Win Win

Win Win Cast

Ranked by Wikipedia Pageviews · February 18, 2026
1
Bobby Cannavaleas Terry Delfino
7,956
2
Melanie Lynskeyas Cindy Timmons
4,932
3
Paul Giamattias Mike Flaherty
3,045
4
Jeffrey Tamboras Vigman
1,976
5
Amy Ryanas Jackie Flaherty
1,728
6
Margo Martindaleas Eleanor
1,501
7
Burt Youngas Leo Poplar
1,050
8
Nina Ariandaas Shelly
692
9
Marceline Hugotas Woman Jogging
108
10
David Thompsonas Stemler
96
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Win Win Full Cast

All 22 cast members with Wikipedia pageview rankings
PG
Paul Giamatti
as Mike Flaherty
Rank #1,8623,045 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 #3,6681,728 daily views

Amy Ryan embodies the role of Jackie Flaherty.

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ML
Melanie Lynskey
as Cindy Timmons
Rank #9124,932 daily views

Melanie Lynskey portrays the character of Cindy Timmons.

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BC
Bobby Cannavale
as Terry Delfino
Rank #3877,956 daily views

Bobby Cannavale plays the character of Terry Delfino.

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JT
Jeffrey Tambor
as Vigman
Rank #3,1471,976 daily views

Jeffrey Tambor portrays the character of Vigman.

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BY
Burt Young
as Leo Poplar
Rank #5,8321,050 daily views

Burt Young embodies the role of Leo Poplar.

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NA
Nina Arianda
as Shelly
Rank #8,011692 daily views

Nina Arianda plays the character of Shelly.

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MM
Margo Martindale
as Eleanor
Rank #4,2331,501 daily views
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CF
Clare Foley
as Abby
Rank #22,27389 daily views
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DT
David Thompson
as Stemler
Rank #21,73796 daily views
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MH
Marcia Haufrecht
as Gina Flaherty
Rank #37,3824 daily views
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SW
Sharon Wilkins
as Judge Lee
Rank #28,25937 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 #20,881108 daily views
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DG
Darren Goldstein
as Sheffield Coach
Rank #23,05980 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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