Ben Mendelsohn as Gerry

Ryan Reynolds as Curtis

Sienna Miller as Simone

Lio Tipton as Vanessa

Alfre Woodard as Sam

James Toback as Tony Roundtree

Robin Weigert as Dorothy

Yvonne Landry as Louise

Anthony Howard as Larry

Jayson Warner Smith as Clifford

Kerry Cahill as Riverboat Waitress

Jane McNeill as "Bloody Mary" Kate

Jason Shaffette as Chuck Poker Dealer

P.J. Marshall as Dale

Stephanie Honoré as Denise

Teri Wyble as Home Buying Wife

Hunter Burke as Home Buying Husband

Randy Austin as Big Winner

Jared Bankens as Skinny Thug

Joshua Powell as Waiter

Tim Louie as Dealer

Poland Perkins as Older Gentleman

Don Brady as Loser

Jay Cooper as Dennis' Dealer

Joshua Wilcox as Player One

Susan McPhail as Donna

Leo 'Bud' Welch as Leo Welch

Samantha Beaulieu as Curvy Woman

Jason Davis as Dennis

Lucky Johnson as Man in Bar

Shamarr Allen as Local Bar Patron

Indigo as Dora

Wes Lagarde as Frat Boy

Cheri Jones as Teller

Jamal Dennis as Baller

Thomas Francis Murphy as Pete

Marshall Chapman as Cherry

Cheri Williams as Roulette Croupier

Joshua Varmall as Blackjack Dealer

Joseph Blake Hollier as Craps Croupier

Mary Patricia Seidel as Steakhouse Waitress

Lauren Gros as Alice

Chris Angerdina as Racetrack Patron (uncredited)

Aaron J. Brooks as Dog Track Patron (uncredited)

David Scott Gaudin as High Roller (uncredited)

Justin Lebrun as Pitboss (uncredited)