Movies Like Principal Takes a Holiday

If you liked Principal Takes a Holiday (1998), a family and comedy movie directed by Robert King, 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
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy and tv movie
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
3
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy and tv movie
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
4
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.
5
Who Killed Santa? A Murderville Murder Mystery (2022)
★ 6/10Also comedy and tv movie
A holiday-hating detective is forced to solve a murder — and save Christmas — with help from famous trainees who must improv their way through the case.
6
Robot Chicken: Star Wars Episode III (2010)
★ 7.5/10Also comedy and tv movie
Millions of years from now, after Socrates, Shakespeare and the bible are long forgotten, only two great works will remain: the sci-fi cinema epic Star Wars and Adult Swim's stop-motion animated, cheap gag…
7
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy and tv movie
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.
8
Dave Chappelle: The Closer (2021)
★ 7.2/10Also comedy and tv movie
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.
9
My Spy The Eternal City (2024)
★ 6.5/10Also comedy and family
JJ, a veteran CIA agent, reunites with his protégé Sophie, in order to prevent a catastrophic nuclear plot targeting the Vatican.
10
Dave Chappelle: Sticks & Stones (2019)
★ 7.5/10Also comedy and tv movie
Dave Chappelle takes on gun culture, the opioid crisis and the tidal wave of celebrity scandals in this defiant stand-up special.
11
South Park (Not Suitable for Children) (2023)
★ 7.4/10Also comedy and tv movie
After it's discovered that a teacher at South Park Elementary has an OnlyFans page, Randy is compelled to take a closer look at the seedy underbelly of the world of online influencers.
12
South Park: The End of Obesity (2024)
★ 7.4/10Also comedy and tv movie
The advent of new weight loss drugs has a huge impact on everyone in South Park. When Cartman is denied access to the life-changing medicine, the kids jump into action.
13
South Park the Streaming Wars (2022)
★ 7.1/10Also comedy and tv movie
Cartman locks horns with his mom in a battle of wills while an epic conflict unfolds that threatens South Park’s very existence.
14
The Trailer Park Boys Xmas Special (2004)
★ 6.9/10Also comedy and tv movie
In this holiday prequel, it’s 1997 and Sunnyvale Trailer Park is getting ready for the holiday season. Julian’s got a great idea to make money this Christmas, Ricky gets confused between God and Santa, and Bubbles…
15
Dave Chappelle: Killin' Them Softly (2000)
★ 8.1/10Also comedy and tv movie
Dave Chappelle returns for a stand-up to D.C. and riffs on politics, police, race relations, drugs, Sesame Street and more.
16
Demetri Martin: The Overthinker (2018)
★ 6.8/10Also comedy and tv movie
With his signature one-liners and drawings, Demetri Martin muses on doughnut holes, dogs, sports bars, the alphabet's most aggressive letters and more.
17
Oh, Hello on Broadway (2017)
★ 6.9/10Also comedy and tv movie
Two delusional geriatrics reveal curious pasts, share a love of tuna and welcome a surprise guest in this filming of the popular Broadway comedy show.
18
Demetri Martin: Live (At the Time) (2015)
★ 6.9/10Also comedy and tv movie
Demetri Martin brings his off-kilter take on acoustic guitar, hairless cats, color schemes, and the word "nope" to Washington in his original special.
19
My Science Project (1985)
★ 6.2/10Also comedy and family
His high school teacher issues an ultimatum: turn in a science project or flunk. So Mike Harlan scavenges a military base's junk pile for a suitable gizmo. He finds one... and unwittingly unleashes the awesome power…
20
Tour de Pharmacy (2017)
★ 6.7/10Also comedy and tv movie
A mockumentary that chronicles the prevalence of doping in the world of professional cycling.