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
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)
Anthony Howard
Larry
Jason Shaffette
Chuck Poker Dealer
Tim Louie
Dealer
Poland Perkins
Older Gentleman
Don Brady
Loser
Jay Cooper
Dennis' Dealer
Joshua Wilcox
Player One
Susan McPhail
Donna
Lucky Johnson
Man in Bar
Shamarr Allen
Local Bar Patron
Wes Lagarde
Frat Boy
Cheri Jones
Teller
Cheri Williams
Roulette Croupier
Joshua Varmall
Blackjack Dealer
Joseph Blake Hollier
Craps Croupier
Mary Patricia Seidel
Steakhouse Waitress
Chris Angerdina
Racetrack Patron (uncredited)
David Scott Gaudin
High Roller (uncredited)