The awkwardness of high school is fertile ground for comedy. Hormones/puberty, the first glimpses of freedom, romantic entanglements, and beginning to figure out one’s place in the world, these teenage years are essential if torturous.
In honor of the release of “Booksmart,” below are ten of the best high school comedies to date. Titles that just missed the cut include “10 Things I Hate About You,” “Better Off Dead,” “Charlie Bartlett,” “Clueless,” “Fast Times at Ridgemont High,” “Heathers,” “Just One of the Guys,” “Never Been Kissed,” and “Superbad,” all of which showcase what an embarrassment of riches the subgenre contains.
10“American Pie” (1999)
dir: Paul Weitz
The hilarity of losing one’s virginity is a situation heightened to absurdity with “American Pie,” while also presenting an idealized version of an understanding parent. Without exception, teenagers are often embarrassed by their parents. Jim (Jason Biggs) is embarrassed by his dad (Eugene Levy), but the patriarch’s determination to never judge his son is not just a riot, but consistently touching. Sex isn’t the only part of the high school experience, but it’s the one with the most potential for comedy. Whether it’s the infamous pie scene or Jim’s dad bringing him pornography, awkwardness and discomfort is used here to tremendously funny effect.
9“The Breakfast Club” (1985)
dir: John Hughes
One of the penultimate teen films of the 1980s, “The Breakfast Club” sees teenagers as they are, as opposed to how they’re perceived. John Hughes loved to explore how teenagers of different backgrounds and high school cliques actually had more in common than initially expected. “The Breakfast Club” is an iconic look at just that, with laughter and perceptive observations to spare. Hughes dug below the surface, finding gold in the process.
8“Easy A” (2010)
dir: Will Gluck
Guys who brag in school about sexual exploits, real or perceived, are largely celebrated, but the same does not hold true for women. When rumors suggest Olive’s (Emma Stone) sexual exploits, the gossip is immediately cemented as fact. In a modern day interpretation of “The Scarlet Letter,” Olive opts to hijack the rumor and use it for her social benefit. Satirical and smart, this is much more than just a perfect, star making vehicle for Stone. The commentary here on this gender bias is biting while supremely enjoyable. Witty in its anger, the film takes Nathaniel Hawthorne‘s seminal work and repurposes it as a memorable teen coming-of-age tale.
7“21 Jump Street” (2012)
dir: Phil Lord, Chris Miller
Who would give high school another chance? That juicy concept turned what could have been a shameless money grab instead into an iconic satire with a lot to say. Subverting teen movie tropes, filtered through an action lens, “21 Jump Street” is an unlikely success story. Coming from the mind of Jonah Hill, who nearly cracked this list with “Superbad” as well, the film delights in what a second bite at the apple can be like. The laughs hit quickly, especially when the disparity between modern students behavior and what was acceptable a generation ago are given the spotlight.
dir: Olivia Wilde
Yes, believe the hype. Olivia Wilde‘s directorial debut is without a doubt one of the genre’s best. An instant classic, “Booksmart” is a love letter to the complexities of high school students. Every character here has more to offer than it seems on the surface, from the leads Amy (Kaitlyn Dever) and Molly (Beanie Feldstein), all the way to presumed one note supporting players. There’s plenty of raunchy humor in this film with heart, intelligence, and wit; Wilde has crafted a modern gem. Progressive in its politics, “Booksmart” captures graduation anxiety in an unexpectedly profound manner. The years will only be even kinder to this selection. An update of this list would only push it further towards the top.
5“Ferris Bueller’s Day Off” (1986)
dir: John Hughes
The aforementioned director Hughes celebrates the fun you can have with your friends, in or (especially) out of school. Toying with the formula he established previously, Hughes’ protagonist Ferris Bueller (Matthew Broderick) is the rare teen who is equally popular within every high school clique. More fantastical than much of this list, it’s also arguably the most fun of the lot. Class can be a drag, so sometimes you just need to take a day off. Ferris’ spontaneous decision not only fuels his soul, it helps recalibrate his best friend in the process. At its core, that’s what “Ferris Bueller’s Day Off” truly is about, friendship.
4“Risky Business” (1983)
dir: Paul Brickman
Most high school students have experienced the simple joy of being home alone with the world as their oyster. Sure, “Risky Business” is mostly known for making Tom Cruise a star, but the film also manages to depict the dark comedy of a good kid being bad. Watching Cruise deal with the fallout of that choice is consistently delightful in its zaniness. Most high school comedies are light or contemplative. Here, a dark tonality is used to great affect, helping to separate it from the pack.
3“Mean Girls” (2004)
dir: Mark Waters
What does it mean to be the Queen Bee? Social status and group dynamics reign supreme in high school, and especially within high school cinema. This list is chock full of those depictions, with none leaning as heavily into the social commentary as “Mean Girls.” Tina Fey‘s screenplay dissects the cliques young women form with cutting precision. A modern classic, the film has managed to ingratiate itself within the culture, speaking to now two generations of students. Similar to honorable mention “Charlie Bartlett,” Fey’s script understands why popularity as a segue to acceptance is important to teenagers, but it’s what you do with that status that truly matters.
dir: Alexander Payne
Backstabbing, competition, sex; high school is often a concentrated version of what’s to come in students’ adult life. For Tracy Flick (Reese Witherspoon), it’s her future in politics. A resolute woman determined to get to the top, she sees her path muddied by emasculated authority figures and popularity seeking buffoons alike. Alexander Payne leans into the black comedy aspects of this movie, making a class President election as cutthroat as any national one. A gem upon release, seen through a modern eye, it’s only more savage in how a woman’s path to success is something that men won’t give a second thought to destroying.
1“Dazed and Confused” (1993)
dir: Richard Linklater
The best depiction of what it’s like to advance in high school, “Dazed and Confused” brings incoming freshman and impending seniors together for one wild day and night. Affectionate yet (ironically) sober about high school life, Richard Linklater speaks to what an entire generation experienced. Quotable, featuring one of the best soundtracks ever, and with an infectious spirit, the film stands tall among high school tales. Whether it’s frightened freshmen, optimistic seniors, or that one guy who wishes he was still a student, everyone here is a recognizable figure. Linklater filtered the entire experience into one 24 hour nostalgia jolt.