Movies Like The Sin of Harold Diddlebock

If you liked The Sin of Harold Diddlebock (1947), a comedy movie directed by Preston Sturges, 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 Mouse That Roared (1959)
★ 6.4/10Also comedy
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
2
At the Circus (1939)
★ 6.4/10Also comedy
Jeff Wilson, the owner of a small circus, owes his partner Carter $10,000. Before Jeff can pay, Carter's accomplices steal the money so he can take over the circus. Antonio Pirelli and Punchy, who work at the circus…
3
Rat Race (2001)
★ 6.3/10Also comedy
In an ensemble film about easy money, greed, manipulation and bad driving, a Las Vegas casino tycoon entertains his wealthiest high rollers -- a group that will bet on anything -- by pitting six ordinary people against…
4
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
5
Family Guy Presents: Blue Harvest (2007)
★ 7.4/10Also comedy
With the Griffins stuck at home during a blackout, Peter tells the story of "Star Wars Episode IV: A New Hope".
6
Monkey Business (1952)
★ 6.7/10Also comedy
Research chemist Barnaby Fulton works on a fountain of youth pill for a chemical company. One of the labs chimps gets loose in the laboratory and mixes chemicals, but then pours the mix into the water cooler. When…
7
Malibu Rescue: The Next Wave (2020)
★ 6.2/10Also comedy
It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on…
8
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.
9
She Done Him Wrong (1933)
★ 5.9/10Also comedy
New York singer and nightclub owner Lady Lou has more male friends than can be imagined. One is a vicious escaped criminal on the way to see 'his' girl, unaware she hasn't exactly been faithful in his absence. Help is…
10
Dennis the Menace (1993)
★ 5.9/10Also comedy
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam…
11
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
12
Hollywood or Bust (1956)
★ 6.2/10Also comedy
The last movie with Jerry Lewis and Dean Martin together, is a satire of the life in Hollywood. Steve Wiley is a deceiver who cheats Malcolm Smith when he wins a car, claiming that he won it too. Trying to steal the…
13
The Geisha Boy (1958)
★ 6.5/10Also comedy
Gilbert Wooley is a second-rate magician who is sent to entertain the troops in the pacific. During his time in Japan he becomes attached to a little orphan boy.
14
Johnny English Strikes Again (2018)
★ 6.3/10Also comedy
Disaster strikes when a criminal mastermind reveals the identities of all active undercover agents in Britain. The secret service can now rely on only one man - Johnny English. Currently teaching at a minor prep…
15
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
16
Stewie Griffin: The Untold Story (2005)
★ 6.9/10Also comedy
The maniacal baby of the Griffin family, Stewie, meets his future self. In doing this he discovers that his future image is not what he has anticipated because of a near death experience.
17
Take the Money and Run (1969)
★ 7.1/10Also comedy
Virgil Starkwell is intent on becoming a notorious bank robber. Unfortunately for Virgil and his not-so-budding career, he is completely incompetent.
18
Who's Minding the Store? (1963)
★ 6.8/10Also comedy
Norman Phiffer, a proud man in a humble life, doesn't know that his girlfriend, Barbara, is heir to the Tuttle Department Store dynasty. Mrs. Tuttle, Barbara's mother, is determined to split the two lovers, and hires…
19
A Song Is Born (1948)
★ 6.5/10Also comedy
The story of seven scholars in search of an expert to teach them about swing music. They seem to have found the perfect candidate in winsome nightclub singer Honey Swanson. But Honey's gangster boyfriend doesn't want…
20
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.