Dynamic Watchlist Hub: Apr 18, 2026

10 Best Movies Like How Bill Squared It with His Boss

If you loved How Bill Squared It with His 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 How Bill Squared It with His Boss.

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#1
Watching the Detectives

Watching the Detectives

2007★ 6.3

Why watch this? A perfect follow-up to How Bill Squared It with His 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...

#2
Taking Care of Business

Taking Care of Business

1990★ 6.3

Why watch this? A perfect follow-up to How Bill Squared It with His Boss 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....

#3
Girl on a Bicycle

Girl on a Bicycle

2013★ 6.0

Why watch this? A perfect follow-up to How Bill Squared It with His Boss for fans of Comedy. It captures a similar light-hearted atmosphere.

Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French wo...

#4
Wicked Little Letters

Wicked Little Letters

2024★ 6.9

Why watch this? A perfect follow-up to How Bill Squared It with His Boss for fans of Comedy. It captures a similar light-hearted atmosphere.

When the denizens of Littlehampton – including conservative Edith – begin receiving letters full of hilarious profanities, rowdy Irish migrant Rose is charged with the crime. Suspe...

#5
Let's Make Love

Let's Make Love

1960★ 6.4

Why watch this? A perfect follow-up to How Bill Squared It with His 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...

#6
Why Worry?

Why Worry?

1923★ 6.5

Why watch this? A perfect follow-up to How Bill Squared It with His Boss 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....

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