Owen Wilson
Dupree
Kate Hudson
Molly
Matt Dillon
Carl
Michael Douglas
Mr. Thompson
Seth Rogen
Neil
Amanda Detmer
Annie
Ralph Ting
Toshi
Todd Stashwick
Tony
Bill Hader
Mark
Lance Armstrong
Lance Armstrong
Jason Winer
Eddie
Sidney S. Liufau
Paco
Billy Gardell
Bartender Dave
Eli Vargas
Aaron
Houston Mack
Dougie
Bob Larkin
Army Veteran
Suzanne Ford
Thompson's Secretary
Claudia Choi
Carl's Secretary
Summer Altice
Stripper
Jeanine Hass
Stripper
Peter Ruocco
Wedding Planner
Joe Russo
Personnel Manager
Lance Irwin
Neighborhood Father
Fenessa Pineda
2nd Grade Girl
Mario Revolori
2nd Grade Boy
Jay Lembeck
Minister
Gil Harris
Reese
Pat Crawford Brown
Aunt Kathy
Bayani Ison
Hawaiian Bartender
Joe Wilson
Joe
Blaine Pate
Larry
Kevin Breznahan
Charlie
Trevor Stock
Herb
Sean Perrone
Ned
Craig Hosking
Pilot
Harry Dean Stanton
Curly (uncredited)
Amber Hay
Wedding Guest (uncredited)
Kepa Kruse
Waiter (uncredited)
Michelle Lee
Hawaiian Air Ticketing Agent (uncredited)
May Porter
Waitress (uncredited)
Tasha Smith
Co-Worker (uncredited)