Stay Cool

Stay Cool

Shoulda. Coulda. Woulda.

2009 en 94 minutes

Rating: 4.9

Plot

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.

Trailer

Cast

Mark Polish

Mark Polish

Henry McCarthy

Winona Ryder

Winona Ryder

Scarlet Smith

Sean Astin

Sean Astin

Big Girl

Hilary Duff

Hilary Duff

Shasta O'Neil

Josh Holloway

Josh Holloway

Wino

Jessica St. Clair

Jessica St. Clair

Darcy Portola

Frances Conroy

Frances Conroy

Mrs. Leuchtenberger

Marc Blucas

Marc Blucas

Brad Nelson

Joanna Cassidy

Joanna Cassidy

Mrs. Smith

Dee Wallace

Dee Wallace

Mrs. McCarthy

Michael Gross

Michael Gross

Mr. McCarthy

Jon Cryer

Jon Cryer

Javier

Chevy Chase

Chevy Chase

Principal Marshall

Ken Johnson

Ken Johnson

Mr. O'Neil

Jessica Schatz

Jessica Schatz

Mrs. O'Neil

Scott Michael Campbell

Scott Michael Campbell

Officer Bird

Blake Adams

Blake Adams

Cop

Catherine Black

Catherine Black

Goth Girl

Jenn Shagrin

Jenn Shagrin

Jungle Journalist #1

Josh Sussman

Josh Sussman

Jungle Journalist #2

Jane Sheldon

Jane Sheldon

Goth Girl Singer

Clark Hunter

Clark Hunter

River Village Guard #1

John A. Keim

John A. Keim

River Village Guard #2

Jack Salvatore, Jr.

Jack Salvatore, Jr.

Student in Hallway

Nick Thurston

Nick Thurston

Party Kid

Kelly Wagner

Kelly Wagner

Nurse

Ashley Bell

Ashley Bell

Valedictorian

David Shackelford

David Shackelford

John John

Ryan Best

Ryan Best

Disc Jockey

Bon Ogle

Bon Ogle

Bookstore Employee

Emily Happe

Emily Happe

WRHS TV Host

Victoria Johnson

Victoria Johnson

Student Hollywood Reporter

Max Thieriot

Max Thieriot

Shasta's Boyfriend

Brian Austin Green

Brian Austin Green

Narrator

Similar Movies

She's Out of His Mind

She's Out of His Mind

en

March 27, 2022

Hot for Teacher

Hot for Teacher

ko

November 16, 2006

Sex, Shame & Tears

Sex, Shame & Tears

es

June 18, 1999

Up on the Roof

Up on the Roof

en

March 24, 2023

Cutting Class

Cutting Class

en

April 24, 1989

LOL (Laughing Out Loud)

LOL (Laughing Out Loud)

fr

February 4, 2009

My Bodyguard

My Bodyguard

en

July 11, 1980

Booty Call

Booty Call

en

February 26, 1997

The Pom Pom Girls

The Pom Pom Girls

en

May 1, 1976

Topless

Topless

en

February 13, 2023

NORMAN

NORMAN

en

March 23, 2023

Life Partner

Life Partner

hi

August 14, 2009

High Spirits

High Spirits

en

November 18, 1988

Watch Your Step

Watch Your Step

sh

January 10, 1984

All's Well, Ends Well 2009

All's Well, Ends Well 2009

cn

January 22, 2009

Society

Society

en

May 13, 1989