Win Win

Win Win Cast

Ranked by Wikipedia Pageviews · April 01, 2026
1
Bobby Cannavaleas Terry Delfino
7,254
2
Melanie Lynskeyas Cindy Timmons
3,342
3
Paul Giamattias Mike Flaherty
2,133
4
Jeffrey Tamboras Vigman
1,886
5
Margo Martindaleas Eleanor
1,739
6
Amy Ryanas Jackie Flaherty
1,673
7
Burt Youngas Leo Poplar
798
8
Nina Ariandaas Shelly
430
9
Darren Goldsteinas Sheffield Coach
111
10
Clare Foleyas Abby
97
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Win Win Full Cast

All 22 cast members with Wikipedia pageview rankings
PG
Paul Giamatti
as Mike Flaherty
Rank #2,5332,133 daily views

Paul Giamatti plays the character of Mike Flaherty.

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AS
Alex Shaffer
as Kyle

Alex Shaffer portrays the character of Kyle.

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AR
Amy Ryan
as Jackie Flaherty
Rank #3,3941,673 daily views

Amy Ryan embodies the role of Jackie Flaherty.

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ML
Melanie Lynskey
as Cindy Timmons
Rank #1,3613,342 daily views

Melanie Lynskey portrays the character of Cindy Timmons.

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BC
Bobby Cannavale
as Terry Delfino
Rank #3597,254 daily views

Bobby Cannavale plays the character of Terry Delfino.

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JT
Jeffrey Tambor
as Vigman
Rank #2,9331,886 daily views

Jeffrey Tambor portrays the character of Vigman.

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BY
Burt Young
as Leo Poplar
Rank #6,769798 daily views

Burt Young embodies the role of Leo Poplar.

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NA
Nina Arianda
as Shelly
Rank #10,496430 daily views

Nina Arianda plays the character of Shelly.

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MM
Margo Martindale
as Eleanor
Rank #3,2481,739 daily views
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CF
Clare Foley
as Abby
Rank #21,23697 daily views
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DT
David Thompson
as Stemler
Rank #23,50571 daily views
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MH
Marcia Haufrecht
as Gina Flaherty
Rank #37,5234 daily views
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SW
Sharon Wilkins
as Judge Lee
Rank #31,59420 daily views
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PK
Penelope Kindred
as Stella
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SK
Sophie Kindred
as Stella
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TR
Tim Ransom
as Stuart Thatcher
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MH
Marceline Hugot
as Woman Jogging
Rank #23,50571 daily views
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DG
Darren Goldstein
as Sheffield Coach
Rank #20,166111 daily views
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EI
Edmund Ikeda
as Frank
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JT
Joseph Tiboni
as Steve Deluca / Principal
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PL
Pam Levine
as Church Soloist
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DU
Dariusz M. Uczkowski
as Zachary Lowenstein
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