Movies Like Expensive Kisses

If you liked Expensive Kisses (1930), a comedy movie directed by William Watson, 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
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.
2
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.
3
Chris Rock: Never Scared (2004)
★ 7.5/10Also comedy
Chris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scared. Featuring his unique, insightful…
4
The Ladies Man (1961)
★ 6.3/10Also comedy
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…
5
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
6
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…
7
Easy Money (1983)
★ 6/10Also comedy
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
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
The Roast of Tom Brady (2024)
★ 6.7/10Also comedy
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
10
68 Kill (2017)
★ 5.9/10Also comedy
Chip's problem is that he can't say no to beautiful women. This weakness gets him into a world of trouble when he agrees to help his girlfriend steal $68,000.
11
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.
12
Held Up (1999)
★ 5.9/10Also comedy
What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the…
13
Yankee Zulu (1993)
★ 6.2/10Also comedy
Two South African boys, one white, Rhino, and one black, Zulu, go their separate ways after an incident. Many years later, they meet up again as adults, when one, after living for years in the United States, is now a…
14
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.
15
Take the Money and Run (1969)
★ 7.1/10Also comedy
Virgil Starkwell is intent on becoming a notorious bank robber. Unfortunately for Virgil and his not-so-budding career, he is completely incompetent.
16
72 HOURS (2026)
★ 6.8/10Also comedy
To save his career, a 40-year-old ad exec joins a crew of twentysomethings for a wild Miami bachelor party after they mistakenly add him to a group chat.
17
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.
18
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.
19
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!