Dynamic Watchlist Hub: May 17, 2026

10 Best Movies Like How to Win

If you loved How to 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 How to Win.

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#1
Held Up

Held Up

1999★ 5.8

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

What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is...

#2
LaRoy, Texas

LaRoy, Texas

2024★ 6.9

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

Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRo...

#3
Ricky Gervais Live 2: Politics

Ricky Gervais Live 2: Politics

2004★ 6.9

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

A year after Animals, Ricky Gervais comes back with his second stand up comedy tour: Politics....

#4
The F**k-It List

The F**k-It List

2020★ 6.0

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

After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can....

#5
Dave Chappelle: The Unstoppable...

Dave Chappelle: The Unstoppable...

2025★ 6.7

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

Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special....

#6
Eddie Murphy Raw

Eddie Murphy Raw

1987★ 7.3

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

Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more....

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