Win Win

Alex Shaffer as Kyle Bobby Cannavale as Terry Delfino Burt Young as Leo Poplar Tim Ransom as Stuart Thatcher Marceline Hugot as Woman Jogging Edmund Ikeda as Frank Joseph Tiboni as Steve Deluca / Principal Pam Levine as Church Soloist Paul Giamatti as Mike Flaherty Jeffrey Tambor as Vigman David Thompson as Stemler Sharon Wilkins as Judge Lee Sophie Kindred as Stella Penelope Kindred as Stella Amy Ryan as Jackie Flaherty Nina Arianda as Shelly Margo Martindale as Eleanor Clare Foley as Abby Marcia Haufrecht as Gina Flaherty Dariusz M. Uczkowski as Zachary Lowenstein Melanie Lynskey as Cindy Timmons Darren Goldstein as Sheffield Coach

Tom McArdle Editor Oliver Bokelberg Director of Photography Lisa Maria Falcone Producer Amanda Carroll Set Decoration Lyle Workman Original Music Composer Mary Jane Skalski Producer John Paino Production Design Michael London Producer Tom McCarthy Writer, Director, Screenplay, Producer Melissa Toth Costume Design Peter Bucossi Stunt Coordinator