Movies Like Mr. Headmistress

If you liked Mr. Headmistress (1998), a comedy and tv movie movie directed by James Frawley, 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
Clear History (2013)
★ 6.1/10Also comedy and tv movie
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.
2
Identity Thief (2013)
★ 5.9/10Also comedy
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.
3
Stir Crazy (1980)
★ 6.5/10Also comedy
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…
4
Casper Meets Wendy (1998)
★ 5.9/10Also comedy and tv movie
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…
5
Abducted by My Teacher: The Elizabeth Thomas Story (2023)
★ 6.9/10Also tv movie
The story of Elizabeth Thomas, a 15-year-old high school student who was groomed and abducted by teacher Tad Cummins.
6
The Boss (2016)
★ 5.8/10Also comedy
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.
7
So Undercover (2012)
★ 6.1/10Also comedy
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…
8
Under Wraps (2021)
★ 6.8/10Also comedy and tv movie
Three friends try to save their mummified friend, Harold, from greedy criminals by returning him to his resting place before midnight on Halloween.
9
The New Guy (2002)
★ 6/10Also comedy
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?
10
The School for Good and Evil (2022)
★ 7/10Also comedy
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.
11
Godmothered (2020)
★ 6.7/10Also comedy
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…
12
Psych: The Movie (2017)
★ 7.2/10Also comedy and tv movie
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…
13
Fist Fight (2017)
★ 6/10Also comedy
When one school teacher gets the other fired, he is challenged to an after-school fight.
14
The Wizards Return: Alex vs. Alex (2013)
★ 7.8/10Also comedy and tv movie
While trying to prove to her family she can be mature and responsible, teen wizard Alex Russo conjures up a spell to rid herself of her bad qualities, unintentionally creating a Good and Evil Alex. When Evil Alex gets…
15
Invisible Sister (2015)
★ 6.7/10Also comedy and tv movie
Teenager Cleo's school science project goes quite awry, causing her popular older sister Molly to go invisible.
16
Descendants: Wicked Wonderland (2026)
★ 7.5/10Also tv movie
Now that the Queen of Hearts is nice and Cinderella is safe, things seem perfect for Red and Chloe… But little do they know that changing the past created a new villain — Maddox Hatter. When Maddox captures the Queen…
17
How High 2 (2019)
★ 6.2/10Also comedy and tv movie
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…
18
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy and tv movie
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
19
Fired Up! (2009)
★ 6.1/10Also comedy
Popular high schoolers and best friends Shawn and Nick decide to ditch football camp for cheerleader camp. For the girls and for the glory.
20
Nanny McPhee and the Big Bang (2010)
★ 6.3/10Also comedy
Nanny McPhee appears at the door of a harried young mother who is trying to run the family farm while her husband is away at war. But once she’s arrived, Nanny discovers that the children are fighting a war of their…