Alfre Woodard

Sam

Ryan Reynolds

Curtis

Lio Tipton

Vanessa

Sienna Miller

Simone

Ben Mendelsohn

Gerry

Don Brady

Loser

Randall Emmett

Executive Producer

Yvonne Landry

Louise

Ryan Fleck

Director

Anna Boden

Director

Robin Weigert

Dorothy

Stephanie Honoré

Denise

Teri Wyble

Home Buying Wife

Jane McNeill

"Bloody Mary" Kate

Jeremy Kipp Walker

Executive Producer

Kerry Cahill

Riverboat Waitress

James Toback

Tony Roundtree

Hunter Burke

Home Buying Husband

PJ Marshall

Dale

Jayson Warner Smith

Clifford

Jared Bankens

Skinny Thug

Randy Austin

Big Winner

Anthony Howard

Larry

Jason Shaffette

Chuck Poker Dealer

Joshua Powell

Waiter

Tim Louie

Dealer

Poland Perkins

Older Gentleman

Jay Cooper

Dennis' Dealer

John Lesher

Executive Producer