Movies like Winning the Bet (2008)
The best movies like Winning the Bet (2008) are Preaching to the Perverted (1997), Pillion (2025) and Fifty Shades of Grey (2015). If Winning the Bet hooked you, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedSecretary (2002)6.8/10 from 2,056 votes
- NewestPillion (2025)Released 2025
Preaching to the Perverted (1997)
A computer wizard infiltrates a London sex club to get evidence for a shutdown, but falls for the proprietress.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisPillion (2025)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisFifty Shades of Grey (2015)
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 as he is rich and powerful, finds himself strangely drawn to Ana, and she to him. Though sexually inexperienced, Ana plunges headlong into an affair -- and learns that Christian's true sexual proclivities push the boundaries of pain and pleasure.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisMy Awkward Sexual Adventure (2012)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisKing Cobra (2016)
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 porn mogul who runs the skin flick empire Cobra Video from his seemingly ordinary suburban home.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisNymphomaniac: Vol. II (2013)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisPink Flamingos (1972)
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 Filthiest Person Alive".
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSecretary (2002)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisTongues Untied (1990)
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 telling the story of his growing up, scenes of men in social intercourse and dance, and various comic riffs, including a visit to the "Institute of Snap!thology," where men take lessons in how to snap their fingers: the sling snap, the point snap, the diva snap.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDifferent for Girls (1997)
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 Karl.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisMandingo (1975)
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 returns from the honeymoon. He also buys his father a new Mandingo slave named Mede to breed and train as a prize-fighter.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisGirlHouse (2014)
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 terrifying fight for her life.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisEating Out 2: Sloppy Seconds (2006)
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 women. He soon finds himself joining the campus ex-gay support group and nabbing a girlfriend! Kyle's ex-boyfriend Marc is horrified at the plan and decides to pursue the confused Troy with his own tactic -- being his "out" gay self. Who will win Troy first?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Duke of Burgundy (2015)
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 conventional, while Evelyn tries to push their taboos even further.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisEmbattled (2020)
The eldest son of a ruthlessly tough MMA champion must fight his way out of the abusive cycle his father has continued.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Bachelor and the Bobby-Soxer (1947)
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 date Susan until the crush abates.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDeath Game (1977)
George Manning is a well-to-do businessman, husband, and father. While his family is away on his birthday, he invites a pair of rain-soaked young women into his house to wait out an evening thunderstorm. The two girls seduce Manning and ultimately kidnap and torture him in his own home.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisThe Little Death (2014)
A comedy film that looks into the loosely connected lives of people with strange sexual fantasies.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Overnight (2015)
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.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisDon Jon (2013)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Belt (1989)
Vittorio, an American novelist teaching in Rome, meets the beautiful but damaged Bianca and they rapidly fall into an urgent, tempestuous affair. He's hesitant over their relationship since she seems to thrive on conflict and is constantly baiting him into physical altercation. Bianca gives Vittorio an exquisite leather belt as a gift; he knows immediately that she wants him to whip her with it. Driven by his craving for her, Vittorio complies to Bianca's desire. Their relationship escalates into a dark realm of S&M which becomes more and more self-destructive.
Why it matches: Similar story and style
The Story of O (1975)
The beautiful O is taken by her boyfriend, Rene, to a bizarre retreat, where she is trained in bondage and sexual perversion...
Why it matches: Similar story and style
SnoozefestMovies like thisTips (2016)
Mario (Thiago Cazado) is in debt. To pay the bills, he displays the body on a famous porn site.
Why it matches: Similar story and style
Title 18 (2022)
An experimental short film made as part of a multi-media triptych, originally screened alongside a fashion collection and an art-installation. Drawing from Papa Yorick’s (Director and fashion designer) thesis “Men Are My Cumrag”, the film reenacts eight mainstay gay porn scripts, incorporating and parodying tropes and clichés, that explore masculine identities within the gay porn industry, through a satirical and critical lens.
Why it matches: Similar story and style
Knife+Heart (2018)
In the summer of 1979, gay porn producer Anne sets out to film her most ambitious film yet, but her actors are picked off, one by one, by a mysterious killer.
Why it matches: Similar story and style
SnoozefestMovies like thisThe Feeling That the Time for Doing Something Has Passed (2024)
A mosaic-style comedy following the life of a woman as time passes in her long-term casual BDSM relationship, low-level corporate job, and quarrelsome Jewish family.
Why it matches: Similar story and style
The Abnormal Female (1969)
A psychiatrist encourages his female patients to tell him their sexual problems, each as each relates her particular case, we see it in flashback.
Why it matches: Similar story and style
S&M Judge (2009)
In 1997, the Belgian public was in shock when judge Koen A. was convicted for the S&M relationship with his wife. Although their life was destroyed by the verdict, Koen and his wife Magda remain together today. The film is a story about dark sexuality and true love, told from the lover's unique point of view
Why it matches: Similar story and style
Popcorn FlickMovies like thisSex, Death & Eyeliner (1999)
Documentary directed by W.K. Border, that which dives into the aspects of contemporary Gothic subculture, vampirism, and BDSM culture. Filmed in 1997 in California.
Why it matches: Similar story and style
Rope Violation (1980)
Satoko, a mentally frail girl, is taken in by Anzai, the owner of a hot springs inn, after her parents commit suicide. One day, the clerk Matsuo forcibly takes Satoko's virginity. The following night, the clerk appears in Satoko's room again. The servant Shozo feels sorry for Satoko and invites her to run away to Tokyo with him. Meanwhile, Shozo steals money from the inn and accidentally kills Matsuo. He buries the body and runs away to Tokyo. Satoko is left alone and is subjected to Anzai's bizarre torture...
Why it matches: Similar story and style
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Frequently asked questions
What are the best movies like Winning the Bet?
The closest matches to Winning the Bet are Preaching to the Perverted (1997), Pillion (2025) and Fifty Shades of Grey (2015). Below are 27 more, each with the reason it matches.
What should I watch after Winning the Bet?
Start with Preaching to the Perverted (1997), the closest match to Winning the Bet.
What is the highest-rated movie like Winning the Bet?
Secretary (2002), rated 6.8/10 by 2,056 TMDB users.
What is the newest movie like Winning the Bet?
Pillion (2025) is the most recent release on this list.
Are there English movies like Winning the Bet?
Yes: Preaching to the Perverted (1997), Pillion (2025) and Fifty Shades of Grey (2015).
How are movies similar to Winning the Bet chosen?
First come films that Trakt’s viewers watch alongside Winning the Bet, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.