Win Win - Cast

Paul Giamatti

Mike Flaherty
Actor

Amy Ryan

Jackie Flaherty
Actor

Bobby Cannavale

Terry Delfino
Actor

Jeffrey Tambor

Vigman
Actor

Burt Young

Leo Poplar
Actor

Melanie Lynskey

Cindy Timmons
Actor

Alex Shaffer

Kyle
Actor

Margo Martindale

Eleanor
Actor

David Thompson

Stemler
Actor

Nina Arianda

Shelly
Actor

Marcia Haufrecht

Gina Flaherty
Actor

Sharon Wilkins

Judge Lee
Actor

Clare Foley

Abby
Actor

Penelope Kindred

Stella
Actor

Sophie Kindred

Stella
Actor

Tim Ransom

Stuart Thatcher
Actor

Marceline Hugot

Woman Jogging
Actor

Edmund Ikeda

Frank
Actor

Joseph Tiboni

Steve Deluca / Principal
Actor

Pam Levine

Church Soloist
Actor

Darren Goldstein

Sheffield Coach
Actor

Dariusz M. Uczkowski

Zachary Lowenstein
Actor

Emma Degerstedt

Miss Durrance (uncredited)
Actor

Joanna Theobalds

Gina (uncredited)
Actor

Tom McArdle

Wrestling Match Announcer (uncredited)
Actor

Cliff Moylan

Contractor (uncredited)
Actor