Movies Like The Island of Love

If you liked The Island of Love (1960), a comedy movie directed by Kostas Karagiannis, 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
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
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.
3
Mr. Bones (2001)
★ 6/10Also comedy
A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.
4
Simpsley (2026)
★ 8.2/10Also comedy
When penniless con-artist Marge Bouvier is sent to Italy to convince wealthy sap Seymour Skinner to come home, she's tempted by the trappings of his affluent lifestyle. But there’s a big fat fly in the ointment…
5
The Distinguished Gentleman (1992)
★ 6/10Also comedy
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows…
6
Trailer Park Boys: Don't Legalize It (2014)
★ 6.4/10Also comedy
Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty…
7
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.
8
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
9
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.
10
The Air Up There (1994)
★ 6.1/10Also comedy
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home…
11
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…
12
Trailer Park Boys: Countdown to Liquor Day (2009)
★ 6.6/10Also comedy
Ricky, Julian and Bubbles are about to get out of jail, and this time, Julian vows to go straight, even open a legit business. Soon the Boys will all be rich. At least that's what they've told the parole board. But…
13
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.
14
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.
15
A Bad Idea Gone Wrong (2017)
★ 6.4/10Also comedy
Two would-be thieves forge a surprising relationship with an unexpected housesitter when they accidentally trap themselves in a house they just broke into.
16
Big Stan (2007)
★ 6.6/10Also comedy
A weak con man panics when he learns he's going to prison for fraud. He hires a mysterious martial arts guru who helps transform him into a martial arts expert who can fight off inmates who want to hurt or love him.
17
One Night at McCool's (2001)
★ 5.9/10Also comedy
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
18
Go West (1940)
★ 6.6/10Also comedy
A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.
19
Malibu Rescue: The Next Wave (2020)
★ 6.2/10Also comedy
It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on…
20
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.