Movies Like High Maintenance

If you liked High Maintenance (2011), a comedy movie directed by Shawn Wines, 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
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…
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
The Flying Car (2002)
★ 6.7/10Also comedy
Stuck in a traffic jam, Dante and Randal discuss the prospect of a flying car.
4
The Trouble with Angels (1966)
★ 6.7/10Also comedy
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and…
5
The Family Jewels (1965)
★ 6.5/10Also comedy
A young heiress must choose between six uncles, one of which is up to no good and out to harm the girl's beloved bodyguard who practically raised her.
6
Monkey Business (1952)
★ 6.7/10Also comedy
Research chemist Barnaby Fulton works on a fountain of youth pill for a chemical company. One of the labs chimps gets loose in the laboratory and mixes chemicals, but then pours the mix into the water cooler. When…
7
Joe's Apartment (1996)
★ 5.8/10Also comedy
A nice guy has just moved to New York and discovers that he must share his run-down apartment with a couple thousand singing, dancing cockroaches.
8
Mickey's House of Villains (2002)
★ 7.3/10Also comedy
The villains from the popular animated Disney films are gathered at the House of Mouse with plans to take over. Soon, the villains take over the house and kick out Mickey, Donald and Goofy. It's all up to Mickey and…
9
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
10
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.
11
Support Your Local Gunfighter (1971)
★ 6.6/10Also comedy
A con artist arrives in a mining town controlled by two competing companies. Both companies think he's a famous gunfighter and try to hire him to drive the other out of town.
12
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.
13
The Thin Man Goes Home (1944)
★ 7.1/10Also comedy
Hoping for a peaceful visit with his parents in the small town of Sycamore Springs, Nick Charles and his wife Nora soon find themselves surrounded by old rivalries, family tensions, and a mysterious murder. Nick’s…
14
Family Guy Presents: Blue Harvest (2007)
★ 7.4/10Also comedy
With the Griffins stuck at home during a blackout, Peter tells the story of "Star Wars Episode IV: A New Hope".
15
LaRoy, Texas (2024)
★ 6.8/10Also comedy
Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.
16
The Errand Boy (1961)
★ 6.2/10Also comedy
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty…
17
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…
18
Robot Chicken: Star Wars (2007)
★ 7.2/10Also comedy
A series of 30 sketches, following the hilarious antics of various characters from a galaxy, far, far away.
19
Woody Woodpecker (2017)
★ 6.6/10Also comedy
Woody Woodpecker enters a turf war with a big city lawyer wanting to tear down his home in an effort to build a house to flip.
20
Magnum Opus (2022)
★ 7.2/10Also comedy
Groot sets out to paint a family portrait of himself and the Guardians, only to discover just how messy the artistic process can be.