Win Win Cast
The cast of Win Win.
Paul Giamatti
as Mike Flaherty

Paul Giamatti plays the character of Mike Flaherty.

Alex Shaffer
as Kyle

Alex Shaffer portrays the character of Kyle.

Amy Ryan
as Jackie Flaherty

Amy Ryan embodies the role of Jackie Flaherty.

Melanie Lynskey
as Cindy Timmons

Melanie Lynskey portrays the character of Cindy Timmons.

Bobby Cannavale
as Terry Delfino

Bobby Cannavale plays the character of Terry Delfino.

Jeffrey Tambor
as Vigman

Jeffrey Tambor portrays the character of Vigman.

Burt Young
as Leo Poplar

Burt Young embodies the role of Leo Poplar.

Nina Arianda
as Shelly

Nina Arianda plays the character of Shelly.

Margo Martindale
as Eleanor
Clare Foley
as Abby
David Thompson
as Stemler
Marcia Haufrecht
as Gina Flaherty
Sharon Wilkins
as Judge Lee
Penelope Kindred
as Stella
Sophie Kindred
as Stella
Tim Ransom
as Stuart Thatcher
Marceline Hugot
as Woman Jogging
Darren Goldstein
as Sheffield Coach
Edmund Ikeda
as Frank
Joseph Tiboni
as Steve Deluca / Principal
Pam Levine
as Church Soloist
Dariusz M. Uczkowski
as Zachary Lowenstein
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