Movies Like Lillian's Dilemma

If you liked Lillian's Dilemma (1914), a comedy movie directed by Wilfrid North, 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
A Night at the Opera (1935)
★ 7.4/10Also comedy
The Marx Brothers take on high society and the opera world to bring two lovers together. A sly business manager and two wacky friends of two opera singers help them achieve success while humiliating their stuffy and…
2
A Woman (1915)
★ 6.1/10Also comedy
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…
3
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
4
A-Haunting We Will Go (1942)
★ 6.2/10Also comedy
Stan and Ollie get involved with con men, crooks, a genial magician, and two interchangeable coffins with disastrous but funny results.
5
Ladies First (2026)
★ 6/10Also comedy
An arrogant but charismatic ladies' man finds his life of money, power and casual flings upended when he wakes up in a parallel world dominated by women.
6
Dough and Dynamite (1914)
★ 6.1/10Also comedy
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.
7
LEGO Marvel Avengers: Mission Demolition (2024)
★ 6.5/10Also comedy
A young, aspiring hero and superhero fan inadvertently unleashes a powerful new villain looking to rid the world of the Avengers.
8
Thunderstruck (2012)
★ 6.2/10Also comedy
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
9
Hard Luck (1921)
★ 6.9/10Also comedy
A down on his luck young man makes several attempts at committing suicide but fails them too. He then finds himself becoming more confident through a series of petty adventures, to such an extent that this becomes his…
10
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.
11
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…
12
The Railrodder (1965)
★ 6.8/10Also comedy
After literally swimming across the Atlantic Ocean, an Englishman takes a country trip across Canada on a railcar.
13
Gotcha! (1985)
★ 6/10Also comedy
A student on a trip to France is tricked into smuggling secrets across the Iron Curtain by a sexy spy.
14
London Calling (2025)
★ 6.4/10Also comedy
After fleeing the UK from a job gone wrong, a down on his luck hitman is forced to babysit the son of his new crime boss and show him how to become a man.
15
Marvel One-Shot: All Hail the King (2014)
★ 6.8/10Also comedy
A documentary filmmaker interviews the now-famous Trevor Slattery from behind bars.
16
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
17
Shanghaied (1915)
★ 6/10Also comedy
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…
18
Cruella (2021)
★ 8/10Also comedy
In 1970s London amidst the punk rock revolution, a young grifter named Estella is determined to make a name for herself with her designs. She befriends a pair of young thieves who appreciate her appetite for mischief…
19
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.
20
The Bank (1915)
★ 6.3/10Also comedy
A janitor at a bank is in love with a secretary and dreams that she has fallen in love with him too.