Movies Like Oliver's Summer

If you liked Oliver's Summer (2021), a movie directed by Robert Boggs, 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
Barely Legal (2003)
★ 5.9/10
Teenager Deacon works at a video shop, and his buddies, Fred and Matt, sell the bootleg porno films he acquires. Deacon gets fired, but the pals have the bright idea of filming their own Internet porn flick in order to…
2
Two Moon Junction (1988)
★ 6.1/10
A young Southern débutante temporarily abandons her posh lifestyle and upcoming, semi-arranged marriage to have a lustful and erotic fling with a rugged drifter who works at a local carnival.
3
America: The Motion Picture (2021)
★ 5.8/10
A chainsaw-wielding George Washington teams with beer-loving bro Sam Adams to take down the Brits in a tongue-in-cheek riff on the American Revolution.
4
Cars Toon Mater's Tall Tales (2008)
★ 7.1/10
Mater the tow truck travels from country to country as he retells his infamous but unbelievable stories.
5
Winter Spring Summer or Fall (2024)
★ 7.3/10
Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.
6
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.
7
Shame (2011)
★ 6.9/10
Brandon, a thirty-something man living in New York, eludes intimacy with women but feeds his deepest desires with a compulsive addiction to sex. When his younger sister temporarily moves into his apartment, stirring up…
8
Porno (2019)
★ 6/10
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
9
Your Friends & Neighbors (1998)
★ 5.8/10
Restless and unhappy, two couples get caught up in infidelity and deception. Barry is a sullen businessman married to Mary, a writer who is unsatisfied with their relationship. Mary begins an affair with Jerry, a smug…
10
Untamed Heart (1993)
★ 6.9/10
Caroline, a young waitress who seems to have bad taste in men, is on her way home one night when thugs attempt to rape her. Adam, the mysterious busboy who works at the same diner, helps fight off the assailants, and…
11
The Longest Ride (2015)
★ 7.6/10
The lives of a young couple intertwine with a much older man as he reflects back on a lost love while he's trapped in an automobile crash.
12
The Package (2018)
★ 5.9/10
When a group of teenagers goes on a spring break camping trip, an unfortunate accident sets off a race to save their friend’s most prized possession.
13
Waking Life (2001)
★ 7.5/10
Waking Life is about a young man in a persistent lucid dream-like state. The film follows its protagonist as he initially observes and later participates in philosophical discussions that weave together issues like…
14
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.
15
The Art of Getting By (2011)
★ 6.6/10
George, a lonely and fatalistic teen who's made it all the way to his senior year without ever having done a real day of work, is befriended by Sally, a popular but complicated girl who recognizes in him a kindred…
16
Fear Below (2025)
★ 6.1/10
A rag-tag team of divers attempting to salvage a sunken car from a river are thwarted by a highly aggressive bull shark.
17
Not Easily Broken (2009)
★ 6.3/10
A car accident and shifting affections test the bond between a married couple.
18
Clown in a Cornfield (2025)
★ 6.1/10
Quinn and her father have just moved to the quiet town of Kettle Springs hoping for a fresh start. Instead, she discovers a fractured community that has fallen on hard times after the treasured Baypen Corn Syrup…
19
Embattled (2020)
★ 6.7/10
The eldest son of a ruthlessly tough MMA champion must fight his way out of the abusive cycle his father has continued.
20
Pimp (2018)
★ 6.2/10
An urban love story set on the hard streets of the Bronx. A struggling female pimp, named Wednesday, grows up learning the game from her dad. Once he's gone she's left to look out for her prostitute mother and…