Win Win

Win Win Cast

Ranked by Wikipedia Pageviews · March 30, 2026
1
Bobby Cannavaleas Terry Delfino
11,083
2
Melanie Lynskeyas Cindy Timmons
3,847
3
Paul Giamattias Mike Flaherty
2,867
4
Jeffrey Tamboras Vigman
2,557
5
Amy Ryanas Jackie Flaherty
2,160
6
Margo Martindaleas Eleanor
2,021
7
Burt Youngas Leo Poplar
1,329
8
Nina Ariandaas Shelly
435
9
Darren Goldsteinas Sheffield Coach
258
10
Clare Foleyas Abby
113
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Win Win Full Cast

All 22 cast members with Wikipedia pageview rankings
PG
Paul Giamatti
as Mike Flaherty
Rank #2,3402,867 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 #3,2522,160 daily views

Amy Ryan embodies the role of Jackie Flaherty.

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ML
Melanie Lynskey
as Cindy Timmons
Rank #1,5843,847 daily views

Melanie Lynskey portrays the character of Cindy Timmons.

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BC
Bobby Cannavale
as Terry Delfino
Rank #20511,083 daily views

Bobby Cannavale plays the character of Terry Delfino.

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JT
Jeffrey Tambor
as Vigman
Rank #2,6952,557 daily views

Jeffrey Tambor portrays the character of Vigman.

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BY
Burt Young
as Leo Poplar
Rank #5,2951,329 daily views

Burt Young embodies the role of Leo Poplar.

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NA
Nina Arianda
as Shelly
Rank #11,672435 daily views

Nina Arianda plays the character of Shelly.

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MM
Margo Martindale
as Eleanor
Rank #3,5272,021 daily views
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CF
Clare Foley
as Abby
Rank #21,414113 daily views
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DT
David Thompson
as Stemler
Rank #21,996104 daily views
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MH
Marcia Haufrecht
as Gina Flaherty
Rank #33,43815 daily views
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SW
Sharon Wilkins
as Judge Lee
Rank #29,62733 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 #22,72694 daily views
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DG
Darren Goldstein
as Sheffield Coach
Rank #15,367258 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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