Owen Wilson

Dupree

Kate Hudson

Molly

Matt Dillon

Carl

Michael Douglas

Mr. Thompson

Seth Rogen

Neil

Amanda Detmer

Annie

Todd Stashwick

Tony

Bill Hader

Mark

Lance Armstrong

Lance Armstrong

Jason Winer

Eddie

Sidney S. Liufau

Paco

Billy Gardell

Bartender Dave

Suzanne Ford

Thompson's Secretary

Claudia Choi

Carl's Secretary

Summer Altice

Stripper

Joe Russo

Personnel Manager

Fenessa Pineda

2nd Grade Girl

Mario Revolori

2nd Grade Boy

Gil Harris

Reese

Pat Crawford Brown

Aunt Kathy

Bayani Ison

Hawaiian Bartender

Kevin Breznahan

Charlie

Craig Hosking

Pilot

Harry Dean Stanton

Curly (uncredited)

Amber Hay

Wedding Guest (uncredited)

Michelle Lee

Hawaiian Air Ticketing Agent (uncredited)

Tasha Smith

Co-Worker (uncredited)