Dynamic Watchlist Hub: May 12, 2026

10 Best Movies Like How to Be Miserable and Enjoy It

If you loved How to Be Miserable and Enjoy It, 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 Be Miserable and Enjoy It.

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#1
American Dreamer

American Dreamer

2022★ 5.8

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

In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy...

#2
The Ladies Man

The Ladies Man

1961★ 6.3

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

After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women...

#3
Held Up

Held Up

1999★ 5.8

Why watch this? A perfect follow-up to How to Be Miserable and Enjoy It 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...

#4
Class Rank

Class Rank

2017★ 6.9

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

Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn ...

#5
So Much Love to Give

So Much Love to Give

2020★ 5.9

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

A bigamist with one family in Buenos Aires and the other in Mar del Plata sees his life turned upside down when his wives discover what he has hidden from them for so many years an...

#6
Thunderstruck

Thunderstruck

2012★ 6.1

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

After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an imp...

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