Stay Cool poster

Shoulda. Coulda. Woulda.

Stay Cool

4.820111h 34mPG-13

ComedyRomance

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.

Directed by Michael Polish

Behind the scenes

Movie screenshots & stills

Stay Cool still 1

Stay Cool still 2

Stay Cool still 3

Stay Cool still 4

Stay Cool still 5

CAST

The people behind the story

Winona Ryder

Winona RyderScarlet Smith

Mark Polish

Mark PolishHenry McCarthy

Sean Astin

Sean AstinBig Girl

Hilary Duff

Hilary DuffShasta O'Neil

Josh Holloway

Josh HollowayWino

Jon Cryer

Jon CryerJavier

Chevy Chase

Chevy ChasePrincipal Marshall

Jessica St. Clair

Jessica St. ClairDarcy Portola