Gerry

Ben Mendelsohn

Acting

Curtis

Ryan Reynolds

Acting

Simone

Sienna Miller

Acting

Vanessa

Lio Tipton

Acting

Sam

Alfre Woodard

Acting

Tony Roundtree

James Toback

Writing

Dorothy

Robin Weigert

Acting

Louise

Yvonne Landry

Acting

Larry

Anthony Howard

Acting

Clifford

Jayson Warner Smith

Acting

Riverboat Waitress

Kerry Cahill

Acting

"Bloody Mary" Kate

Jane McNeill

Acting

Chuck Poker Dealer

Jason Shaffette

Acting

Dale

P.J. Marshall

Acting

Denise

Stephanie Honoré

Acting

Home Buying Wife

Teri Wyble

Acting

Home Buying Husband

Hunter Burke

Acting

Big Winner

Randy Austin

Acting

Skinny Thug

Jared Bankens

Acting

Waiter

Joshua Powell

Acting

Dealer

Tim Louie

Acting

Older Gentleman

Poland Perkins

Crew

Loser

Don Brady

Acting

Dennis' Dealer

Jay Cooper

Acting

Player One

Joshua Wilcox

Acting

Donna

Susan McPhail

Acting

Leo Welch

Leo 'Bud' Welch

Acting

Curvy Woman

Samantha Beaulieu

Acting

Dennis

Jason Davis

Acting

Man in Bar

Lucky Johnson

Acting

Local Bar Patron

Shamarr Allen

Acting

Dora

Indigo

Acting

Frat Boy

Wes Lagarde

Acting

Teller

Cheri Jones

Acting

Baller

Jamal Dennis

Acting

Pete

Thomas Francis Murphy

Acting

Cherry

Marshall Chapman

Acting

Roulette Croupier

Cheri Williams

Acting

Blackjack Dealer

Joshua Varmall

Acting

Craps Croupier

Joseph Blake Hollier

Acting

Steakhouse Waitress

Mary Patricia Seidel

Acting

Alice

Lauren Gros

Acting

Racetrack Patron (uncredited)

Chris Angerdina

Acting

Dog Track Patron (uncredited)

Aaron J. Brooks

Acting

High Roller (uncredited)

David Scott Gaudin

Acting

Pitboss (uncredited)

Justin Lebrun

Acting