Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Try and Win

If you loved Try and 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 Try and Win.

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#1
Chris D'Elia: Incorrigible

Chris D'Elia: Incorrigible

2015★ 6.1

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

Comedian and actor Chris D’Elia, known for his dynamic physical comedy, explains why the NFL would be way more entertaining if it were real lions, bears and Vikings battling each o...

#2
The Wedding Year

The Wedding Year

2019★ 6.0

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

A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year....

#3
Bill Burr: Walk Your Way Out

Bill Burr: Walk Your Way Out

2017★ 6.9

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

No-nonsense comic Bill Burr takes the stage in Nashville and riffs on fast food, overpopulation, dictators and gorilla sign language....

#4
Donald Glover: Weirdo

Donald Glover: Weirdo

2012★ 6.8

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

Fearlessly funny stand-up comic and sitcom star Donald Glover puts on a live show in New York, confessing his love for Cocoa Puffs and Toys "R" Us....

#5
The Best Man Holiday

The Best Man Holiday

2013★ 6.5

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

When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited....

#6
Bill Burr: Why Do I Do This?

Bill Burr: Why Do I Do This?

2008★ 7.7

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

One of America's fastest-rising comedians, Bill Burr wields his razor-sharp wit with rare skill. In this brand-new stand-up performance, Bill takes aim at the stuff that drives us ...

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