Movies Like Head Over Bills

If you liked Head Over Bills (2022), a movie directed by Dabby Chimere, 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
Inventing the Abbotts (1997)
★ 6.3/10
In the 1950s, brothers Jacey and Doug Holt, who come from the poorer side of their sleepy Midwestern town, vie for the affections of the wealthy, lovely Abbott sisters. Lady-killer Jacey alternates between Eleanor and…
2
The Forge (2024)
★ 8.2/10
19 year old Isaiah Wright lives for basketball and video games. A year out of high school, he has no job, no plans, and no idea how to be a man. At odds with his single mother Cynthia, Isaiah is given an ultimatum – to…
3
Sense and Sensibility (2026)
★ 7.4/10
A charming, witty, and deeply relatable story of love and sisterhood.
4
The Virgin Suicides (2000)
★ 7.1/10
A group of male friends become obsessed with five mysterious sisters who are sheltered by their strict, religious parents.
5
Wasp (2003)
★ 7.2/10
Zoë is a single mother who lives with her four children in Dartford. She is poor and can't afford to buy food. One day her old flame drives by and asks her to go on a date with him. Scared that he doesn't want to go…
6
Bastard Out of Carolina (1996)
★ 7.1/10
A poor, struggling South Carolinian mother and daughter face painful choices with their resolve and pride. Bone, the eldest daughter, and Anney her tired mother, grow both closer and farther apart: Anney sees Glen as…
7
The Trouble with Angels (1966)
★ 6.7/10
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…
8
Moxie (2021)
★ 7.2/10
Inspired by her mom's rebellious past and a confident new friend, a shy 16-year-old publishes an anonymous zine calling out sexism at her school.
9
12 Feet Deep (2018)
★ 6/10
Two sisters are trapped under the fiberglass cover of an Olympic sized public pool and must brave the cold and each other to survive the harrowing night.
10
Where’s Poppa? (1970)
★ 6/10
When New York attorney Gordon Hocheiser meets Louise Callan, the girl of his dreams, he schemes to eliminate his aging, senile mother, even though he promised his late father that he'd always take care of her. He fears…
11
The Lost Daughter (2021)
★ 6.4/10
A woman's seaside vacation takes a dark turn when her obsession with a young mother forces her to confront secrets from her past.
12
Bride & Prejudice (2004)
★ 6.5/10
Mrs. Bakshi is eager to find suitors for her four unmarried daughters when a family friend introduces them to handsome American Will Darcy. A Bollywood-style modern adaptation of Jane Austen's classic novel.
13
The Girl in the Book (2015)
★ 5.8/10
The story of a young writer's transformation when her past invades her present.
14
Only the Lonely (1991)
★ 6.2/10
Danny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna, whose father owns the local funeral parlour. Naturally, his mother objects to the…
15
To All the Boys I've Loved Before (2018)
★ 7.6/10
Lara Jean's love life goes from imaginary to out of control when her secret letters to every boy she's ever fallen for are mysteriously mailed out.
16
Lovely & Amazing (2002)
★ 6.1/10
An intimate family portrait of four hapless but resilient women and the bittersweet lessons they learn in keeping up with the hectic demands of their individual neuroses. Each of the women seeks redemption in her own…
17
The Map That Leads to You (2025)
★ 6.7/10
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life…
18
Lorelei (2020)
★ 6/10
A man is released from prison after 15 years. He reunites with his high school girlfriend, now a single mother of three. What follows is a lyrical take on love, regret and second chances.
19
Overboard (1987)
★ 6.9/10
Heiress Joanna Stayton hires carpenter Dean Proffitt to build a closet on her yacht—and refuses to pay him for the project when it's done. But after Joanna accidentally falls overboard and loses her memory, Dean sees…
20
The Best of Me (2014)
★ 7.5/10
A pair of former high school sweethearts reunite after many years when they return to visit their small hometown.