Movies Like To the Ladies

If you liked To the Ladies (1924), a comedy movie directed by James Cruze, here are 19 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
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.
2
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.
3
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.
4
Duplex (2003)
★ 6.1/10Also comedy
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!
5
The Three Stooges (2012)
★ 5.8/10Also comedy
Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…
6
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.
7
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
8
Accident Man (2018)
★ 6.3/10Also comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
9
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.
10
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…
11
The Willoughbys (2020)
★ 7.1/10Also comedy
When the four Willoughby children are abandoned by their selfish parents, they must learn how to adapt their Old-Fashioned values to the contemporary world in order to create something new: The Modern Family.
12
Seriously Single (2020)
★ 6.8/10Also comedy
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
13
I Love My Dad (2022)
★ 5.9/10Also comedy
A hopelessly estranged father catfishes his son in an attempt to reconnect.
14
Louis C.K.: Ridiculous (2026)
★ 6.1/10Also comedy
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
15
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
16
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.
17
Sneakerella (2022)
★ 5.9/10Also comedy
When El, an aspiring sneaker designer from Queens, meets Kira King, the fiercely independent daughter of legendary basketball star and sneaker tycoon Darius King, sparks fly as the two bond over their mutual affinity…
18
The Loud House Movie (2021)
★ 7.2/10Also comedy
The Loud family travel to Scotland and discover they are descendants of Scottish royalty as they move into their giant ancestral castle.
19
The Best Man Holiday (2013)
★ 6.5/10Also comedy
When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.