Ben Mendelsohn

Gerry

Ryan Reynolds

Curtis

Sienna Miller

Simone

Lio Tipton

Vanessa

Alfre Woodard

Sam

James Toback

Tony Roundtree

Robin Weigert

Dorothy

Yvonne Landry

Louise

Jayson Warner Smith

Clifford

Kerry Cahill

Riverboat Waitress

Jane McNeill

"Bloody Mary" Kate

P.J. Marshall

Dale

Stephanie Honoré

Denise

Teri Wyble

Home Buying Wife

Hunter Burke

Home Buying Husband

Randy Austin

Big Winner

Jared Bankens

Skinny Thug

Joshua Powell

Waiter

Leo 'Bud' Welch

Leo Welch

Samantha Beaulieu

Curvy Woman

Jason Davis

Dennis

Lucky Johnson

Man in Bar

Indigo

Dora

Jamal Dennis

Baller

Thomas Francis Murphy

Pete

Marshall Chapman

Cherry

Lauren Gros

Alice

Aaron J. Brooks

Dog Track Patron (uncredited)

Justin Lebrun

Pitboss (uncredited)