Jon Favreau as Mike Peters

Vince Vaughn as Trent Walker

Ron Livingston as Rob

Patrick Van Horn as Sue

Alex Désert as Charles

Heather Graham as Lorraine

Deena Martin as Christy

Katherine Kendall as Lisa

Brooke Langton as Nikki

Blake Lindsley as Girl with Cigar

Kevin James Kelly as Vegas Dealer

Stephanie Ittleson as Vegas Waitress

Vernon Vaughn as $100 Gambler

Joan Favreau as $5 Winner

Rio Hackford as Skully

Jan Dykstra as Girl at Party

Maddie Corman as Peek-a-boo Girl

Marty & Elayne as Dresden Lounge Act

Sheri Rosenblum as $100 Gambler

Stasea Rosenblum as $100 Gambler

Pamela Shaw as $5 Gambler

Tom Alley as Pit Boss

Reverend Phil Dixon as Lounge Lizard

Ashley M. Rogers as Bartender

Jay Diola as Skully's Crew / Derby Dancer

Nicholas Gagliarducci as Skully's Crew

David Gould as Skully's Crew

Bill Phillips as Skully's Crew

Mansur Hamud as Pink Dot Guy

Ahmed Ahmed as Party Mystery Guy

Eufemia Plimpton as Derby Lady

Melinda Starr as Derby Lady

Samantha Lemole as Dresden Lady

Jessica Buchman as Dresden Lady

Caroline O'Meara as Diner Waitress

Gary Auerbach as Derby Doorman

Brad Halvorson as Derby Doorman

Christopher R. Joyce as Diner Patron

Edward Rissien as Diner Patron

Jenna Rissien as Diner Patron

Mark Smith as Diner Patron

John Abrham as Derby Dancer

Rachel Gallaghan as Derby Dancer

Lisa Guerriero as Derby Dancer

Thomas Hall as Derby Dancer

Damiana Kamishin as Derby Dancer

Curtis Lindersmith as Derby Dancer

Jennifer Lucero as Derby Dancer

Pinki Marsolek as Derby Dancer

Rhonda Martin as Derby Dancer

Martina Migenes as Derby Dancer

Paul Mojica as Derby Dancer

Sam Mollo as Derby Dancer

Jacob Morris as Derby Dancer

Michael Scott as Derby Dancer

Bernard Serrano as Derby Dancer

Rosalind Smith as Derby Dancer

Molly Stern as Derby Dancer

Johnny Walker as Derby Dancer

Lisa Wolstein as Derby Dancer

Stephen Gaghan as Onlooker at Model Party Entrance (uncredited)