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

Manhattan

Manhattan

en

April 25, 1979

Annie Hall

Annie Hall

en

April 19, 1977

Hurricane Bianca

Hurricane Bianca

en

June 3, 2016

The Great Dictator

The Great Dictator

en

October 15, 1940

School of Rock

School of Rock

en

October 3, 2003

Bring It On

Bring It On

en

August 25, 2000

The Front

The Front

en

September 17, 1976

Trick

Trick

en

July 23, 1999

50 First Dates

50 First Dates

en

February 13, 2004

The Master and The Loser

The Master and The Loser

fr

April 5, 2023

My First Love

My First Love

en

December 4, 1988

Take Down

Take Down

en

January 13, 1979

Breakfast at Tiffany's

Breakfast at Tiffany's

en

October 6, 1961

Amélie

Amélie

fr

April 25, 2001

Arsenic and Old Lace

Arsenic and Old Lace

en

September 1, 1944

The Apartment

The Apartment

en

June 21, 1960

Chocolat

Chocolat

en

December 22, 2000

Notting Hill

Notting Hill

en

May 21, 1999

Thumbsucker

Thumbsucker

en

September 16, 2005

Gym Classes

Gym Classes

it

May 20, 2024