Movies like The High Cost of Loving (1958)
The best movies like The High Cost of Loving (1958) are Fun with Dick and Jane (1977), The Errand Boy (1961) and Held Up (1999). If The High Cost of Loving hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedEddie Murphy Raw (1987)7.2/10 from 395 votes
- NewestDriver's Ed (2026)Released 2026
Fun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Errand Boy (1961)
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 ever finds is that he can cause havoc no matter what he does.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHeld Up (1999)
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 local Sip and Zip.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Trouble with Angels (1966)
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 their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBabes (2024)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Distinguished Gentleman (1992)
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 from lobbyists.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisEddie Murphy Raw (1987)
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisClass Rank (2017)
Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisOld Dads (2023)
A cranky middle-aged dad and his two best friends find themselves out of step in a changing world of millennial CEOs and powerful preschool principals.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAmerican Dreamer (2022)
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.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisDriver's Ed (2026)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisEasy Money (1983)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: Armageddon (2023)
Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDuplex (2003)
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!
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisNo Time for Sergeants (1958)
Georgia farm boy Will Stockdale is about to bust with pride. He’s been drafted. Will’s ready. But is Uncle Sam ready for Will?
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisSextuplets (2019)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGeorge Carlin: It's Bad for Ya! (2008)
It's Bad For Ya, Carlin's Emmy nominated 14th and final HBO special from March of 2008 features Carlin's noted irreverent and unapologetic observations on topics ranging from death, religion, bureaucracy, patriotism, overprotected children and big business to the pungent examinations of modern language and the decrepit state of the American culture.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisMe Time (2022)
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Roast of Tom Brady (2024)
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCarry On Regardless (1961)
After a bunch of no-hopers approaches an employment agency, the anarchy mounts as they do a series of odd jobs, including a chimp's tea party, trying to stay sober at a wine tasting… and demolishing a house.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like The High Cost of Loving?
The closest matches to The High Cost of Loving are Fun with Dick and Jane (1977), The Errand Boy (1961) and Held Up (1999). Below are 17 more, each with the reason it matches.
What should I watch after The High Cost of Loving?
Start with Fun with Dick and Jane (1977), the closest match to The High Cost of Loving.
What is the highest-rated movie like The High Cost of Loving?
Eddie Murphy Raw (1987), rated 7.2/10 by 395 TMDB users.
What is the newest movie like The High Cost of Loving?
Driver's Ed (2026) is the most recent release on this list.
Are there English movies like The High Cost of Loving?
Yes: Fun with Dick and Jane (1977), The Errand Boy (1961) and Held Up (1999).
How are movies similar to The High Cost of Loving chosen?
First come films that Trakt’s viewers watch alongside The High Cost of Loving, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.