Dynamic Watchlist Hub: May 18, 2026

10 Best Movies Like To Dorothy, a Son

If you loved To Dorothy, a Son, 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 To Dorothy, a Son.

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#1
How to Make a Killing

How to Make a Killing

2026★ 7.1

Why watch this? A perfect follow-up to To Dorothy, a Son for fans of Comedy. It captures a similar light-hearted atmosphere.

Disowned at birth by his obscenely wealthy family, blue-collar Becket Redfellow will stop at nothing to reclaim his inheritance, no matter how many relatives stand in his way....

#2
Big Business

Big Business

1988★ 6.4

Why watch this? A perfect follow-up to To Dorothy, a Son for fans of Comedy. It captures a similar light-hearted atmosphere.

In the 1940s in the small town of Jupiter Hollow, two sets of identical twins are born in the same hospital on the same night. One set to a poor local family and the other to a ric...

#3
The Family Jewels

The Family Jewels

1965★ 6.5

Why watch this? A perfect follow-up to To Dorothy, a Son for fans of Comedy. It captures a similar light-hearted atmosphere.

A young heiress must choose between six uncles, one of which is up to no good and out to harm the girl's beloved bodyguard who practically raised her....

#4
Blank Check

Blank Check

1994★ 6.0

Why watch this? A perfect follow-up to To Dorothy, a Son for fans of Comedy. It captures a similar light-hearted atmosphere.

Bullied by his siblings and nagged by his parents, 11-year-old Preston Waters is fed up with his family — especially their frugality. But he gets his chance to teach them a lesson ...

#5
Chief Daddy 2: Going for Broke

Chief Daddy 2: Going for Broke

2021★ 6.0

Why watch this? A perfect follow-up to To Dorothy, a Son for fans of Comedy. It captures a similar light-hearted atmosphere.

The Beecroft family are ready to spend all of Chief Daddy's inheritance, but not if the CEO of his company has anything to do with it....

#6
Why Him?

Why Him?

2016★ 6.4

Why watch this? A perfect follow-up to To Dorothy, a Son for fans of Comedy. It captures a similar light-hearted atmosphere.

A dad forms a bitter rivalry with his daughter's young rich boyfriend....

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