Jack Black

Hal Larson

Gwyneth Paltrow

Rosemary Shanahan

Jason Alexander

Mauricio Wilson

Joe Viterelli

Steve Shanahan

Rene Kirby

Walt

Bruce McGill

Reverend Larson

Tony Robbins

Tony Robbins

Susan Ward

Jill

Zen Gesner

Ralph

Brooke Burns

Katrina

Rob Moran

Second Tiffany

Joshua 'Li'iBoy' Shintani

Li'iboy

Kyle Gass

Artie

Laura Kightlinger

Jen

Nan Martin

Tanya Peeler

Sasha Joseph Neulinger

Young Hal

John-Eliot Jordan

Fuel Pizza Waiter

Jill Christine Fitzgerald

Mrs. Shanahan

Erinn Bartlett

Bella

Fawn Irish

Spastic Bella

Daniel Greene

Doctor

Danny Murphy

Cabbie

Brian Mone

Board Member #1

Bob Mone

Board Member #2

Don Gavin

David Bouley

Leslie DeAntonio

Helga

Libby Langdon

Waitress

Gigi Moran

Nurse #1

Caryl Lippman West

Nurse #2

Brianna Gardner

Cadence

Mariann Neary

Information Attendant #1

Christal Handy

Information Attendant #2

Jackie Flynn

Fuel Pizza Manager

Sascha Knopf

Gorgeous Tanya

Mary Wigmore

Cute Tiffany

Steve Tyler

McIntosh Waiter

Darius Rucker

Capital Grille Maitre D'

John Dennis

Capital Grille Host

Manon von Gerkan

Lindy

Will Coogan

Punk #1

Bonnie Aarons

Spastic Friend #1

Michael Corrente

Homeless Man #2

Dr. David A. Kipper

Department Store Clerk

Sayed Badreya

Doctor Sayed

Nick Nemeth

Night Club Goer

Molly Shannon

Mrs. Mary Larson (uncredited)

Kevin Biegel

Night Club Goer

Thomas Jordan

Wachusett Mtn. Skier