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
Anthony Howard
Larry
Jayson Warner Smith
Clifford
Kerry Cahill
Riverboat Waitress
Jane McNeill
"Bloody Mary" Kate
Jason Shaffette
Chuck Poker Dealer
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
Tim Louie
Dealer
Poland Perkins
Older Gentleman
Don Brady
Loser
Jay Cooper
Dennis' Dealer
Joshua Wilcox
Player One
Susan McPhail
Donna
Leo 'Bud' Welch
Leo Welch
Samantha Beaulieu
Curvy Woman
Jason Davis
Dennis
Lucky Johnson
Man in Bar
Shamarr Allen
Local Bar Patron
Indigo
Dora
Wes Lagarde
Frat Boy
Cheri Jones
Teller
Jamal Dennis
Baller
Marshall Chapman
Cherry
Cheri Williams
Roulette Croupier
Joshua Varmall
Blackjack Dealer
Joseph Blake Hollier
Craps Croupier
Mary Patricia Seidel
Steakhouse Waitress
Lauren Gros
Alice
Chris Angerdina
Racetrack Patron (uncredited)
Aaron J. Brooks
Dog Track Patron (uncredited)
David Scott Gaudin
High Roller (uncredited)
Justin Lebrun
Pitboss (uncredited)