If history has taught us anything, it’s that producing a quality teen comedy is a risky endeavour, and getting the correct mix of laughs, heart and genuine emotion without coming across as trite, convoluted or lame is a lesson in cultural chemistry. And it’s easy to see the failures out there, as the cinematic world is littered with subpar teen/romantic comedies that attempted to follow the pattern of success crafted by other, more successful filmmakers, only to fail spectacularly along the way. While we won’t do those films the disservice of drawing attention to their mediocrity, what we will do is highlight the exceptional work of the filmmakers who have given us some of the greatest teen comedies of all time; in fact, we’ve got 10 of ’em lined up for you here, with a little something for everyone (John Hughes is for everyone, right?).
10. Risky Business (1987)
Often, a film will be remembered for a single, iconic scene; in 1987’s Risky Business, you’d know that scene in an instant, since it’s been parodied innumerable times in various places. Involving young Tom Cruise, a pink dress shirt, a lack of pants and one classic Bob Seger song about that old time rock and roll, the scene in question has wormed its way into the annals of cinema history, and it’s dragged this Paul Brickman directed film with it. Following the adventures of a young man named Joel Goodson (Tom Cruise), who attempts to have a little fun while his parents are away, with the help of a prostitute named Lana, Risky Business was released to near universal acclaim with critics praising the film’s deeper themes of consumerism and the loss of innocence. The film that launched Cruise towards leading man territory, Risky Business remains a must-watch teen comedy that dabbles in satire and smart humor as well as riotous teenage rebellion.
9. Superbad (2007)
A project long in the works, Superbad was written by Seth Rogen and Evan Goldberg over a period of years during their teens, eventually working its way into development as a project directed by Greg Mottola and starring Michael Cera and Jonah Hill. Following two teens (Cera and Hill) on a single day as they press forward on a journey to supply a party with alcohol to impress girls (the most basic of teen comedy plots, but one that’s wildly effective here given the chemistry between the leads and the ridiculous shenanigans that occur on their adventure), Superbad was also the feature film debut of the now-popular Emma Stone. Critically acclaimed upon its release, with reviewers suggesting it was the next in a long line of quintessential teen comedies that accurately depict some of the struggles associated with coming of age, Superbad is the most recent film on this list and is undoubtedly one of the most important teen films to come out of its era.
8. Clueless (1995)
A contemporary teen comedy that has the distinction of being loosely based off a Jane Austen novel published in 1815, Clueless stars Alicia Silverstone as Cherilyn “Cher” Horowtiz, a well intentioned but spoiled girl who attempts to meddle in the lives of the individuals around her, occasionally to disastrous results. Also starring Stacey Dash, Brittany Murphy (in a career making role) and Paul Rudd, Clueless was released to strong reviews and a solid box office take, but eventually found an even stronger following on home video, where it developed a cult following as one of the few teen comedies on the 1990s that accurately represented the relationships of the young people of the time. The film that made Alicia Silverstone a movie star (if only for a brief period), Clueless holds up better than most films from the 1990s due to its sharp wit and charming cast.
7. Mean Girls (2004)
Directed by Mark Waters and written (and co-starring) the always hilarious and incredibly talented Tina Fey, Mean Girls starred Lindsay Lohan as Cady Heron, a naive homeschooled girl who receives a rude awakening on the intricacies of being a teenage girl when she finds herself thrust into the confusing and complicated world of high school. Also starring Rachel McAdams, Lacy Chabert and Amanda Seyfried as The Plastics, the group of “mean girls” who recruit Cady to join their group, Mean Girls is a hilarious romp that features Fey’s trademark acerbic wit and social commentary. A critical and commercial success that paved the way for several of the film’s stars to have productive movie careers (Lohan has since flamed out pretty hard, but McAdams, Seyfried and co-star Lizzy Caplan are some of the more in-demand actresses working in Hollywood), Mean Girls has become one of the most popular teen comedies released in years, with many citing it as amongst the strongest comedies of its generation.
