Movies Like The Opposite of Cleveland

If you liked The Opposite of Cleveland (2019), a movie directed by Dan Chaimowitz, 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
The Back-Up Plan (2010)
★ 6.1/10
When Zoe tires of looking for Mr. Right, she decides to have a baby on her own. But on the day she's artificially inseminated, she meets Stan, who seems to be just who she's been searching for all her life. Now, Zoe…
2
She's Funny That Way (2015)
★ 5.9/10
On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.
3
Don Jon (2013)
★ 6/10
A New Jersey guy dedicated to his family, friends, and church, develops unrealistic expectations from watching porn and works to find happiness and intimacy with his potential true love.
4
Send Me No Flowers (1964)
★ 6.8/10
When a hypochondriac assumes that he is dying, he makes an elaborate plan to ensure his wife's happiness. However, trouble ensues when she misunderstands his intentions.
5
Alfie (2004)
★ 5.9/10
A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.
6
Sleuth (2007)
★ 6.3/10
Locked in a high-tech English manor, bound in a deadly duel of wits, Andrew Wyke and Milo Tindle come together as English gentlemen to discuss the matter of Wyke's wife: the woman both are sleeping with.
7
The Switch (2010)
★ 6.2/10
Kassie is a smart, fun-loving single woman who, despite her neurotic best friend Wally’s objections, decides it’s time to have a baby – even if it means doing it herself… with a little help from a charming sperm donor…
8
My Awkward Sexual Adventure (2012)
★ 6.7/10
A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he'll help her with her crushing debt if she helps him become a better lover.
9
For Love or Money (1993)
★ 6.2/10
New York concierge Doug Ireland wants to go into business for himself and refurbish a hotel on Roosevelt Island, N.Y., but he needs an investor. With a few weeks left before his option on the site runs out, Doug agrees…
10
Down with Love (2003)
★ 6.1/10
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.
11
The Love Hypothesis (2026)
★ 7.9/10
Olive Smith, a biology PhD candidate, and Dr. Adam Carlsen, a hotshot professor and well-known tyrant, enter into a fake relationship, seeing each of their carefully calculated theories on love get thrown into chaos.
12
Two Weeks Notice (2002)
★ 6.4/10
Dedicated environmental lawyer Lucy Kelson goes to work for billionaire George Wade as part of a deal to preserve a community center. Indecisive and weak-willed George grows dependent on Lucy's guidance on everything…
13
The Woman in Red (1984)
★ 6.3/10
When a happily married family man, who would never consider an affair, meets a beautiful woman in red, he is totally infatuated and desperate to make her acquaintance. However, as he tries out various schemes to sneak…
14
Locke (2014)
★ 6.9/10
Ivan Locke has worked hard to craft a good life for himself. Tonight, that life will collapse around him. On the eve of the biggest challenge of his career, Ivan receives a phone call that sets in motion a series of…
15
Fifty Shades of Grey (2015)
★ 5.9/10
When college senior Anastasia Steele steps in for her sick roommate to interview prominent businessman Christian Grey for their campus paper, little does she realize the path her life will take. Christian, as enigmatic…
16
The Assessment (2025)
★ 6.8/10
In a climate change-ravaged world, a utopian society optimizes life, including parenthood assessments. A successful couple faces scrutiny by an evaluator over seven days to determine their fitness for childbearing.
17
52 Pick-Up (1986)
★ 6.1/10
Harry Mitchell is a successful Los Angeles manufacturer whose wife is running for city council. His life is turned upside down when three blackmailers confront him with a videotape of him with his young mistress and…
18
There's Something About Mary (1998)
★ 6.6/10
For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy…
19
50 First Dates (2004)
★ 6.9/10
Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and…
20
Electric Dreams (1984)
★ 6.4/10
Miles Harding buys a state-of-the-art computer that starts expressing conscious thought and emotion after an interaction with spilled champagne. Things begin getting out of hand when both Miles and Edgar, the computer…