Matt Damon as Bob

Greg Kinnear as Walt

Eva Mendes as April

Wen Yann Shih as May

Pat Crawford Brown as Mimmy

Ray 'Rocket' Valliere as Rocket

Tommy Songin as Tommy

Terence Bernie Hines as Moe

Cher as Cher

Jackie Flynn as Howard

Seymour Cassel as Morty O'Reilly

Griffin Dunne as Griffin Dunne

Bridget Tobin as Vineyard Cutie

Danny Murphy as Dicky

Malcolm G. Chase Jr. as Vineyard Buddy

Steve Cerrone as Dart in Head Guy

Docky as Short-Fused Geezer

Will Coogan as Eddie

Skyler Stone as George

Leslie Monroe as Vineyard Patron

Mike Cerrone as Hockey Stud

Michael Lee Merrins as Umpire #1

Jonathan Cauff as Umpire #2

Sean Gildea as Baseball Coach

Michael Callan as Fox Prexy

Dane Cook as Officer Fraioli

Steve Tyler as Officer Reney

Peter Dante as Officer Hill

Benjamin Koldyke as Officer Johnson

Jessica Cauffiel as Bar Hottie

Roger Fan as Executive #1

Jennifer Burnham as Executive #2

Elaine Curtis as Cher's Assistant

Gary Valentine as Wes

Mariann Neary as Purse Babe #1

Terez Kocsis as Purse Babe #2

Ben Carson as Head Surgeon

Sayed Badreya as Assisting Surgeon

Hillary Matthews as Nurse's Aide

Dan Geraci as Handsome Hospital Orderly

Bob Mone as Hospital Heartthrob

Brian Mone as Tall Man

Catherine McCord as Jogger Babe #1

Kelly Albanese as Jogger Babe #2

Paulina Neely as Jogger Babe #3

Daniel Greene as Mr. Tourist

Brian Hayes Currie as Laughing Director

Tracy Ashton as Casting Agent #2

Ellen Jacoby as Casting Agent #7

Doug Jones as Space Alien #2

Lin Shaye as Makeup Babe

Johnny Cicco as Porno Director

Juliet Cariaga as Marianna Trench

Jeff Ross as Beaze Security Guard

Googy Gress as Pete Peterson

Jay Leno as Jay Leno

Gene Feldman as Beaze Assistant Director

Kiele Sanchez as Pepper Spray Cutie

Luke Wilson as Luke Wilson

Nikki Tyler-Flynn as Double Bubble Casting Agent

Tom Brady as Computer Geek #1

Lawyer Milloy as Computer Geek #2

George Christy as Beaze Stagehand

Stephen Saux as Drive-by Heckler

Tracey Ruggiero as Barney's Waitress

Rhona Mitra as Bus Stop Bombshell

Ashley B. Howard as Blonde Double Bubble Babe

Monika Kramlik as Brunette Double Bubble Babe

Adam Shankman as Choreographer / Waiter

Cam Neely as MV Hockey Player

Lisa Ratzin as Dancer #3

Apple Farrelly as LA Restaurant Patron

Remy Thorne as MV Sideline Fan

Troy Brown as Pro Golf Tour Caddy

Ryan Biegel as Bonnie & Clyde Musical Audience

Frankie Muniz as Frankie Muniz (uncredited)

Deborah Smith Ford as Theatre Patron (uncredited)

Mary Hart as Mary Hart (uncredited)

Meryl Streep as Meryl Streep (uncredited)

Bella Thorne as MV Sideline Fan (uncredited)

Jesse Ventura as Jesse Ventura (uncredited)

Fernanda Lima as Fernanda Lima (uncredited)