Movies Like Obsessive Affairs

If you liked Obsessive Affairs (1996), a movie directed by Joseph Haggerty, 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 Mustang (2019)
★ 6.9/10
While participating in a rehabilitation program training wild mustangs, a convict at first struggles to connect with the horses and his fellow inmates, but he learns to confront his violent past as he soothes an…
2
Wasteman (2026)
★ 7.3/10
Taylor's hopes for a fresh start post-parole are jeopardised by cellmate Dee's arrival. As Dee takes Taylor under his wing, a vicious attack tests their bond, forcing Taylor to choose between protecting Dee and his own…
3
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…
4
The Unforgivable (2021)
★ 7.4/10
A woman is released from prison after serving a sentence for a violent crime and re-enters a society that refuses to forgive her past.
5
Jamesy Boy (2014)
★ 6.4/10
Based on the true story of teenager James Burns who goes from a suburban street gang to a maximum-security prison cell surrounded by hardened criminals. He turns his life around in prison thanks to the unexpected…
6
A Bluebird in My Heart (2018)
★ 5.9/10
An ex-con's attempts to live a quiet life are derailed when the daughter of the woman sheltering him is the victim of a vicious attack.
7
The Woodsman (2004)
★ 6.8/10
After twelve years in prison, Walter returns home. His family has abandoned him, save for his brother-in-law. Few know he's a sex offender and pedophile. Walter finds an apartment and is regularly visited by his parole…
8
Dog Pound (2010)
★ 7.2/10
Three juvenile delinquents arrive at a correctional center and are put under the care of an experienced guard.
9
The Trials of Cate McCall (2013)
★ 6.4/10
In order to be reinstated to the bar and recover custody of her daughter, a hotshot lawyer, now in recovery and on probation, must take on the appeal of a woman wrongfully convicted of murder.
10
Strange Weather (2016)
★ 5.9/10
Years after her son's suicide, a woman longs to confront both the past and a friend of his who took his business idea.
11
South of Heaven (2021)
★ 6.4/10
Convicted felon Jimmy gets early parole after serving twelve years for armed robbery. Upon his release, he vows to give Annie, his childhood love, now dying from cancer, the best last year of her life – unfortunately…
12
The Boss (2016)
★ 5.8/10
A titan of industry is sent to prison after she's caught for insider trading. When she emerges ready to rebrand herself as America's latest sweetheart, not everyone she screwed over is so quick to forgive and forget.
13
Beats (2019)
★ 6.7/10
An agoraphobic hip-hop prodigy and a disgraced former music manager cross paths in Chicago’s South Side and help each other face demons of their pasts.
14
Let's Go to Prison (2006)
★ 6/10
When a career criminal's plan for revenge is thwarted by unlikely circumstances, he puts his intended victim's son in his place by putting him in prison...and then joining him.
15
Down by Law (1986)
★ 7.4/10
A disc jockey, a pimp and an Italian tourist escape from jail in New Orleans.
16
Get Rich or Die Tryin' (2005)
★ 6.9/10
A tale of an inner city drug dealer who turns away from crime to pursue his passion, rap music.
17
Mammal (2016)
★ 6.3/10
After Margaret, a divorcée living in Dublin, loses her teenage son, she develops an unorthodox relationship with Joe, a homeless youth. Their tentative trust is threatened by his involvement with a violent gang and the…
18
Monster (2003)
★ 7.2/10
In 1989, prostitute Aileen Wuornos befriends and enters a relationship with a young woman named Selby. Determined to straighten out her life, Aileen's limited education lands her back on the corner. She's raped by a…
19
Return to Sender (2015)
★ 6.1/10
A nurse mistakes a stranger who pays her a visit for her blind date and soon, the man rapes her and turns her life upside down. The woman works to reclaim her life and exact revenge on her assailant after he's paroled…
20
Hustle & Flow (2005)
★ 7.2/10
With help from his friends, a Memphis pimp in a mid-life crisis attempts to become a successful hip-hop emcee.