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