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Stay Cool (2011)

Genres: Comedy, Romance

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.

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