Stay Cool

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.

Full Cast of Stay Cool

Chevy Chase as Principal Marshall

Chevy Chase

as Principal Marshall

Cornelius Crane "Chevy" Chase (born October 8, 1943) is an American comedian, writer, and television and film actor, ...

Michael Gross as Mr. McCarthy

Michael Gross

as Mr. McCarthy

From Wikipedia, the free encyclopedia. Michael Gross (born June 21, 1947) is an American television, movie, and stag...

Dee Wallace as Mrs. McCarthy

Dee Wallace

as Mrs. McCarthy

Dee Wallace (born 14 December 1948) is an American actress and comedienne. She is perhaps best known for her roles in...

Josh Holloway as Wino

Josh Holloway

as Wino

Josh Lee Holloway (born July 20, 1969) is an American actor best known for his roles as James "Sawyer" Ford on the te...

Hilary Duff as Shasta O'Neil

Hilary Duff

as Shasta O'Neil

Hilary Erhard Duff (born September 28, 1987) is an American actress, singer, and songwriter. She is the recipient of ...

Jon Cryer as Javier

Jon Cryer

as Javier

​Jonathan Niven Cryer (born April 16, 1965) is an American actor, screenwriter, director, and film producer. He is th...

Winona Ryder as Scarlet Smith

Winona Ryder

as Scarlet Smith

Winona Laura Horowitz (born October 29, 1971), known professionally as Winona Ryder, is an American actress. She is t...

Sean Astin as Big Girl

Sean Astin

as Big Girl

Sean Astin (born February 25, 1971) is an American film actor, director, and producer better known for his film roles...