Dynamic Watchlist Hub: Apr 12, 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
The Proposal

The Proposal

2009★ 7.1

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

When she learns she's in danger of losing her visa status and being deported, overbearing book editor Margaret Tate forces her put-upon assistant, Andrew Paxton, to marry her....

#2
Picture Perfect

Picture Perfect

1997★ 5.8

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

A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met....

#3
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....

#4
Hitch

Hitch

2005★ 6.6

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

Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own rom...

#5
Roman Holiday

Roman Holiday

1953★ 7.9

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

Overwhelmed by her suffocating schedule, touring European princess Ann takes off for a night while in Rome. When a sedative she took from her doctor kicks in, however, she falls as...

#6
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...

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