Gwyneth Paltrow

Rosemary

Jack Black

Hal

Jason Alexander

Mauricio

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

Kyle Gass

Artie

Joshua 'Li'iBoy' Shintani

Li'iboy

Laura Kightlinger

Jen

Sasha Joseph Neulinger

Young Hal

Nan Martin

Tanya Peeler

Erinn Bartlett

Bella

Fawn Irish

Spastic Bella

John-Eliot Jordan

Fuel Pizza Waiter

Jill Christine Fitzgerald

Mrs. Shanahan

Daniel Greene

Doctor

Danny Murphy

Cabbie

Steve Tyler

McIntosh Waiter

Darius Rucker

Capital Grille Maitre D'

Bonnie Aarons

Spastic Friend #1

Brian Mone

Board Member #1

Sayed Badreya

Doctor Sayed

Bob Mone

Board Member #2

Molly Shannon

Mrs. Mary Larson (uncredited)

Don Gavin

David Bouley

Sascha Knopf

Gorgeous Tanya

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

Mary Wigmore

Cute Tiffany

Steve Tyler

McIntosh Waiter

John Dennis

Capital Grille Host

Manon von Gerkan

Lindy

Will Coogan

Punk #1

Lyndon Byers

Punk #2

Sara Stout

Babe on Dance Floor

Lisa Brounstein

Spastic Friend #2

Herbie Flynn

Homeless Man #1

Michael Corrente

Homeless Man #2

Ron Darling

Other Li'iboy

Anne E. Hodgson

Pretty Nurse

Kelly McRorie

Bar Girl

Dean R. Palozej

Bartender

Dede Kinerk

Party Friend

David A. Kipper

Department Store Clerk

David Getz

Dr. James Uler

Jesse Peter

Sick Kid #1

A.B. Cassidy

Sick Kid #2

Sean Gildea

Pool Dad

Robby Johns

Kid in Tree

Tiffany Burke

Soda Shop Waitress

Hillary Matthews

Pretty Girl with Puppy

Nicholas Theodore Nemeth

Night Club Goer

Anthony Robbins

Self

Stacy Marie Fuson

Night Club Goer #2 (as Stacey Fuson)

Ashley B. Howard

Night Club Goer #2

Evgeniy Ivanov

(dooble voice)