Movies like Oh Mary Be Careful (1921)
The best movies like Oh Mary Be Careful (1921) are The Trouble with Angels (1966), My Wife's Relations (1922) and Police (1916). If Oh Mary Be Careful hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Gold Rush (1925)8.0/10 from 1,935 votes
- NewestSpa Weekend (2026)Released 2026
The Trouble with Angels (1966)
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 their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMy Wife's Relations (1922)
Buster and a woman are mistakenly married and her initially unfriendly family begins to treat him nicely when they come to believe he has a large inheritance awaiting him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisPolice (1916)
Charlie is released from prison and immediately swindled by a fake parson. A fellow ex-convict convinces Charlie to help burglarize a house.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisWhy Worry? (1923)
A hypochondriac vacations in the tropics for the fresh air - and finds himself in the middle of a revolution instead.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisFrom Soup to Nuts (1928)
Inexperienced waiters (Laurel & Hardy) are hired for a swank dinner party.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Chaplin Revue (1959)
Three Chaplin silent comedies "A Dog's Life", "Shoulder Arms", and "The Pilgrim" are strung together to form a single feature length film. Chaplin provides new music, narration, and a small amount of new connecting material. "Shoulder Arms" is now described as taking place in a time before "the atom bomb".
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisConvict 13 (1920)
A young golfer is mugged by an escaped convict and finds himself in a prison where he foils a jailbreak.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Woman (1915)
Mother, father and daughter go to the park. The women doze off on a bench while the father plays a hide-and-seek game with a girl, blindfolded. Charlie leads him into a lake. Both dozing ladies on the bench fall for Charlie and invite him for dinner. The father returns home with a friend. Charlie rushes upstairs and dresses like a woman, shaving his mustache. Both men fall for Charlie.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMuch Ado About Nothing (2013)
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShanghaied (1915)
A shipowner intends to scuttle his ship on its last voyage to get the insurance money. Charlie, a tramp in love with the owner's daughter, is grabbed by the captain and promises to help him shanghai some seamen. The daughter stows away to follow Charlie. Charlie assists in the galley and attempts to serve food during a gale.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Happiest Days of Your Life (1950)
Nutbourne College, an old established, all-boys, boarding school is told that another school is to be billeted with due to wartime restrictions. The shock is that it's an all-girls school that has been sent. The two head teachers are soon battling for the upper hand with each other and the Ministry. But a crisis (or two) forces them to work together.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Errand Boy (1961)
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty ever finds is that he can cause havoc no matter what he does.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDuplex (2003)
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Night in the Show (1915)
Two disruptive theater patrons, the wealthy drunk Mr. Pest (played by Charlie Chaplin) and the rowdy working-class Mr. Rowdy (also played by Chaplin), attend a live vaudeville theater production. Their constant antics, seat-hopping, and physical altercations quickly overshadow the acts on stage and plunge the entire theater into absolutely hilarious chaos.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLiberty (1929)
While changing clothes in a getaway car, escaped convicts Stan and Ollie mistakenly put on each other's pants. They spend the rest of the film trying to exchange pants in various unlikely settings.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSpa Weekend (2026)
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break, the women escape to a luxury spa retreat for an unforgettable weekend dedicated to fun, laughter, and a lot of really bad decisions.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Wedding Year (2019)
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.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Ladies Man (1961)
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 all these females?
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDough and Dynamite (1914)
Pierre and Jacques are working as waiters at a restaurant where the cooks go on strike. When the two are forced to work as bakers, the striking cooks put dynamite in the dough, with explosive results.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShane Gillis: Beautiful Dogs (2023)
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe General (1926)
During America’s Civil War, Union spies steal engineer Johnnie Gray's beloved locomotive, 'The General'—with Johnnie's lady love aboard an attached boxcar—and he single-handedly must do all in his power to both get The General back and to rescue Annabelle.
Why it matches: Similar story and style · both comedy
Absolute CinemaMovies like thisThe Gold Rush (1925)
A gold prospector in Alaska struggles to survive the elements and win the heart of a dance hall girl.
