Movies Like Terms of Endowment

If you liked Terms of Endowment (2001), a movie directed by Chris Ward and J.D. Slater, 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
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.
3
Babylon (2022)
★ 7.3/10
A tale of outsized ambition and outrageous excess, tracing the rise and fall of multiple characters in an era of unbridled decadence and depravity during Hollywood's transition from silent films to sound films in the…
4
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…
5
Champagne Problems (2025)
★ 6/10
A driven American exec heads to Paris determined to acquire a champagne brand by Christmas — and accidentally falls for the heir to the bubbly empire.
6
King Cobra (2016)
★ 5.8/10
It’s 2006, YouTube is in its infancy, and internet porn is still behind a paywall. Taking the stage name Brent Corrigan, a fresh-faced, wannabe adult video performer is molded into a star by Stephen, a closeted gay…
7
Horrible Bosses 2 (2014)
★ 6.2/10
Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.
8
Pretty Persuasion (2005)
★ 5.8/10
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
9
Deuce Bigalow: Male Gigolo (1999)
★ 6/10
Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking…
10
Batman vs. Two-Face (2017)
★ 6.3/10
Former Gotham City District Attorney Harvey Dent, one side of his face scarred by acid, goes on a crime spree based on the number '2'. All of his actions are decided by the flip of a defaced, two-headed silver dollar.
11
A Bad Moms Christmas (2017)
★ 6.3/10
Amy, Kiki and Carla – three under-appreciated and over-burdened women – rebel against the challenges and expectations of the Super Bowl for mothers: Christmas. And if creating a more perfect holiday for their families…
12
Jungleland (2020)
★ 6.4/10
Stanley manages his boxer brother Lion but when a devastating loss in the ring leaves the pair in debt, an opportunity to recoup the cash leads to a series of misadventures that threaten to break the bond between them.
13
29th Street (1991)
★ 6.9/10
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
14
The Duke of Burgundy (2015)
★ 6.3/10
Day in and day out, lovers Cynthia and Evelyn enact an elaborate sadomasochistic fantasy as mistress and maid. But as their ritual of domination and submission begins to turn stale, Cynthia yearns for something more…
15
Beyond a Reasonable Doubt (1956)
★ 6.8/10
A newspaper publisher, wanting to prove a point about the insufficiency of circumstantial evidence, talks his possible son-in-law Tom into a hoax in an attempt to expose ineptitude of the city's hard-line district…
16
Hands of Stone (2016)
★ 6.6/10
The legendary Roberto Duran and his equally legendary trainer Ray Arcel change each other's lives.
17
Looking for Richard (1996)
★ 6.8/10
Al Pacino's deeply-felt rumination on Shakespeare's significance and relevance to the modern world through interviews and an in-depth analysis of "Richard III."
18
Fifty Shades of Grey (2015)
★ 5.9/10
When college senior Anastasia Steele steps in for her sick roommate to interview prominent businessman Christian Grey for their campus paper, little does she realize the path her life will take. Christian, as enigmatic…
19
Yes, God, Yes (2020)
★ 6.3/10
Alice, a young innocent Catholic girl, is tempted into masturbating after an AOL chat suddenly turns sexual, however is conflicted as the act would be considered a sin.
20
Road Trip (2000)
★ 6.3/10
After a student at the University of Ithaca films his one-night stand with a beautiful sorority girl, he discovers one of his friends has accidentally mailed the homemade sex tape to his girlfriend in Austin. In a…