Win Win

Win Win Cast

Ranked by Wikipedia Pageviews · January 29, 2026
1
Bobby Cannavaleas Terry Delfino
5,844
2
Melanie Lynskeyas Cindy Timmons
4,884
3
Paul Giamattias Mike Flaherty
2,820
4
Jeffrey Tamboras Vigman
1,946
5
Amy Ryanas Jackie Flaherty
1,876
6
Margo Martindaleas Eleanor
1,337
7
Burt Youngas Leo Poplar
1,002
8
Nina Ariandaas Shelly
699
9
Marceline Hugotas Woman Jogging
108
10
Darren Goldsteinas Sheffield Coach
107
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Win Win Full Cast

All 22 cast members with Wikipedia pageview rankings
PG
Paul Giamatti
as Mike Flaherty
Rank #2,0082,820 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 #3,2931,876 daily views

Amy Ryan embodies the role of Jackie Flaherty.

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ML
Melanie Lynskey
as Cindy Timmons
Rank #8734,884 daily views

Melanie Lynskey portrays the character of Cindy Timmons.

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BC
Bobby Cannavale
as Terry Delfino
Rank #6405,844 daily views

Bobby Cannavale plays the character of Terry Delfino.

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JT
Jeffrey Tambor
as Vigman
Rank #3,1641,946 daily views

Jeffrey Tambor portrays the character of Vigman.

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BY
Burt Young
as Leo Poplar
Rank #5,9631,002 daily views

Burt Young embodies the role of Leo Poplar.

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NA
Nina Arianda
as Shelly
Rank #7,912699 daily views

Nina Arianda plays the character of Shelly.

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MM
Margo Martindale
as Eleanor
Rank #4,6761,337 daily views
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CF
Clare Foley
as Abby
Rank #22,68184 daily views
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DT
David Thompson
as Stemler
Rank #23,59274 daily views
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MH
Marcia Haufrecht
as Gina Flaherty
Rank #35,2928 daily views
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SW
Sharon Wilkins
as Judge Lee
Rank #28,36836 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 #20,840108 daily views
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DG
Darren Goldstein
as Sheffield Coach
Rank #20,912107 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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