Movies Like It Was in May

If you liked It Was in May (1915), a comedy movie directed by Victor Sjöström, 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
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.
2
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
3
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
4
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
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.
5
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.
6
The Fixer Uppers (1935)
★ 6.8/10Also comedy
Stan and Ollie are greeting card salesmen who agree to help a woman put a spark in her loveless marriage by making her husband jealous.
7
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.
8
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
9
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.
10
Perfect Day (1929)
★ 7/10Also comedy
Two families embark on a pleasant Sunday picnic but manage to run into a variety of issues with their temperamental automobile. Each incident requires repeated exits and reboardings by Laurel, Hardy, their wives and…
11
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.
12
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.
13
The Tramp (1915)
★ 6.5/10Also comedy
The Little Fellow finds the girl of his dreams and work on a family farm. He helps defend the farm against criminals, and all seems well, until he discovers the girl of his dreams already has someone in her life…
14
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!
15
Pretty Persuasion (2005)
★ 5.8/10Also comedy
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
16
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.
17
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
18
Dave Chappelle: The Dreamer (2023)
★ 6.9/10Also comedy
From his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.
19
Our Wife (1931)
★ 7.1/10Also comedy
Oliver is making plans to marry his sweetheart Dulcy with Stan as his best man, but the plans are thwarted when Dulcy's father sees a picture of Ollie and forbids the marriage. The couple plan to elope, and run away to…
20
Sea Scouts (1939)
★ 6.4/10Also comedy
Donald is an admiral on a seagoing voyage with his nephews in which they encounter a ravenous shark.