Win Win

Paul Giamatti

Mike Flaherty

Amy Ryan

Jackie Flaherty

Bobby Cannavale

Terry Delfino

Jeffrey Tambor

Vigman

Burt Young

Leo Poplar

Melanie Lynskey

Cindy Timmons

Alex Shaffer

Kyle

Margo Martindale

Eleanor

David Thompson

Stemler

Nina Arianda

Shelly

Mike Diliello

Jimmy Reed

Marcia Haufrecht

Gina Flaherty

Sharon Wilkins

Judge Lee

Clare Foley

Abby

Penelope Kindred

Stella

Sophie Kindred

Stella

Tim Ransom

Stuart Thatcher

Nicholas Somers

BHS Coach

Jacqueline Brogan

Woman Jogging

Marceline Hugot

Woman Jogging

Edmund Ikeda

Frank

Joseph Tiboni

Steve Deluca / Principal

Pam Levine

Church Soloist

Darren Goldstein

Sheffield Coach