Dynamic Watchlist Hub: May 11, 2026

10 Best Movies Like My Boss

If you loved My 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 My Boss.

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#1
Housesitter

Housesitter

1992★ 6.1

Why watch this? A perfect follow-up to My Boss for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Con artist Gwen moves into Newton's empty home without his knowledge and begins setting up house, posing as his new wife....

#2
One Small Hitch

One Small Hitch

2013★ 6.6

Why watch this? A perfect follow-up to My Boss for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

On a flight home to Chicago for a family wedding, childhood friends Josh and Molly innocently agree to fake a wedding engagement to make Josh's dying father happy. Things quickly g...

#3
Only You

Only You

1994★ 6.7

Why watch this? A perfect follow-up to My Boss for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Two childhood paranormal incidents have convinced schoolteacher Faith Corvatch that her true love is a guy named 'Damon Bradley', but she has yet to meet him. Preparing to marry po...

#4
What a Way to Go!

What a Way to Go!

1964★ 7.1

Why watch this? A perfect follow-up to My Boss for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

A four-time widow discusses her four marriages, in which all of her husbands became incredibly rich and died prematurely because of their drive to be rich....

#5
This Little Love of Mine

This Little Love of Mine

2021★ 6.1

Why watch this? A perfect follow-up to My Boss for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Laura Price is a successful San Francisco lawyer on the cusp of promotion – a far cry from her childhood growing up on a tropical island with best friends Chip and Gem. When the fi...

#6
Easy Virtue

Easy Virtue

2008★ 6.4

Why watch this? A perfect follow-up to My Boss for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness...

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