Once Upon a Time in the Midlands

Movies Like

Once Upon a Time in the Midlands (2002)

Romance, Comedy, Drama

If you loved Once Upon a Time in the Midlands, you'll love these similar films. Handpicked based on shared themes, genre, and feel.

Love Jones

Love Jones

1997 ★ 7.4

Darius Lovehall is a young black poet in Chicago who starts dating Nina Moseley, a beautiful and talented photographer. While trying to figure out if they've got a "love thing" or are just "kicking it," they hang out with their friends, talking about love and sex. Then Nina tests the strength of Darius' feelings and sets a chain of romantic complications into motion.

Dean

Dean

2016 ★ 5.8

A comedy about loss, grief, and the redemptive power of love. Dean is a NY illustrator who falls hard for an LA woman while trying to prevent his father from selling the family home in the wake of his mother's death.

The Giant Mechanical Man

The Giant Mechanical Man

2012 ★ 6.5

An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.

The Best You Can

The Best You Can

2025 ★ 7.0

Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.

Night Owls

Night Owls

2015 ★ 6.2

After workaholic Kevin has a drunken one night stand with the beautiful train-wreck Madeline, he's horrified to discover that she's actually his boss' jilted ex-mistress. When she takes a bottle of sleeping pills, Kevin is forced to keep her awake... and over the course of the night the two begin to fall for each other.

The Good House

The Good House

2021 ★ 6.2

Hildy Good, a wry New England realtor and descendant of the Salem witches who loves her wine and loves her secrets. Her compartmentalized life starts to unravel as she rekindles an old romance and becomes dangerously entwined in one person’s reckless behavior.

¿Quieres ser mi hijo?

¿Quieres ser mi hijo?

2023 ★ 8.4

Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.

Love & Sex

Love & Sex

2000 ★ 6.1

When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.

Jack Goes Boating

Jack Goes Boating

2010 ★ 6.0

A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.

How to Please a Woman

How to Please a Woman

2022 ★ 6.3

When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.

Greenberg

Greenberg

2010 ★ 5.9

Roger Greenberg, a failed musician now making a living as a carpenter in New York, returns to Los Angeles to house-sit for his brother. He's stranded there—since he doesn't drive—until his brother's assistant, Florence, comes to his rescue. She's as much a lost soul as he is, and the pair form a significant connection—giving Roger a much-needed reason to be happy.

Madame

Madame

2017 ★ 5.9

Anne and Bob, a well-to-do American couple, have just moved to a beautiful manor house in romantic Paris. To impress their sophisticated friends, they decide to host a lavish dinner party, but must disguise their maid as a noblewoman to even out the number of guests. When the maid runs off with a wealthy guest, Anne must chase her around Paris to thwart the joyous and unexpected love affair.

Endless

Endless

2020 ★ 6.7

When madly in love high school graduates Riley and Chris are separated by a tragic car accident, Riley blames herself for her boyfriend's death while Chris is stranded in limbo. Miraculously, the two find a way to connect. In a love story that transcends life and death, both Riley and Chris are forced to learn the hardest lesson of all: letting go.

The Elder Son

The Elder Son

2006 ★ 6.0

A thief on the run convinces a single father that he is his long-lost son. Complications ensue when he falls in love with his newfound "sister".

Puppy Love

Puppy Love

2023 ★ 7.0

After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are on the way! The hilariously mismatched Nicole and Max are forced to become responsible co-parents, but may end up finding love themselves.

Love Don't Co$t a Thing

Love Don't Co$t a Thing

2003 ★ 7.6

A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.

He Said, She Said

He Said, She Said

1991 ★ 5.9

Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.

XX/XY

XX/XY

2002 ★ 5.9

Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.

My Sassy Girl

My Sassy Girl

2008 ★ 6.7

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

Sitting in Bars with Cake

Sitting in Bars with Cake

2023 ★ 7.0

Extrovert Corinne convinces Jane, a shy, talented baker, to commit to a year of bringing cakes to bars, to help her meet people and build confidence. But when Corinne receives a life-altering diagnosis, the pair faces a challenge unlike anything they've experienced before.

Want AI-powered personalized recommendations?

Find Something to Watch