Movies Like Richard Herring: The Headmaster's Son

If you liked Richard Herring: The Headmaster's Son (2010), a comedy movie directed by Craig Griffith, 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
Fist Fight (2017)
★ 6/10Also comedy
When one school teacher gets the other fired, he is challenged to an after-school fight.
2
Three O'Clock High (1987)
★ 6.8/10Also comedy
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…
3
29th Street (1991)
★ 6.9/10Also comedy
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.
4
Pretty Persuasion (2005)
★ 5.8/10Also comedy
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
5
The F**k-It List (2020)
★ 6/10Also comedy
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.
6
Accident Man (2018)
★ 6.3/10Also comedy
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.
7
House Party (1990)
★ 6.4/10Also comedy
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…
8
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
9
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
10
#realityhigh (2017)
★ 6.2/10Also comedy
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.
11
Katherine Ryan: Glitter Room (2019)
★ 6.7/10Also comedy
Fresh from a tour, comedian Katherine Ryan shares shrewd observations about school bullies, revenge bodies and raising a very fancy child.
12
Old Dads (2023)
★ 6.2/10Also comedy
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.
13
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
14
Bad Apples (2026)
★ 6.9/10Also comedy
A struggling primary school teacher is forced to take drastic action because of a foul-mouthed, violent student, and uncovers how her community will turn a blind eye to the most outrageous events to preserve harmony…
15
One Night at McCool's (2001)
★ 5.9/10Also comedy
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…
16
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
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.
17
Heathers (1989)
★ 7.2/10Also comedy
A girl who halfheartedly tries to be part of the "in crowd" of her school meets a rebel who teaches her a more devious way to play social politics: by killing the popular kids.
18
I Love My Dad (2022)
★ 5.9/10Also comedy
A hopelessly estranged father catfishes his son in an attempt to reconnect.
19
Demetri Martin: The Overthinker (2018)
★ 6.8/10Also comedy
With his signature one-liners and drawings, Demetri Martin muses on doughnut holes, dogs, sports bars, the alphabet's most aggressive letters and more.
20
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…