Stay Cool 10 years old

Shoulda. Coulda. Woulda.

The film centers on a successful author who 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.


Winona Ryder
Winona Ryder

Scarlet Smith

Sean Astin
Sean Astin

Big Girl

Max Thieriot
Max Thieriot

Shasta's Boyfriend

Chevy Chase
Chevy Chase

Principal Marshall

Hilary Duff
Hilary Duff

Shasta O'Neil

Stay Cool Cast

Name Character
Joanna Cassidy She was 66, now 76 years old as Mrs. Smith
Sean Astin He was 40, now 50 years old as Big Girl
Winona Ryder She was 39, now 49 years old as Scarlet Smith
Hilary Duff She was 23, now 34 years old as Shasta O'Neil
Max Thieriot He was 22, now 33 years old as Shasta's Boyfriend
Mark Polish He was 40, now 50 years old as Henry McCarthy
Marc Blucas He was 39, now 49 years old as Brad Nelson
Chevy Chase He was 67, now 78 years old as Principal Marshall
Dee Wallace She was 62, now 72 years old as Mrs. McCarthy
Michael Gross He was 64, now 74 years old as Mr. McCarthy
Jon Cryer He was 46, now 56 years old as Javier
Josh Holloway He was 42, now 52 years old as Wino

Stay Cool Crew

Name Department
M. David Mullen as Director of Photography. He was 49 (now 59) years old Camera
Stay Cool poster
Stay Cool (10 years)

Shoulda. Coulda. Woulda.

  • Release day: Friday, September 16, 2011
  • Runtime: 94 minutes
  • Budget: 4500000.00