Movies like Headmaster's Lessons (2008)
The best movies like Headmaster's Lessons (2008) are Loving Annabelle (2007), Everything You Always Wanted to Know About Sex *But Were Afraid to Ask (1972) and The Bachelor and the Bobby-Soxer (1947). If Headmaster's Lessons hooked you, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedHandsome Devil (2017)7.0/10 from 719 votes
- NewestTitle 18 (2022)Released 2022
Loving Annabelle (2007)
Annabelle is the wise-beyond-her-years newcomer to an exclusive Catholic girls school. Having been expelled from her first two schools she's bound to stir some trouble. Sparks fly though when sexual chemistry appears between her and the Head of her dorm and English teacher, Simone Bradley. Annabelle pursues her relentlessly and until the end the older woman manages to avoid the law.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisEverything You Always Wanted to Know About Sex *But Were Afraid to Ask (1972)
A collection of seven vignettes, which each address a question concerning human sexuality. From aphrodisiacs to sexual perversion to the mystery of the male orgasm, characters like a court jester, a doctor, a queen and a journalist adventure through lab experiments and game shows, all seeking answers to common questions that many would never ask.
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 thisPorno (2019)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLost and Delirious (2001)
After starting at an upmarket boarding school, a teenage girl forms close friendships with her two older roommates. However, when she discovers that her new friends are lovers she finds herself caught in a complicated situation.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisOld Boys (2018)
In the school-set re-working of Cyrano, an awkward but imaginative pupil helps the handsome but spectacularly dim school-hero pursue the fiery daughter of a visiting French teacher.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisBarely Legal (2003)
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 make money and become more popular at school. Hijinks ensue as they cast and create their movie, but porn industry player Vic Ramalot grows jealous of their burgeoning success and tries to put a stop to the project.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies 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 thisWelcome to Chechnya (2020)
This searing investigative work shadows a group of activists risking unimaginable peril to confront the ongoing anti-LGBTQ program raging in the repressive and closed Russian republic. Unfettered access and a remarkable approach to protecting anonymity exposes this under-reported atrocity–and an extraordinary group of people confronting evil.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies 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 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 thisTea and Sympathy (1956)
A sensitive young man recalls his time in boarding school when the only person who seemed compassionate towards him was his housemaster's wife.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisHandsome Devil (2017)
A music-mad 16-year-old outcast at a rugby-mad boarding school forms an unlikely friendship with his dashing new roommate.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisSplendor (1999)
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?
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 thisThe Krays (1990)
Twins Ronnie and Reggie Kray are raised in east London, under the influence of their hateful but doting mother Violet. As they grow up, Ronnie's violent nature takes over, and Reggie follows his brother's lead. The two become notorious crime lords who rule over the East End club scene. But at the height of their power, the brothers veer into different lives, giving the older crime bosses a chance to reclaim what the Krays took from them.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThree O'Clock High (1987)
Nerdy high schooler Jerry Mitchell is assigned to write an article for the school paper about the infamous new delinquent transfer student, Buddy Revell. When Jerry accidentally invades Buddy's personal space and touches him, Buddy challenges Jerry to an afterschool fight in the parking lot, which Jerry tries to avoid at all costs.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisYour Friends & Neighbors (1998)
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 theater professor and husband of her friend, Terri, who is also a writer. Adding to the adulterous mix are Cary, a callous doctor, and Cheri, an art-gallery assistant.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisThreesome (1994)
At a sizable public college, high-minded student Eddy is forced to room with the slovenly Stuart, but the pair strike up a surprising friendship. When attractive co-ed Alex is assigned to live with the two male students because of her gender-neutral name, a roundabout love triangle ensues. Eddy secretly yearns for Stuart, who wants Alex, but she prefers Eddy. The complex situation leads to sexual experimentation and strained relationships.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisShe's the Man (2006)
Viola Hastings is in a real jam. Complications threaten her scheme to pose as her twin brother, Sebastian, and take his place at a new boarding school. She falls in love with her handsome roommate, Duke, who loves beautiful Olivia, who has fallen for Sebastian! As if that were not enough, Viola's twin returns from London ahead of schedule but has no idea that his sister has already replaced him on campus.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Fluffer (2001)
Self-effacing, boyish Sean moves to LA to pursue a career in movies but finds it tougher than he imagined. He stumbles onto porn star Johnny Rebel - a handsome, muscled dream of men and women alike - who awakens Sean’s deep obsession.
