

30/03/2001
College buddies chip in and promise that the group's last unmarried man will collect a cash pot. Seven years later, the kitty is worth $500,000 -- money Michael needs to pay a gambling debt. Problem is, the only other single guy is a hopeless womanizer!

Jerry O'Connell
as Michael Delaney

Shannon Elizabeth
as Officer Natalie Parker

Jake Busey
as Kyle Brenner

Horatio Sanz
as Steve

Bernie Casey
as Officer Hurley

Jaime Pressly
as Tricia

David Ogden Stiers
as Dr. Crawford

Travis Fine
as Jan

Heather Stephens
as Jill

Julia Schultz
as Shelby

Scott Beehner
as Max

Kam Heskin
as Kimberly

J. Kenneth Campbell
as Mr. MacDonald

Brandi Andres
as Kelly

John Patrick White
as Garry

David St. James
as Priest

Buck Kartalian
as Grandfather MacDonald

Alexa Power
as Grandmother MacDonald

Amber Smith
as Gorgeous Redhead

Dakota Fanning
as Little Girl in Park

Anthony Azizi
as Sikh Elvis Chaplain

Billy Hufsey
as Pit Boss

Damon Williams
as Tony

Lauren Moore
as Janet

Monica Serene Garnich
as Barfing Girl

Tracy Kay
as Golfing Girl

Nina Kaczorowski
as Cheating Wife

Sandra Taylor
as Nurse Nancy

Kinga Philipps
as Steve's Nurse

Joan Blair
as Moustache Lady

Katie Lohmann
as Centerfold

Diana Terranova
as Girl in Michael's Dream

Stephanie Chao
as Girl in Michael's Dream

Nikita Ager
as Girl in Michael's Dream

Kimberly Fisher
as Girl in Michael's Dream (uncredited)

Heather Ankeny
as Mistaken Natalie

Rachel Sterling
as Cherry

Shelby Stockton
as Mistaken Bride

Eric Gilliom
as Mistaken Groom

Jovanna Vitiello
as Stripper

Candice Michelle
as Stripper

Danielle Ciardi
as Stripper

Tre Temptor
as Male Stripper

Darcy Donavan
as Lifeguard (uncredited)

Scott Lincoln
as Homeless Man

Barry Sigismondi
as Chasing Cop

Joseph D. Reitman
as Carrot Lover

Sandra McCurdy
as Body double (uncredited)

Michelle Arthur
as Wedding Guest (uncredited)

Jesse Bernstein
as Poker Player (uncredited)

Bill Maher
as Carlos (uncredited)

Garry Marshall
as Uncle Murray (uncredited)

Emilio Rivera
as Sampson (uncredited)

Thomas Rosales Jr.
as Gang Member (uncredited)

Scott L. Schwartz
as Biker (uncredited)

Michael A. Tessiero
as High Roller (uncredited)
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