Jack Black as Hal

Gwyneth Paltrow as Rosemary

Jason Alexander as Mauricio

Joe Viterelli as Steve Shanahan

Rene Kirby as Walt

Bruce McGill as Reverend Larson

Tony Robbins as Tony Robbins

Susan Ward as Jill

Zen Gesner as Ralph

Brooke Burns as Katrina

Rob Moran as Second Tiffany

Joshua 'Li'iBoy' Shintani as Li'iboy

Kyle Gass as Artie

Laura Kightlinger as Jen

Nan Martin as Tanya Peeler

Sasha Joseph Neulinger as Young Hal

John-Eliot Jordan as Fuel Pizza Waiter

Jill Christine Fitzgerald as Mrs. Shanahan

Erinn Bartlett as Bella

Fawn Irish as Spastic Bella

Daniel Greene as Doctor

Danny Murphy as Cabbie

Brian Mone as Board Member #1

Bob Mone as Board Member #2

Don Gavin as David Bouley

Leslie DeAntonio as Helga

Libby Langdon as Waitress

Gigi Moran as Nurse #1

Caryl Lippman West as Nurse #2

Brianna Gardner as Cadence

Mariann Neary as Information Attendant #1

Christal Handy as Information Attendant #2

Jackie Flynn as Fuel Pizza Manager

Sascha Knopf as Gorgeous Tanya

Mary Wigmore as Cute Tiffany

Steve Tyler as McIntosh Waiter

Darius Rucker as Capital Grille Maitre D'

John Dennis as Capital Grille Host

Manon von Gerkan as Lindy

Will Coogan as Punk #1

Lyndon Byers as Punk #2

Sara Stout as Babe on Dance Floor

Bonnie Aarons as Spastic Friend #1

Lisa Brounstein as Spastic Friend #2

Herbie Flynn as Homeless Man #1

Michael Corrente as Homeless Man #2

Ron Darling as Other Li'iboy

Anne E. Hodgson as Pretty Nurse

Kelly McRorie as Bar Girl

Dean R. Palozej as Bartender

Dede Kinerk as Party Friend

Dr. David A. Kipper as Department Store Clerk

Sayed Badreya as Doctor Sayed

David Getz as Dr. James Uler

Jesse Peter as Sick Kid #1

Abe Farrelly as Sick Kid #2

Sean Gildea as Pool Dad

Robby Johns as Kid in Tree

Tiffany Burke as Soda Shop Waitress

Hillary Matthews as Pretty Girl with Puppy

Nick Nemeth as Night Club Goer

Molly Shannon as Mrs. Mary Larson (uncredited)

Stacy Fuson as Night Club Goer #2 (as Stacey Fuson)

Ashley B. Howard as Night Club Goer #2

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

Kevin Biegel as Night Club Goer

Ryan Biegel as Night Club Goer