Mississippi Grind

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

PJ 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

Thomas Francis Murphy

Pete

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)