Why it matches: Similar story and style · both comedy
Absolute CinemaMovies like thisThe Rink (1916)
After amusements working in a restaurant, a waiter uses his lunch break to go roller skating.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Pawnshop (1916)
A pawnbroker's assistant deals with his grumpy boss, his annoying co-worker and some eccentric customers as he flirts with the pawnbroker's daughter, until a perfidious crook with bad intentions arrives at the pawnshop.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisString Beans (1918)
Farmer Toby Watkinsm whose fanciful poetry does not impress his exasperated uncle, leaves the farm to become a subscription solicitor for the "Sawbert Weekly Clarion." In Sawbert, Toby meets Mayor Lot Morris' daughter Jean, and the shy young people fall in love. Crooked stock promoter Kendall Reeves arrives in town and unveils his plan to open a string-bean cannery.
Why it matches: Similar story and style · both comedy
Un monsieur qui a mangé du taureau (1909)
At a dinner party, a hostess serves her guests a dish made using meat from a bull. While most of them enjoy the meal, one man has a strange reaction: Taking a set of horns off the wall, he attaches them to his head and sets off on a rampage. After destroying the house and terrifying his hostess, her guests, maid, and neighbours, he takes to the streets. The police sends a telegraph to Spain asking for help, and in response a parade of matadors arrive in Paris, ready to slay the crazy beast-man. However, soon after the man-bull fight begins, the errant guest comes to his senses and is taken into custody by waiting policemen.
Why it matches: Similar story and style · both comedy
The Janitor's Tea Party (1907)
The scene of the drama is a block of modern flats. Many of the residents are away at a dance, and the janitor and his staff decide upon a jollification of their own. They invite their friends to a fine high tea. Everybody is having a fine time, and their spirits are running high. We are now taken to the outside of the hall door, and watch with amusement the frantic pounding and bell ringing of the residents returning from their evening engagements and seeking admission to their apartments. The gay gathering inside are too busy with their own pleasure to heed the angry crowd outdoors. A policeman is called, but all to no purpose, and the tenants are all taken to the station for quarters for the night. Returning to the janitor's quarters we see that the jollifications have been concluded and the guests are all departing. The superior officer at the station concludes to make another effort to gain admittance in the building and, with the tenants at his heels, he approaches the flats.
Why it matches: Similar story and style · both comedy
The Day After (1909)
Mr. and Mrs. Hilton throw a New Year's Eve party. They agree not to drink the punch themselves, but as guests begin to arrive their resolve weakens, and soon they are both cavorting drunkenly. Next morning Mr. Hilton, feeling very sick, is conscience-stricken over his drunkenness and his behavior with another woman. He fears to face his wife until he discovers that she feels just as guilty herself.
Why it matches: Similar story and style · both comedy
Romance of a Boot and a Dancing Slipper (1909)
Romance of a Boot and a Dancing Slipper
Why it matches: Similar story and style · both comedy
His Grace’s Will (1919)
A series of family entanglements develop around the changing will of Roger Bernhuses de Sars, who wants his heritage to go to his illegitimate daughter Blenda. But love and fate also plays their cards.
Why it matches: Similar story and style · both comedy
Like Oh Mary Be Careful and something else?
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Frequently asked questions
What are the best movies like Oh Mary Be Careful?
The closest matches to Oh Mary Be Careful are The Trouble with Angels (1966), My Wife's Relations (1922) and Police (1916). Below are 27 more, each with the reason it matches.
What should I watch after Oh Mary Be Careful?
Start with The Trouble with Angels (1966), the closest match to Oh Mary Be Careful.
What is the highest-rated movie like Oh Mary Be Careful?
The Gold Rush (1925), rated 8.0/10 by 1,935 TMDB users.
What is the newest movie like Oh Mary Be Careful?
Spa Weekend (2026) is the most recent release on this list.
Are there English movies like Oh Mary Be Careful?
Yes: The Trouble with Angels (1966), My Wife's Relations (1922) and Police (1916).
How are movies similar to Oh Mary Be Careful chosen?
First come films that Trakt’s viewers watch alongside Oh Mary Be Careful, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.