Movies Like Gildersleeve on Broadway

If you liked Gildersleeve on Broadway (1943), a comedy movie directed by Gordon Douglas, 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
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.
2
A Burlesque on Carmen (1915)
★ 5.8/10Also comedy
A gypsy seductress is sent to sway a goofy officer to allow a smuggling run.
3
Black Sheep (1996)
★ 6.1/10Also comedy
When dignified Albert Donnelly runs for Governor, his team moves to keep his slow-witted and klutzy younger brother, Mike, out of the eye of the media. To baby-sit Mike, the campaign assigns sarcastic Steve, who gets…
4
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…
5
The Apple Dumpling Gang (1975)
★ 6.6/10Also comedy
A roving bachelor gets saddled with three children and a wealth of trouble when the youngsters stumble upon a huge gold nugget. They join forces with two bumbling outlaws to fend off the greedy townspeople and soon…
6
Support Your Local Gunfighter (1971)
★ 6.6/10Also comedy
A con artist arrives in a mining town controlled by two competing companies. Both companies think he's a famous gunfighter and try to hire him to drive the other out of town.
7
The Ladies Man (1961)
★ 6.3/10Also comedy
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
8
The Trouble with Angels (1966)
★ 6.7/10Also comedy
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and…
9
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…
10
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
11
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.
12
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.
13
Go West (1940)
★ 6.6/10Also comedy
A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.
14
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
15
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.
16
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…
17
The Ladykillers (1955)
★ 7.3/10Also comedy
Five oddball criminals planning a bank robbery rent rooms on a cul-de-sac from an octogenarian widow under the pretext that they are classical musicians.
18
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
19
Sherlock Jr. (1924)
★ 8/10Also comedy
A film projectionist longs to be a detective, and puts his meager skills to work when he is framed by a rival for stealing his girlfriend's father's pocketwatch.
20
Oliver the Eighth (1934)
★ 7.1/10Also comedy
Barbershop owners Stan and Ollie answer an ad in the newspaper from a wealthy widow looking for a husband. Ollie only mails in his response and is invited to the widow's mansion. Stan discovers his unmailed letter and…