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"Shoulda. Coulda. Woulda."

2009-04-23 Comedy 1hr 34m

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.

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Storyline

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.

  • Released
    2009-04-23
  • Revenue
    n/a
  • Budget
    $4,500,000
  • Runtime
    1hr 34m
  • Genre
    Comedy, Romance
  • Status
    Released
  • Language
    English
  • imdb-logo
    4.9
  • Production
    Initiate Productions

Crew

Michael Polish
Director
Mark Polish
Writer
Keywords:
high school narration romcom speech prom writer hometown high school sweetheart school commencement return to hometown second chance romance

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Cast

Mark Polish

Mark Polish
Henry McCarthy
Winona Ryder

Winona Ryder
Scarlet Smith
Sean Astin

Sean Astin
Big Girl
Hilary Duff

Hilary Duff
Shasta O'Neil
Josh Holloway

Josh Holloway
Wino
Jessica St. Clair

Jessica St. Clair
Darcy Portola
Frances Conroy

Frances Conroy
Mrs. Leuchtenberger
Marc Blucas

Marc Blucas
Brad Nelson
Joanna Cassidy

Joanna Cassidy
Mrs. Smith
Dee Wallace

Dee Wallace
Mrs. McCarthy
Michael Gross

Michael Gross
Mr. McCarthy
Jon Cryer

Jon Cryer
Javier
Chevy Chase

Chevy Chase
Principal Marshall
Ken Johnson

Ken Johnson
Mr. O'Neil
Jessica Schatz

Jessica Schatz
Mrs. O'Neil
Scott Michael Campbell

Scott Michael Campbell
Officer Bird
Blake Adams

Blake Adams
Cop
Catherine Black

Catherine Black
Goth Girl
Jenn Shagrin

Jenn Shagrin
Jungle Journalist #1
Josh Sussman

Josh Sussman
Jungle Journalist #2
Jane Sheldon

Jane Sheldon
Goth Girl Singer
Clark Hunter

Clark Hunter
River Village Guard #1
John A. Keim

John A. Keim
River Village Guard #2
Jack Salvatore, Jr.

Jack Salvatore, Jr.
Student in Hallway
Nick Thurston

Nick Thurston
Party Kid
Kelly Wagner

Kelly Wagner
Nurse
Ashley Bell

Ashley Bell
Valedictorian
David Shackelford

David Shackelford
John John
Ryan Best

Ryan Best
Disc Jockey
Bon Ogle

Bon Ogle
Bookstore Employee
Emily Happe

Emily Happe
WRHS TV Host
Victoria Johnson

Victoria Johnson
Student Hollywood Reporter
Max Thieriot

Max Thieriot
Shasta's Boyfriend
Brian Austin Green

Brian Austin Green
Narrator

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