Win Win

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

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