Movies Like Playing The Odds

If you liked Playing The Odds (1998), a movie directed by Karen Dior, 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
Preaching to the Perverted (1997)
★ 6.1/10
A computer wizard infiltrates a London sex club to get evidence for a shutdown, but falls for the proprietress.
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
The Little Death (2014)
★ 6.7/10
A comedy film that looks into the loosely connected lives of people with strange sexual fantasies.
4
The Long Weekend (2005)
★ 5.8/10
Cooper is an actor who sees life as one big party, while Ed is in advertising and takes life too seriously. When Ed gets stressed over a deadline he has to meet, his brother Cooper works hard in trying to get his…
5
Different for Girls (1997)
★ 7.1/10
Paul and Kim meet when their vehicles collide. Paul is fascinated with the attractive Kim. It turns out that the two were childhood friends in Catholic boys' school, but back then, before the operation, Kim was named…
6
Zerophilia (2005)
★ 5.9/10
Luke, a young man insecure about his masculinity, discovers he's a Zerophiliac, with the ability to change sex at will. Join Luke as he journeys into the extraordinary world of Zerophilia where so many crazy questions…
7
Sex and Death 101 (2007)
★ 6.2/10
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…
8
X (2011)
★ 6.4/10
A veteran call girl and a runaway prostitute witness a murder which sends them on an out-of-control roller coaster ride through the twilight zone of sex-for-sale.
9
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…
10
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.
11
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…
12
Fedora (1978)
★ 6.7/10
Down-on-his-luck Hollywood producer Barry 'Dutch' Detweiler attempts to lure Fedora, a famous but reclusive film actress, out of retirement, only to discover the horrifying truth behind her success.
13
Mickey's House of Villains (2002)
★ 7.3/10
The villains from the popular animated Disney films are gathered at the House of Mouse with plans to take over. Soon, the villains take over the house and kick out Mickey, Donald and Goofy. It's all up to Mickey and…
14
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…
15
Kid Galahad (1962)
★ 6.2/10
After completing military service, Walter Gulick takes a job as a sparring partner at a gym, the owner of which sees potential in Walter as a professional fighter—and takes him under his wing.
16
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.
17
Zack and Miri Make a Porno (2008)
★ 6.3/10
Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each…
18
The Bachelor and the Bobby-Soxer (1947)
★ 6.9/10
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to…
19
Class (1983)
★ 6/10
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the…
20
Eating Out 2: Sloppy Seconds (2006)
★ 6.1/10
How far would you go to get the person of your dreams? With the help of Gwen and Tiffani, Kyle pretends to be heterosexual in order to land Troy, the new guy (and nude model) who's turning the heads of both men and…