Stay Cool
"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.
Cast (47)
Winona Ryder
Scarlet Smith
Mark Polish
Henry McCarthy
Sean Astin
Big Girl
Hilary Duff
Shasta O'Neil
Josh Holloway
Wino
Jon Cryer
Javier
Chevy Chase
Principal Marshall
Jessica St. Clair
Darcy Portola
Frances Conroy
Mrs. Leuchtenberger
Marc Blucas
Brad Nelson
Joanna Cassidy
Mrs. Smith
Dee Wallace
Mrs. McCarthy
Michael Gross
Mr. McCarthy
Ken Johnson
Mr. O'Neil
Jessica Schatz
Mrs. O'Neil
Scott Michael Campbell
Officer Bird
Blake Adams
Cop
Catherine Black
Goth Girl
Jenn Shagrin
Jungle Journalist #1
Josh Sussman
Jungle Journalist #2
Jane Sheldon
Goth Girl Singer
Clark Hunter
River Village Guard #1
John A. Keim
River Village Guard #2
Jack Salvatore, Jr.
Student in Hallway
Nick Thurston
Party Kid
Kelly Wagner
Nurse
Ashley Bell
Valedictorian
David Shackelford
John John
Ryan Best
Disc Jockey
Emily Happe
WRHS TV Host
Bon Ogle
Bookstore Employee
Victoria Johnson
Student Hollywood Reporter
Max Thieriot
Shasta's Boyfriend
Brian Austin Green
Narrator
Matthew Berke
Tree Dwelling High School Student
Amanda Elliott
Prom Date Girl
Irvin Scott Guillermo
Senior
Shawn McDonald
Franky (as Shawn Ronell McDonald)
Brent Rode
Cannonball Guy
Nicole Smolen
Student
Max Tsarev
Wild Prom Boy / Basketball Player
Brad Benedict
Senior Stud (uncredited)
Ashleigh Nicole Johnson
Party Girl (uncredited)
Michael Justice
Senior (uncredited)
Silver Tree
Angie (uncredited)
Karmyn Tyler
Beauty Shop Receptionist (uncredited)
Matthew Woodward
Skater Kid (uncredited)
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