Dynamic Watchlist Hub: Jan 20, 2026

10 Best Movies Like Win Win

If you loved Win Win, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Win Win.

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#1
The Yes Men Fix the World

The Yes Men Fix the World

2009★ 7.0

Why watch this? A perfect follow-up to Win Win for fans of Documentary. It captures a similar compelling atmosphere.

THE YES MEN FIX THE WORLD is a screwball true story about two gonzo political activists who, posing as top executives of giant corporations, lie their way into big business confere...

#2
Sidney

Sidney

2022★ 7.6

Why watch this? A perfect follow-up to Win Win for fans of Documentary. It captures a similar compelling atmosphere.

This revealing documentary honors the legendary Sidney Poitier—iconic actor, filmmaker, and civil rights activist. Featuring interviews with Denzel Washington, Spike Lee, Halle Ber...

#3
An Invisible Sign

An Invisible Sign

2010★ 5.2

Why watch this? A perfect follow-up to Win Win for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

Mona Gray is a 20-year-old loner who, as a child, turned to math for salvation after her father became ill. As an adult, Mona now teaches the subject and must help her students thr...

#4
Point Blank

Point Blank

1967★ 7.0

Why watch this? A perfect follow-up to Win Win for fans of Drama. It captures a similar emotionally gripping atmosphere.

After being double-crossed and left for dead, a mysterious man named Walker single-mindedly tries to retrieve the rather inconsequential sum of money that was stolen from him....

#5
I Am Cuba

I Am Cuba

1964★ 7.8

Why watch this? A perfect follow-up to Win Win for fans of Drama. It captures a similar emotionally gripping atmosphere.

Four vignettes on the lives of the Cuban people in the pre-revolutionary era. In Havana, Maria is ashamed when a man she loves discovers how she makes a living. Pedro, an old farme...

#6
Your Sister's Sister

Your Sister's Sister

2011★ 6.5

Why watch this? A perfect follow-up to Win Win for fans of Comedy. It captures a similar light-hearted atmosphere.

Iris invites her friend Jack to stay at her family's island getaway after the death of his brother. At their remote cabin, Jack's drunken encounter with Hannah, Iris' sister, kicks...