Movies Like The Kiss Of Debt

If you liked The Kiss Of Debt (2000), a comedy movie directed by Derek Diorio, 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
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.
2
Oscar (1991)
★ 6.4/10Also comedy
Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets…
3
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.
4
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.
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
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.
7
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…
8
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.
9
You're Never Too Young (1955)
★ 6.6/10Also comedy
When an aspiring barber becomes inadvertently involved in the theft of a valuable diamond, necessity forces him to masquerade as a 12 year-old child - with humorous consequences.
10
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.
11
Johnny Dangerously (1984)
★ 6.3/10Also comedy
An honest, goodhearted man is forced to turn to a life of crime to finance his neurotic mother's skyrocketing medical bills.
12
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
13
Gotcha! (1985)
★ 6/10Also comedy
A student on a trip to France is tricked into smuggling secrets across the Iron Curtain by a sexy spy.
14
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends escape to a luxury spa retreat to reconnect, unwind and rediscover themselves, but their weekend of relaxation soon turns into a series of wild adventures and bad decisions.
15
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!
16
The Ladykillers (2004)
★ 6.1/10Also comedy
An eccentric, if not charming Southern professor and his crew pose as a band in order to rob a casino, all under the nose of his unsuspecting landlord – a sharp old woman.
17
Ricky Gervais Live 2: Politics (2004)
★ 6.8/10Also comedy
A year after Animals, Ricky Gervais comes back with his second stand up comedy tour: Politics.
18
Chris Rock: Kill the Messenger (2008)
★ 7.6/10Also comedy
An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing…
19
The Million Pound Note (1954)
★ 7/10Also comedy
An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds. The sailor finds that whenever he…
20
Hostile Takeover (2025)
★ 6.9/10Also comedy
Follows Pete, a professional hitman, as he faces a group of assassins after the boss of a crime syndicate suspects disloyalty due to his attendance at Workaholics Anonymous meetings.