
As Tree Dwelling High School Student
Amanda Elliott
As Prom Date Girl
Irvin Scott Guillermo
As Senior
Shawn McDonald
As Franky (as Shawn Ronell McDonald)
Brent Rode
As Cannonball Guy
Nicole Smolen
As Student
Max Tsarev
As Wild Prom Boy / Basketball Player
Brad Benedict
As Senior Stud (uncredited)
Ashleigh Nicole Johnson
As Party Girl (uncredited)
Michael Justice
As Senior (uncredited)
Silver Tree
As Angie (uncredited)
Karmyn Tyler
As Beauty Shop Receptionist (uncredited)
Matthew Woodward
As Skater Kid (uncredited)
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