Movies like Mr. Headmistress (1998)
The best movies like Mr. Headmistress (1998) are Clear History (2013), Under Wraps (2021) and Casper Meets Wendy (1998). If Mr. Headmistress hooked you with its comedy and tv movie, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLouis C.K.: Hilarious (2010)7.8/10 from 321 votes
- NewestRicky Gervais: Mortality (2025)Released 2025
Clear History (2013)
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisUnder Wraps (2021)
Three friends try to save their mummified friend, Harold, from greedy criminals by returning him to his resting place before midnight on Halloween.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCasper Meets Wendy (1998)
When a warlock threatens Wendy the Good Little Witch, she and her aunts hide out at a resort where Casper the Ghost is vacationing with his uncles. Although Casper and Wendy are told ghosts and witches don't get along, the two are kindred spirits! This spooky family-friendly adventure finds Casper and Wendy bridging the ghost-witch divide to battle the warlock who is intent on destroying Wendy.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisPsych: The Movie (2017)
The ambitious friends come together during the holidays after a mystery assailant targets one of their own. A comedic thrill-ride follows, as the wild and unpredictable Psych team pursues the bad guys, justice … and, of course, food!
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRocko's Modern Life: Static Cling (2019)
After 20 years in space, Rocko returns to a technologically advanced O-Town and makes it his mission to get his favorite show back on the air.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHow High 2 (2019)
When two jobless friends discover a hidden weed bible and the ultimate bud, they think that they’ve got it made…with 'seed' money to start a new snack delivery app. But, when nearly all of their stash and weed bible are stolen, the two potpreneurs set off on an outrageous, mind-bending adventure through Atlanta to find them. Stoned with supernatural powers, they search 'high' and low, stopping at nothing to recover their ticket to starting a legit business.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis C.K.: Hilarious (2010)
In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDave Chappelle: Killin' Them Softly (2000)
Dave Chappelle returns for a stand-up to D.C. and riffs on politics, police, race relations, drugs, Sesame Street and more.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisRicky Gervais: Mortality (2025)
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisIdentity Thief (2013)
When a mild-mannered businessman learns his identity has been stolen, he hits the road in an attempt to foil the thief -- a trip that puts him in the path of a deceptively harmless-looking woman.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisStir Crazy (1980)
New Yorkers Skip Donahue and Harry Monroe have no jobs and no prospects, so they decide to flee the city and find work elsewhere, landing jobs wearing woodpecker costumes to promote the opening of a bank. When their feathery costumes are stolen and used in a bank robbery, they no longer have to worry about employment — they're sent to prison.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAbducted by My Teacher: The Elizabeth Thomas Story (2023)
The story of Elizabeth Thomas, a 15-year-old high school student who was groomed and abducted by teacher Tad Cummins.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Boss (2016)
A titan of industry is sent to prison after she's caught for insider trading. When she emerges ready to rebrand herself as America's latest sweetheart, not everyone she screwed over is so quick to forgive and forget.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisSo Undercover (2012)
When the FBI hires her to go undercover at a college sorority, Molly Morris must transform herself from a tough, streetwise private investigator to a refined, sophisticated university girl to help protect the daughter of a one-time Mobster. With several suspects on her list, Molly unexpectedly discovers that not everyone is who they appear to be, including herself.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe 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 · both comedy
Worth the HypeMovies like thisThe New Guy (2002)
Nerdy high school senior Dizzy Harrison has finally gotten lucky -- after purposely getting expelled, he takes lessons in 'badass cool' from a convict and enrolls at a new school. But can he keep up the ruse?
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGodmothered (2020)
A young and unskilled fairy godmother that ventures out on her own to prove her worth by tracking down a young girl whose request for help was ignored. What she discovers is that the girl has now become a grown woman in need of something very different than a "prince charming."
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisFist Fight (2017)
When one school teacher gets the other fired, he is challenged to an after-school fight.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe 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 · both comedy
Popcorn FlickMovies like thisBang, Boom, Bang (1999)
Bank robber Kalle Grabowski escapes from prison while his unemployed smalltime crook buddy is sitting around doing nothing after he just lost all their money. A fast paced comedy from German director Peter Thorwarth.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisThe Blues Brothers (1980)
Just released from prison, Jake Blues puts his old band back together with his brother Elwood to save the Catholic home where they were raised.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisA Close Shave (1996)
Wallace's whirlwind romance with the proprietor of the local wool shop puts his head in a spin, and Gromit is framed for sheep-rustling in a fiendish criminal plot.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisFace of Evil (1996)
Using her girl-next-door looks to her advantage, Darcy Palmer is a calculating thief and murderer. After killing a young college student and taking her identity, Darcy enrolls in the victim's New England school in her place. At the university, Darcy gets to know her new roommate, Jeanelle, and her handsome father, Russell Polk, who soon play into her next scheme. When Darcy has to alter her plans, both Russell and Jeanelle become quite expendable.
Why it matches: Similar story and style
Bringing Up Baby (1938)
David Huxley is waiting to get a bone he needs for his museum collection. Through a series of strange circumstances, he meets Susan Vance, and the duo have a series of misadventures which include a leopard called Baby.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisAlles nur Tarnung (1996)
After trying to smuggle a package into prison for his father Willi, Harry and his girlfriend Marlies also end up in jail. While Harry is billeted with Daddy, Marlies is housed just one floor up in the cell of the ageing prostitute Jutta. With Christmas just around the corner, the four of them join forces and plan to break through to their cells to celebrate a lavish party with a can of homemade schnapps.
Why it matches: Similar story and style · both comedy
The Olsen Gang Goes to War (1978)
Some criminal EU ministers plan to turn Denmark into a gigantic fair ground and holiday paradise. Egon gets his hand at some important documents which could both make him rich and take care of Denmark's future.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisBig Stan (2007)
A weak con man panics when he learns he's going to prison for fraud. He hires a mysterious martial arts guru who helps transform him into a martial arts expert who can fight off inmates who want to hurt or love him.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Unspoken Truth (1995)
Despite her parents' misgivings, Brianne marries Clay, and the couple soon have a daughter. It's then that Clay begins to show the first signs that he's unhinged. When he sees Brianne innocently talking to a man, Clay shoots him dead. At first, Brianne believes that her love for her husband can prevail. But when authorities threaten to take away custody of her daughter, she learns a horrible truth about her past.
Why it matches: Similar story and style
Ruby & Quentin (2003)
After hiding his loot and getting thrown in jail, brooding outlaw Ruby befriends Quentin, a dim-witted and garrulous giant. After Quentin botches a solo escape attempt, they make a break together. Unable to shake the clumsy Quentin, Ruby is forced to take him along as he pursues his former partners in crime to avenge the death of the woman he loved and get to the money.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Mr. Headmistress?
The closest matches to Mr. Headmistress are Clear History (2013), Under Wraps (2021) and Casper Meets Wendy (1998). Below are 27 more, each with the reason it matches.
What should I watch after Mr. Headmistress?
Start with Clear History (2013), the closest match to Mr. Headmistress.
What is the highest-rated movie like Mr. Headmistress?
Louis C.K.: Hilarious (2010), rated 7.8/10 by 321 TMDB users.
What is the newest movie like Mr. Headmistress?
Ricky Gervais: Mortality (2025) is the most recent release on this list.
Are there English movies like Mr. Headmistress?
Yes: Clear History (2013), Under Wraps (2021) and Casper Meets Wendy (1998).
How are movies similar to Mr. Headmistress chosen?
First come films that Trakt’s viewers watch alongside Mr. Headmistress, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.