Jack Black

Character: Hal Larson

Gwyneth Paltrow

Character: Rosemary Shanahan

Jason Alexander

Character: Mauricio Wilson

Joe Viterelli

Character: Steve Shanahan

Rene Kirby

Character: Walt

Bruce McGill

Character: Reverend Larson

Tony Robbins

Character: Tony Robbins

Susan Ward

Character: Jill

Zen Gesner

Character: Ralph

Brooke Burns

Character: Katrina

Rob Moran

Character: Second Tiffany

Joshua 'Li'iBoy' Shintani

Character: Li'iboy

Kyle Gass

Character: Artie

Laura Kightlinger

Character: Jen

Nan Martin

Character: Tanya Peeler

Sasha Joseph Neulinger

Character: Young Hal

John-Eliot Jordan

Character: Fuel Pizza Waiter

Jill Christine Fitzgerald

Character: Mrs. Shanahan

Erinn Bartlett

Character: Bella

Fawn Irish

Character: Spastic Bella

Daniel Greene

Character: Doctor

Danny Murphy

Character: Cabbie

Brian Mone

Character: Board Member #1

Bob Mone

Character: Board Member #2

Don Gavin

Character: David Bouley

Leslie DeAntonio

Character: Helga

Libby Langdon

Character: Waitress

Gigi Moran

Character: Nurse #1

Caryl Lippman West

Character: Nurse #2

Brianna Gardner

Character: Cadence

Mariann Neary

Character: Information Attendant #1

Christal Handy

Character: Information Attendant #2

Jackie Flynn

Character: Fuel Pizza Manager

Sascha Knopf

Character: Gorgeous Tanya

Mary Wigmore

Character: Cute Tiffany

Steve Tyler

Character: McIntosh Waiter

Darius Rucker

Character: Capital Grille Maitre D'

John Dennis

Character: Capital Grille Host

Manon von Gerkan

Character: Lindy

Will Coogan

Character: Punk #1

Lyndon Byers

Character: Punk #2

Sara Stout

Character: Babe on Dance Floor

Bonnie Aarons

Character: Spastic Friend #1

Lisa Brounstein

Character: Spastic Friend #2

Herbie Flynn

Character: Homeless Man #1

Michael Corrente

Character: Homeless Man #2

Ron Darling

Character: Other Li'iboy

Anne E. Hodgson

Character: Pretty Nurse

Kelly McRorie

Character: Bar Girl

Dean R. Palozej

Character: Bartender

Dede Kinerk

Character: Party Friend

Dr. David A. Kipper

Character: Department Store Clerk

Sayed Badreya

Character: Doctor Sayed

David Getz

Character: Dr. James Uler

Jesse Peter

Character: Sick Kid #1

Abe Farrelly

Character: Sick Kid #2

Sean Gildea

Character: Pool Dad

Robby Johns

Character: Kid in Tree

Tiffany Burke

Character: Soda Shop Waitress

Hillary Matthews

Character: Pretty Girl with Puppy

Nick Nemeth

Character: Night Club Goer

Molly Shannon

Character: Mrs. Mary Larson (uncredited)

Stacy Fuson

Character: Night Club Goer #2 (as Stacey Fuson)

Ashley B. Howard

Character: Night Club Goer #2

Apple Farrelly

Character: Hospital Intensive Care Unit Staff & Patient (as Apple Kocsis)

Kevin Biegel

Character: Night Club Goer

Ryan Biegel

Character: Night Club Goer

Warren Tashjian

Character: Freedom Park Goer

Thomas Jordan

Character: Wachusett Mtn. Skier