6. American Pie (1999)
This one’s a real doozy, and it carries with it a special significance as one of the fundamental teenage experiences for many of the everyday internet users out there, who grew up in the American Pie generation. Featuring a huge ensemble cast including Jason Biggs, Eugene Levy, Chris Klein, Tara Reid, Sean William Scott, Mena Suvari, Eddie Kay Thomas, Shannon Elizabeth, Alyson Hannigan and Thomas Ian Nicholas, American Pie follows the misadventures of a group of high school students as they navigate their interpersonal relationships in the face of the approaching prom. A classic teen comedy that spoke to many members of the generation it was filmed for, American Pie draws its name from the notorious and controversial scene wherein the main character (Biggs) logs some quality time with a warm apple pie. With a dynamite soundtrack a little more heart than it’s given credit for, American Pie was a massive home video success that spawned a series of sequels and direct-to-DVD spinoffs.
5. Ferris Bueller’s Day Off (1985)
It’s tough to talk candidly about a movie not only everyone has seen, but one everyone loves; it’s difficult to suss out folks who don’t adore John Hughes’ 1985 classic, Ferris Bueller’s Day Off. One of the most iconic and influential films of the teen comedy genre, Ferris Bueller’s Day Off stars Mathew Broderick as the titular character, a charming young man who decides his time is better spent experiencing the sights and sounds of Chicago than trapped inside his high school. He drags his best friend Cameron (Alan Ruck) and his girlfriend (Mia Sara) along with him, all while trying to avoid getting caught by his dastardly principle, Ed Rooney (Jeffrey Jones). A film featuring many iconic scenes, from the “Twist and Shout” parade sequence to the unveiling of Cameron’s father’s red Ferrari, Ferris Bueller’s Day Off is a film that needs little introduction; it’s a piece of contemporary history, and shouldn’t be missed by anyone.
4. Rushmore (1998)
A quirky little film that isn’t exactly in keeping with most of the movies on this list, Rushmore is too good of a film not to include, despite the fact that it defies convention when it comes to teen comedies. Directed by famous auteur Wes Anderson before he achieved widespread critical and commercial success, Rushmore is an off-beat comedy that stars Jason Schwartzman as Max Fischer, an ambitious student with numerous extra-curricular interests but little interest in school itself, who falls deeply in love with a teacher at his school, Rosemary Cross (played by Olivia Williams). In the process of courting her, Max accidentally introduces her to his older friend Harold Bloom (Bill Murray in a terrific performance), and becomes jealous when the two adults engage in a relationship. Steeped in Anderson’s trademark visual aesthetic and humor, Rushmore was well received critically, features an incredible soundtrack and is consistently cited amongst the greatest films of its generation. Fun fact, it was co-written by frequent Anderson collaborator Owen Wilson, who does not appear in the film.
3. 10 Things I Hate About You (1999)
We’ve spoken of our appreciation for this fundamental teen comedy before, and our love for it has not diminished since the last time we spoke of (and the last time we watched) this insanely lovable film starring Julia Stiles, Heath Ledger, Joseph Gordon Levitt and Larisa Oleynik. A contemporary re-telling of The Taming of the Shrew which sees several young men (Levitt and Ledger) courting the Stratford girls (Stiles and Oleynik), 10 Things I Hate About You is the quintessential ’90s teen comedy; it has a apropos soundtrack, it has the requisite drama and heartfelt emotions necessary of the genre, and it has a charming ensemble cast that help to render the entire film a resounding success, even when watching almost two decades after its release.
2. Dazed And Confused (1993)
This coming of age film is often cited as the most realistic depiction of high school life ever put to film; named after the Led Zeppelin song of the same name, Dazed and Confused takes place over the course of a single day at a high school in Texas, and stars a laundry list of to-be-famous actors and actresses including Jeremy London, Cole Hauser, Ben Affleck, Mila Jovovich, Parker Posey and Mathew McConaughey. Featuring a rocking soundtrack that includes Foghat, Alice Cooper, Deep Purple, KISS and others, Dazed and Confused is one of the most critically acclaimed films on this list, often lauded for addressing many of the deeper issues that plague teens worldwide, such as trepidations about the future, bullying and fitting in.
1. The Breakfast Club (1985)
When people speak of John Hughes and his contributions to both film and the teen comedy genre, they understand it’s impossible to speak of these things without addressing The Breakfast Club, Hughes’ most important and influential film. The story of five youths stuck in detention on a Saturday as they slowly come to realize they are more than the stereotypes they believe each other to be, The Breakfast Club is in many ways the most fundamental of teen comedies; it occupies a rarified space in contemporary culture, as one of the best films of the 1980s and one of the most heartfelt and affective teen comedies of all time. Can any of us conceive of the genre being the same without that iconic final scene, John Bender with his fist in the air, Simple Minds blasting in the background? We think not.