Movies Like To Dorothy, a Son

If you liked To Dorothy, a Son (1954), a comedy movie directed by Muriel Box, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
How to Make a Killing (2026)
★ 6.9/10Also comedy
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
Blank Check (1994)
★ 6/10Also comedy
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 when a money-laundering criminal…
3
Big Business (1988)
★ 6.4/10Also comedy
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 rich family just passing through. The…
4
Greedy (1994)
★ 6.2/10Also comedy
Meet the McTeagues. They've come to stake a claim in their wealthy uncle's will… only he's not dead yet!
5
Why Him? (2016)
★ 6.4/10Also comedy
A dad forms a bitter rivalry with his daughter's young rich boyfriend.
6
The Family Jewels (1965)
★ 6.5/10Also comedy
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.
7
Delivery Man (2013)
★ 6.3/10Also comedy
An affable underachiever finds out he's fathered 533 children through anonymous donations to a fertility clinic 20 years ago. Now he must decide whether or not to come forward when 142 of them file a lawsuit to reveal…
8
Yankee Zulu (1993)
★ 6.2/10Also comedy
Two South African boys, one white, Rhino, and one black, Zulu, go their separate ways after an incident. Many years later, they meet up again as adults, when one, after living for years in the United States, is now a…
9
Brewster's Millions (1985)
★ 6.6/10Also comedy
Monty Brewster, an aging minor-league baseball player, stands to inherit $300 million if he can successfully spend $30 million in 30 days without anything to show for it, and without telling anyone what he's up to... A…
10
Father of the Bride (1991)
★ 6.5/10Also comedy
George Banks is an ordinary, middle-class man whose 22 year-old daughter Annie has decided to marry a man from an upper-class family, but George can't think of what life would be like without his daughter. His wife…
11
3 Men and a Little Lady (1990)
★ 5.8/10Also comedy
Sylvia's work increasingly takes her away from the three men who help bring up Mary, her daughter. When she decides to move to England and take Mary with her, the three men are heartbroken at losing the two most…
12
Good Neighbor Sam (1964)
★ 6.6/10Also comedy
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral…
13
The Phoenician Scheme (2025)
★ 6.5/10Also comedy
Wealthy businessman Zsa-zsa Korda appoints his only daughter, a nun, as sole heir to his estate. As Korda embarks on a new enterprise, they soon become the target of scheming tycoons, foreign terrorists, and determined…
14
Queenpins (2021)
★ 6.5/10Also comedy
Bored and frustrated suburban homemaker Connie and her best pal JoJo, a vlogger with dreams, turn a hobby into a multi-million-dollar counterfeit coupon caper. After firing off a letter to the conglomerate behind a box…
15
The Fortune Cookie (1966)
★ 7.2/10Also comedy
TV cameraman Harry Hinkle is injured while filming a football game. Seeing big dollar signs, his unscrupulous ambulance-chasing lawyer brother-in-law Willie Gingrich enters the picture, and convinces Harry to overstate…
16
This Is 40 (2012)
★ 5.9/10Also comedy
Pete and Debbie are both about to turn 40, their kids hate each other, both of their businesses are failing, they're on the verge of losing their house, and their relationship is threatening to fall apart.
17
She-Devil (1989)
★ 6/10Also comedy
A cunning and resourceful housewife vows revenge on her husband when he begins an affair with a wealthy romance novelist.
18
Easy Money (1983)
★ 6/10Also comedy
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
19
I'll Be Home for Christmas (1998)
★ 6/10Also comedy
Estranged from his father, college student Jake is lured home to New York for Christmas with the promise of receiving a classic Porsche as a gift. When the bullying football team dumps him in the desert in a Santa…
20
Switching Channels (1988)
★ 6/10Also comedy
A television news chief courts his anchorwoman ex-wife with an eleventh-hour story.