Movies Like Once Upon a Time in the Midlands

If you liked Once Upon a Time in the Midlands (2002), a romance and comedy movie directed by Shane Meadows, 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
Love Jones (1997)
★ 7.4/10Also comedy and drama
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…
2
Why Did I Get Married Again? (2026)
★ 6.8/10Also comedy and romance
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"
3
The Best You Can (2025)
★ 7/10Also comedy and romance
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…
4
Love & Sex (2000)
★ 6.2/10Also comedy and drama
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…
5
Voicemails for Isabelle (2026)
★ 8.3/10Also romance and comedy
A young woman's hilariously confessional voicemails to her late sister are unknowingly redirected to a stranger, who begins to fall in love from afar.
6
¿Quieres ser mi hijo? (2023)
★ 8.4/10Also comedy and romance
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.
7
How to Please a Woman (2022)
★ 6.3/10Also romance and comedy
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.
8
Father of the Bride (1950)
★ 7/10Also comedy and romance
Proud father Stanley Banks remembers the day his daughter, Kay, got married. Starting when she announces her engagement through to the wedding itself, we learn of all the surprises and disasters along the way.
9
The Right Kind of Wrong (2013)
★ 5.9/10Also romance and comedy
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
10
Cover Girl (1944)
★ 6.4/10Also comedy and romance
A nightclub dancer makes it big in modeling, leaving her dancer boyfriend behind.
11
He Said, She Said (1991)
★ 5.9/10Also comedy and drama
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…
12
Love Don't Co$t a Thing (2003)
★ 7.7/10Also comedy and drama
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.
13
Sex and Death 101 (2007)
★ 6.2/10Also comedy and romance
A guy's life is turned around by an email, which includes the names of everyone he's had sex with and ever will have sex with. His situation gets worse when he encounters a femme fatale who targets men guilty of sex…
14
XX/XY (2002)
★ 6/10Also drama and comedy
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
15
Sitting in Bars with Cake (2023)
★ 7/10Also romance and comedy
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…
16
Cyrus (2010)
★ 5.9/10Also comedy and drama
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before…
17
Puppy Love (2023)
★ 7/10Also comedy and romance
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…
18
Newness (2017)
★ 6.1/10Also romance and drama
In contemporary Los Angeles, two millennials navigating a social media–driven hookup culture begin a relationship that pushes both emotional and physical boundaries.
19
Dirty Sexy Saint (2019)
★ 6.3/10Also romance and drama
Clay Kincaid hates the nickname 'Saint', he got for being too kind to stray animals and desperate people. Especially when it comes to women. With a rough and damaged past that has left him jaded, he doesn't do…
20
A Star Is Born (1976)
★ 6/10Also drama and romance
Has-been singing idol John Norman Howard falls in love with young, up-and-coming songstress Esther Hoffman in Frank Pierson's version of the classic love story updated to the rock and roll era.