Movies Like Winning the Bet

If you liked Winning the Bet (2008), a movie directed by Ted McIntyre, 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
Pillion (2025)
★ 6.5/10
Colin, a timid man, meets Ray, a confident biker gang leader, who initiates him into a submissive relationship, challenging Colin’s mundane existence and prompting personal growth through their unconventional dynamic.
2
Nymphomaniac: Vol. II (2013)
★ 6.7/10
The continuation of Joe's sexually dictated life delves into the darker aspects of her adult life and what led to her being in Seligman's care.
3
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…
4
Pink Flamingos (1972)
★ 6.1/10
Notorious Baltimore criminal and underground figure Divine goes up against Connie & Raymond Marble, a sleazy married couple who make a passionate attempt to humiliate her and seize her tabloid-given title as "The…
5
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.
6
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.
7
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…
8
Secretary (2002)
★ 6.8/10
A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one.
9
Tongues Untied (1990)
★ 6.7/10
Marlon Riggs, with assistance from other gay Black men, especially poet Essex Hemphill, celebrates Black men loving Black men as a revolutionary act. The film intercuts footage of Hemphill reciting his poetry, Riggs…
10
GirlHouse (2014)
★ 6/10
In an attempt to make some extra cash while away at College, Kylie moves into a house that streams content to an X-rated website. After a deranged fan hacks in to determine the house's location, she finds herself in a…
11
Mandingo (1975)
★ 6.6/10
Warren Maxwell, the owner of a run-down plantation, pressures his son, Hammond, to marry and produce an heir to inherit the plantation. Hammond settles on his own cousin, Blanche, but purchases a sex slave when he…
12
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…
13
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.
14
Fifty Shades Freed (2018)
★ 6.7/10
Believing they have left behind shadowy figures from their past, newlyweds Christian and Ana fully embrace an inextricable connection and shared life of luxury. But just as she steps into her role as Mrs. Grey and he…
15
Over the Top (1987)
★ 6.5/10
Lincoln Hawk a hard-luck big-rig trucker takes us under the glaring Las Vegas lights for all the boisterous action of the World Armwrestling Championship. Relying on wits and willpower, Hawk tries to rebuild his life…
16
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.
17
Fifty Shades Darker (2017)
★ 6.5/10
When a wounded Christian Grey tries to entice a cautious Ana Steele back into his life, she demands a new arrangement before she will give him another chance. As the two begin to build trust and find stability, shadowy…
18
Professor Marston and the Wonder Women (2017)
★ 7.2/10
The unconventional life of Dr. William Marston, the Harvard psychologist and inventor who helped invent the modern lie detector test and co-created Wonder Woman in 1941.
19
The Little Death (2014)
★ 6.7/10
A comedy film that looks into the loosely connected lives of people with strange sexual fantasies.
20
The Overnight (2015)
★ 5.9/10
Alex, Emily, and their son, RJ, are new to Los Angeles. A chance meeting at the park introduces them to the mysterious Kurt, Charlotte, and Max. A family “playdate” becomes increasingly interesting as the night goes on.