Movies like Richard Herring: The Headmaster's Son (2010)
The best movies like Richard Herring: The Headmaster's Son (2010) are Fist Fight (2017), Three O'Clock High (1987) and John Mulaney: Kid Gorgeous at Radio City (2018). If Richard Herring: The Headmaster's Son hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedJohn Mulaney: Kid Gorgeous at Radio City (2018)7.9/10 from 259 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Fist 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 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 · both comedy
Popcorn FlickMovies like thisJohn Mulaney: Kid Gorgeous at Radio City (2018)
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisBill Burr: Drop Dead Years (2025)
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe F**k-It List (2020)
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAccident Man (2018)
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisPretty Persuasion (2005)
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisI Love My Dad (2022)
A hopelessly estranged father catfishes his son in an attempt to reconnect.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisHouse Party (1990)
Young Kid has been invited to a party at his friend Play's house. But after a fight at school, Kid's father grounds him. None the less, Kid sneaks out when his father falls asleep. But Kid doesn't know that three of the thugs at school have decided to give him a lesson in behavior.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShane Gillis: Beautiful Dogs (2023)
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like this#realityhigh (2017)
When nerdy high schooler Dani finally attracts the interest of her longtime crush, she lands in the cross hairs of his ex, a social media celebrity.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like this29th Street (1991)
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisOld Dads (2023)
A cranky middle-aged dad and his two best friends find themselves out of step in a changing world of millennial CEOs and powerful preschool principals.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis C.K.: Ridiculous (2026)
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisDave Chappelle: The Closer (2021)
As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisOne Night at McCool's (2001)
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a tussle with her criminal boyfriend, who she then shoots dead, later persuading Randy to take the rap for her. But this isn't the end of it, as both Randy's cousin Carl and the detective assigned to the murder case also fall for Jewel's charms and find themselves caught up in the ensuing events. It seems that any man who meets Jewel falls instantly in love with her, and she's going to use this fully to her own advantage, leaving a trail of havoc in her wake. It also seems that she is going to get away with it - that is, until Randy decides to hire a hitman...
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisAli Wong: Single Lady (2024)
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJackass Presents: Bad Grandpa (2013)
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCa$h (2010)
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a tumultuous adventure through the streets of Chicago, each are pulled deeper and deeper into a desperate spiral of deception and violence – all in the name of money.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisKud Wafter (2021)
The Little Busters’ outing went off peacefully, and now that the summer holidays have started, most baseball team members have gone home. Among the few still around are Riki Naoe and Kudryavka “Kud” Noumi. However, Masato has caused quite a bit of damage to the boys’ dormitory by hitting it awkwardly with a baseball, so it is now underwater. A new place to stay is needed, so the boys are unceremoniously put up with the girls. However, not everyone will be able to enjoy the luxury of a bed.
Why it matches: Similar story and style · both comedy
Superbad (2007)
Two co-dependent high school seniors are forced to deal with separation anxiety after their plan to stage a booze-soaked party goes awry.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisTell 'Em Steve-Dave: Live at the Gramercy Theatre (2017)
Tell 'Em Steve-Dave presents the first live podcast concert movie!
Why it matches: Similar story and style · both comedy
Growth Vitamin (1988)
The teacher at school made a scientific experiment - he put two rats in different cages. One of the rats was given carrots containing vitamin of growth, and the other did not feed. Time passed, and the rat, to whom nothing was given, became thicker than the rat that was fed. It turned out that one student from pity fed another rat.
Why it matches: Similar story and style · both comedy
Bedside Dentist (1971)
Thomas, a naive young dental student, faces a rather difficult challenge. His millionaire aunt, a bit of a sex nut, will give both him and his dental school millions if he can prove that he is sexually able and skillful. His schoolmates hear rumors of this trial, but understand the challenge to be for him to keep his celibacy.
Why it matches: Similar story and style · both comedy
88-öresrevyn (1971)
Dinner revue that features both satire and other sketches and music numbers.
Why it matches: Similar story and style · both comedy
Louis C.K.: Shameless (2007)
Louis C.K. is back on HBO in an ALL-NEW hour of raw no-holds-barred stand-up comedy! The creator and star of the 2006 comedy series Lucky Louie, performs in front of a live audience in LA at the Henry Fonda Theater. Louis C.K. covers issues near and dear to his heart like marriage, lying to your spouse, having kids and losing your privacy, and obligatory sex among husbands and wives.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisLolo (2019)
Lolo is an openly gay 11-year-old boy trying to finally convince Max, his first love, to go public with their relationship at the school party. Max also wants a relationship but Lolo might not be the one. Lolo’s best friends, Elena and Toby, help him to overcome this situation and give him the support that he needs.
Why it matches: Similar story and style · both comedy
Vice Versa (1988)
A mysterious oriental skull transforms a father into his son, and vice versa.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisRobin Williams: Weapons of Self Destruction (2009)
HBO presents one of the most gifted and revered performers of our time, Academy-Award winning Robin Williams, starring in his fifth exclusive HBO special, taped before a live audience at Washington's Constitution Hall.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Richard Herring: The Headmaster's Son?
The closest matches to Richard Herring: The Headmaster's Son are Fist Fight (2017), Three O'Clock High (1987) and John Mulaney: Kid Gorgeous at Radio City (2018). Below are 27 more, each with the reason it matches.
What should I watch after Richard Herring: The Headmaster's Son?
Start with Fist Fight (2017), the closest match to Richard Herring: The Headmaster's Son.
What is the highest-rated movie like Richard Herring: The Headmaster's Son?
John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.
What is the newest movie like Richard Herring: The Headmaster's Son?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like Richard Herring: The Headmaster's Son?
Yes: Fist Fight (2017), Three O'Clock High (1987) and John Mulaney: Kid Gorgeous at Radio City (2018).
How are movies similar to Richard Herring: The Headmaster's Son chosen?
First come films that Trakt’s viewers watch alongside Richard Herring: The Headmaster's Son, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.