Dynamic Watchlist Hub: Apr 14, 2026

10 Best Movies Like A Pain in the Pullman

If you loved A Pain in the Pullman, 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 A Pain in the Pullman.

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#1
Let's Make Love

Let's Make Love

1960★ 6.4

Why watch this? A perfect follow-up to A Pain in the Pullman for fans of Comedy. It captures a similar light-hearted atmosphere.

When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful...

#2
Chris Rock: Tamborine

Chris Rock: Tamborine

2018★ 6.4

Why watch this? A perfect follow-up to A Pain in the Pullman for fans of Comedy. It captures a similar light-hearted atmosphere.

Chris Rock takes the stage for his first comedy special in 10 years, filled with searing observations on fatherhood, infidelity and American politics....

#3
Taking Care of Business

Taking Care of Business

1990★ 6.3

Why watch this? A perfect follow-up to A Pain in the Pullman for fans of Comedy. It captures a similar light-hearted atmosphere.

An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him....

#4
Fun with Dick and Jane

Fun with Dick and Jane

1977★ 6.5

Why watch this? A perfect follow-up to A Pain in the Pullman for fans of Comedy. It captures a similar light-hearted atmosphere.

When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation....

#5
Watching the Detectives

Watching the Detectives

2007★ 6.3

Why watch this? A perfect follow-up to A Pain in the Pullman for fans of Comedy. It captures a similar light-hearted atmosphere.

Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life fem...

#6
Dave Chappelle: Deep in the Heart of Texas

Dave Chappelle: Deep in the Heart of Texas

2017★ 7.6

Why watch this? A perfect follow-up to A Pain in the Pullman for fans of Comedy. It captures a similar light-hearted atmosphere.

Comedy icon Dave Chappelle makes his triumphant return to the screen with a pair of blistering, fresh stand-up specials. Filmed at the Moody Theater in Austin, Texas, in April 2015...

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