Why it matches: Similar story and style
SnoozefestMovies like thisTitle 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 thisI'm a Porn Star (2013)
I'm a Porn Star follows the lives of guys in the neighborhood who are likely a lot more famous than you - at least on the Internet. There are an estimated 370 million pornographic websites on-line. Porn is now a thirteen BILLION dollar business. So who's doing all this moonlighting? Turns out -- probably some people you know.
Why it matches: Similar story and style
The Ages of Lulu (1990)
Fifteen-year-old Lulu has never known any affection from her family. But when she goes to a rock concert with Pablo, a friend of the family, he introduces Lulu to her first sexual experience. Years later, Pablo and Lulu have married; Pablo has created a sheltered, private world for Lulu, into which nothing intrudes. However, Lulu tires of her cloistered existence, and begins hanging out in shady bars, looking for vicarious thrills and danger.
Why it matches: Similar story and style
Popcorn FlickMovies like thisDamon and Hunter: Doing It Together (2006)
Comstock Films has created a unique film series that explores sexual relationships among couples. Each film focuses on one couple and begins with an intimate interview that sets up the background of the couple's relationship: how they met, the basis of their intimacy, what attracts them sexually to one another, and how they share their innermost desires and fantasies. The camera then turns to an intimate lovemaking session, recording in detail the passion and eroticism that exists between the two. Coverage is explicit, but not provocative; it allows viewers to share in the couple's healthy, passionate, romantic relationship and to experience first hand the erotic intimacy of their lovemaking. Damon and Hunter: Doing it Together features the first gay relationship in the series. Damon and Hunter are two adult film stars on the rise, but are also real-life lovers.
Why it matches: Similar story and style
Bulgarian Lovers (2003)
Graying Spaniard Daniel has a healthy budget for indulging in the finer things in life. Daniel's favorite luxury is playing sponsor to younger men amid the lights and sights of Madrid's gay club scene. After Daniel shares a night with handsome Bulgarian emigre Kyril, he finds himself consumed with an insatiable lust for the charismatic foreigner. But, as their relationship takes shape, Daniel's latest conquest reveals his own manipulative tendencies.
Why it matches: Similar story and style
A Day in the Country (2010)
The doctor makes a house call but three is a crowd after the action is over… A film about existential loneliness.
Why it matches: Similar story and style
Body Without Soul (1996)
A stark documentary about young male prostitutes in Prague, aged 15 to 18, who work the streets, train stations, and clubs. Through candid interviews and behind-the-scenes footage of gay porn shoots, the film explores their lives, struggles, and dreams, touching on themes of exploitation, identity, AIDS, and survival.
Why it matches: Similar story and style
Mondo Homo: A Study of French Gay Porn in the '70s (2014)
Between 1975 and 1983 a new kind of film could be seen in French cinema : home-grown gay pornography. The films were shot in 16mm and most of them were passed and given certificates by the CNC (National Cinema Centre). They were screened in a small number of Parisian cinemas dedicated to gay pornographic films : Le Dragon, La Marotte and Le Hollywood Boulevard as well as several in the provinces. They were essentially the work of three production companies : Les Films de La Troïka (Norbert Terry), AMT Productions (Anne-Marie Tensi) and Les Films du Vertbois (principally Jacques Scandelari). The genre met an untimely end with the advent of video, the last being made in 1983 "Mon ami, mon amour (My friend, my lover)". Since then, gay pornography has not been screened in French cinemas. This film is the result of five years of painstaking research and investigation. It features extensive interviews with the directors and actors illustrated by numerous extracts from their films.
Why it matches: Similar story and style
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Frequently asked questions
What are the best movies like Headmaster's Lessons?
The closest matches to Headmaster's Lessons are Loving Annabelle (2007), Everything You Always Wanted to Know About Sex *But Were Afraid to Ask (1972) and The Bachelor and the Bobby-Soxer (1947). Below are 27 more, each with the reason it matches.
What should I watch after Headmaster's Lessons?
Start with Loving Annabelle (2007), the closest match to Headmaster's Lessons.
What is the highest-rated movie like Headmaster's Lessons?
Handsome Devil (2017), rated 7.0/10 by 719 TMDB users.
What is the newest movie like Headmaster's Lessons?
Title 18 (2022) is the most recent release on this list.
Are there English movies like Headmaster's Lessons?
Yes: Loving Annabelle (2007), Everything You Always Wanted to Know About Sex *But Were Afraid to Ask (1972) and The Bachelor and the Bobby-Soxer (1947).
How are movies similar to Headmaster's Lessons chosen?
First come films that Trakt’s viewers watch alongside Headmaster's Lessons, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.