Dynamic Watchlist Hub: Apr 13, 2026

10 Best Movies Like The Winning Five

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

🏆

Expert Review & Ratings

See our full critical analysis and audience score for The Winning Five.

View Review →
Advertisement
#1
The Hangover Part III

The Hangover Part III

2013★ 6.2

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

This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off....

#2
The Kissing Booth 3

The Kissing Booth 3

2021★ 6.9

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

It’s the summer before Elle heads to college, and she has a secret decision to make. Elle has been accepted into Harvard, where boyfriend Noah is matriculating, and also Berkeley, ...

#3
Class

Class

1983★ 5.9

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

Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is embo...

#4
Why Worry?

Why Worry?

1923★ 6.5

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

A hypochondriac vacations in the tropics for the fresh air - and finds himself in the middle of a revolution instead....

#5
The Wedding Year

The Wedding Year

2019★ 6.0

Why watch this? A perfect follow-up to The Winning Five 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....

#6
Life of the Party

Life of the Party

2018★ 6.1

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

When her husband suddenly dumps her, longtime dedicated housewife Deanna turns regret into re-set by going back to college... landing in the same class and school as her daughter, ...

Advertisement