Skip to content

Movies like The Headmistress And. . . The Harlots (2019)

The best movies like The Headmistress And. . . The Harlots (2019) are Loving Annabelle (2007), Mean Girls (2004) and Level 16 (2018). If The Headmistress And. . . The Harlots hooked you, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. 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 this
  2. Mean Girls (2004)

    Cady Heron is a hit with The Plastics, the A-list girl clique at her new school, until she makes the mistake of falling for Aaron Samuels, the ex-boyfriend of alpha Plastic Regina George.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  3. Level 16 (2018)

    The teenage girls of Vestalis Academy are meticulously trained in the art of being “clean girls,” practicing the virtues of perfect femininity. But what exactly are they being trained for? Vivien intends to find out.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  4. The Belles of St Trinian's (1954)

    The unruly schoolgirls of St Trinian's are more interested in men and mischief than homework and hockey. But greater trouble than ever beckons when the arrival at the school of Princess Fatima of Makyad coincides with the return of recently expelled Arabella Fritton, who has the kidnap of a prize racehorse on her mind.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  5. Strike! (1998)

    In 1963 New England, a group of friends at an all-girls academy learn that they're going to be combined with a nearby all-boys institution. They concoct a plan to save their school while dealing with everyday problems along the way.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  6. Barely 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

  7. Wild Child (2008)

    Sixteen-year-old Poppy has everything her unlimited credit cards can buy, and a spoiled attitude to match. After a final thoughtless prank, her exasperated father ships her off to boarding school in England. There, Poppy meets her match in a stern headmistress and a class full of girls who will not tolerate her selfishness.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  8. The Notorious Bettie Page (2006)

    Bettie Page grew up in a conservative religious family in Tennessee and became a photo model sensation in 1950s New York. Bettie's legendary pin-up photos made her the target of a Senate investigation into pornography, and transformed her into an erotic icon who continues to enthrall fans to this day.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  9. The Trouble with Angels (1966)

    Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  10. Scandalous Sex (2004)

    A daughter seeks to restore the reputation of her disgraced father, a wronged college professor. With help of a professional student, she must overcome an ambitious sorority bitch and corrupt college dean.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  11. Welcome to the Club (2022)

    Heart set on becoming a princess, Lisa Simpson is surprised to learn being bad might be more fun.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  12. The School for Good and Evil (2022)

    Best friends Sophie and Agatha navigate an enchanted school for young heroes and villains — and find themselves on opposing sides of the battle between good and evil.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  13. Bottoms (2023)

    Unpopular best friends PJ and Josie start a high school self-defense club to meet girls and lose their virginity. They soon find themselves in over their heads when the most popular students start beating each other up in the name of self-defense.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  14. Matilda (1996)

    Matilda Wormwood is an brilliant and intelligent little girl. Unfortunately, her parents, Harry and Zinnia, fail to see that fact. As time passes, she finally starts school and has a kind teacher, loyal friends, and a terrifying, sadistic headmistress. As she becomes fed up with the constant cruelty, she discovers she has a special gift that she just might be able to use to outwit the unruly adults around her.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  15. Yes, God, Yes (2020)

    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.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  16. Flirting (1991)

    Two freethinking teenagers - a boy and a girl - confront with authoritarian teachers in their boarding schools. The other students treat this differently.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  17. Mischief (1985)

    1956: The shy Jonathan's luck with girls changes when he wins the rebellious Gene as a friend in his last year of high school. Gene is adored by many girls and manages to teach Jonathan a few lessons. Gene himself would rather just be with one girl: his girlfriend Bunny. But since his father is poor, her parents don't accept him.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  18. Police Academy (1984)

    New rules enforced by the Lady Mayoress mean that sex, weight, height and intelligence need no longer be a factor for joining the Police Force. This opens the floodgates for all and sundry to enter the Police Academy, much to the chagrin of the instructors. Not everyone is there through choice, though. Social misfit Mahoney has been forced to sign up as the only alternative to a jail sentence and it doesn't take long before he falls foul of the boorish Lieutenant Harris. But before long, Mahoney realises that he is enjoying being a police cadet and decides he wants to stay... while Harris decides he wants Mahoney out!

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  19. Porno (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 this
  20. These Three (1936)

    Close friends Martha and Karen build a private boarding school together with the aid of the local doctor Joe. The school takes off and many students enroll, one of whom is a trouble-maker who tells a scandalous lie that threatens to destroy the trio's lives.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this

Like The Headmistress And. . . The Harlots and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like The Headmistress And. . . The Harlots?

The closest matches to The Headmistress And. . . The Harlots are Loving Annabelle (2007), Mean Girls (2004) and Level 16 (2018). Below are 17 more, each with the reason it matches.

What should I watch after The Headmistress And. . . The Harlots?

Start with Loving Annabelle (2007), the closest match to The Headmistress And. . . The Harlots.

What is the highest-rated movie like The Headmistress And. . . The Harlots?

Mean Girls (2004), rated 7.2/10 by 9,795 TMDB users.

What is the newest movie like The Headmistress And. . . The Harlots?

Bottoms (2023) is the most recent release on this list.

Are there English movies like The Headmistress And. . . The Harlots?

Yes: Loving Annabelle (2007), Mean Girls (2004) and Level 16 (2018).

How are movies similar to The Headmistress And. . . The Harlots chosen?

First come films that Trakt’s viewers watch alongside The Headmistress And. . . The Harlots, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

↑ ↓ to move · Enter to open · Full search page