Dynamic Watchlist Hub: Apr 13, 2026

10 Best Movies Like Today We're Playing Boss

If you loved Today We're Playing Boss, 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 Today We're Playing Boss.

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#1
American Dreamer

American Dreamer

2022★ 5.8

Why watch this? A perfect follow-up to Today We're Playing Boss 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
Let's Make Love

Let's Make Love

1960★ 6.4

Why watch this? A perfect follow-up to Today We're Playing Boss 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...

#3
Class Rank

Class Rank

2017★ 6.9

Why watch this? A perfect follow-up to Today We're Playing Boss 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 ...

#4
Watching the Detectives

Watching the Detectives

2007★ 6.3

Why watch this? A perfect follow-up to Today We're Playing Boss 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...

#5
In the Soup

In the Soup

1992★ 6.6

Why watch this? A perfect follow-up to Today We're Playing Boss for fans of Comedy. It captures a similar light-hearted atmosphere.

An aspiring young filmmaker gets involved with an eccentric gangster for the financing of his first film....

#6
Brain Donors

Brain Donors

1992★ 6.1

Why watch this? A perfect follow-up to Today We're Playing Boss for fans of Comedy. It captures a similar light-hearted atmosphere.

Three manic idiots—a lawyer, a cab driver and a handyman—team up to run a ballet company to fulfil the will of a millionaire. Stooge-like antics result as the trio try to outwit th...

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