Movies Like Two Jills and a Jack

If you liked Two Jills and a Jack (1947), a comedy movie directed by Jules White, 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
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.
2
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.
3
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
4
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.
5
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
6
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!
7
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.
8
Good Neighbor Sam (1964)
★ 6.6/10Also comedy
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral…
9
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
10
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.
11
Spa Weekend (2026)
★ 6.5/10Also comedy
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…
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
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.
14
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
15
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
16
Adam Sandler: Love You (2024)
★ 6.3/10Also comedy
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
17
Aziz Ansari: Intimate Moments for a Sensual Evening (2010)
★ 6.8/10Also comedy
Aziz Ansari presents his highly anticipated debut hour long stand-up special. The critically acclaimed stand-up and actor (Parks and Recreation, Funny People) discusses topics ranging from sheets with fraudulent thread…
18
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.
19
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.