Movies Like Moonlight Masquerade

If you liked Moonlight Masquerade (1942), a comedy movie directed by John H. Auer, 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
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.
2
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
3
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.
4
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
5
Chief Daddy 2: Going for Broke (2021)
★ 6/10Also comedy
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
Shadow of the Thin Man (1941)
★ 7/10Also comedy
While attending a major horse race with their young son, Nick Jr., Nick and Nora Charles witnesse a shocking murder from the crowded grandstand. What first appears to be an isolated killing soon leads to a maze of…
7
Fun with Dick and Jane (2005)
★ 6.2/10Also comedy
After Dick Harper loses his job at Globodyne in an Enron-esque collapse, he and his wife, Jane, turn to crime in order to handle the massive debt they now face. Two intelligent people, Dick and Jane actually get pretty…
8
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…
9
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
10
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!
11
Why Him? (2016)
★ 6.4/10Also comedy
A dad forms a bitter rivalry with his daughter's young rich boyfriend.
12
The Honey Pot (1967)
★ 6.5/10Also comedy
In Venice, a millionaire hires an actor to help him prank three greedy exes into thinking he's dying and leaving his fortune to one of them.
13
The In-Laws (1979)
★ 6.6/10Also comedy
In preparation for his daughter's wedding, dentist Sheldon Kornpett meets Vince Ricardo, the groom's father. Vince, a manic fellow who claims to be a government agent, then proceeds to drag Sheldon into a series of…
14
Switching Channels (1988)
★ 6.1/10Also comedy
A television news chief courts his anchorwoman ex-wife with an eleventh-hour story.
15
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
16
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…
17
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…
18
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
19
Song of the Thin Man (1947)
★ 6.7/10Also comedy
While attending a glamorous jazz cruise on New York’s East River, Nick and Nora Charles witness the fatal shooting of a wealthy patron. When suspicion falls on a young bandleader and his musicians, the couple steps in…
20
Cul-de-sac (1966)
★ 6.7/10Also comedy
On the run and in search of help, two wounded gangsters find refuge in the secluded castle of a feeble man and his wife; however, under the point of a gun, nothing is what it seems.