Dynamic Watchlist Hub: May 14, 2026

10 Best Movies Like How To Kill a Playboy

If you loved How To Kill a Playboy, 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 Kill a Playboy.

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#1
American Dreamer

American Dreamer

2022★ 5.8

Why watch this? A perfect follow-up to How To Kill a Playboy 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
Dave Chappelle: The Unstoppable...

Dave Chappelle: The Unstoppable...

2025★ 6.6

Why watch this? A perfect follow-up to How To Kill a Playboy 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....

#3
Noises Off...

Noises Off...

1992★ 7.1

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

Hired to helm an Americanized take on a British play, director Lloyd Fellowes does his best to control an eccentric group of stage actors. With a star actress quickly passing her p...

#4
Held Up

Held Up

1999★ 5.8

Why watch this? A perfect follow-up to How To Kill a Playboy 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...

#5
El Sinvergüenza

El Sinvergüenza

1983★ 7.8

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

Married man hires a surrogate to pose as the father of the four children he has had with his mistress....

#6
Puff, Puff, Pass

Puff, Puff, Pass

2006★ 5.8

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

Danny Masterson (TV's 'That '70s Show') leads a hilarious ensemble cast in a tale about two hapless stoners who get involved in a scheme to rip off a shady character named Mr. Big ...

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