20. “The Virgin Suicides” (2000)
Across her career to date, through “Lost In Translation,” “Marie Antoinette” and “The Bling Ring,” Sofia Coppola has shown herself to be one of the great chroniclers of isolation, longing, loneliness and rebellion among teen and twentysomething women. But she’s never done just that better than with her debut, “The Virgin Suicides.” Adapted from Jeffrey Eugenides’ novel, it’s a coming-of-age story about the five Lisbon sisters in Michigan in the 1970s, over-protected by their parents to the point of being stifled, leading to them taking their own lives in a suicide pact. This extraordinarily accomplished debut sees Coppola turn the coming-of-age picture into a sort of dreamlike fable, a woozy, sun-dappled, inscrutable modern classic about the repression of female sexuality and the way we mythologize the past.
19. “Rebel Without A Cause” (1955)
There are undeniably creaky elements to Nicholas Ray‘s anthemic teen drama now, but the sizzlingly iconic turn from James Dean is not one of them. Shockingly modern within the confines of a plot that is very much dated to its mid-’50s mores, Dean is a lightning bolt, animating the film and threatening to burn it to a crisp. Sal Mineo as the doomed Plato and Natalie Wood as the incandescent Judy are great in support, as is Jim Backus as the ultimate in uncomprehending fathers, but the film feels almost symbiotically linked to Dean’s performance, for better and worse. Like its confused, fearful, noble but foolhardy protagonist, the film is full of impotent anger — against parents, society, the world: a near-perfect encapsulation of the heady inarticulacy of teenage angst.
18. “Clueless” (1995)
Bar the very occasional exception, the teen movie had ossified and frozen in the early 90s after the John Hughes wave peaked. But then came “Clueless,” the film that reinvented the teen pic and started a new wave that carried on for nearly a decade. Amy Heckerling’s film, a loose adaptation of Jane Austen’s “Emma,” sees popular Beverly Hills girl Cher (Alicia Silverstone) attempt to matchmake her way through high school, but is unable to see either her own superficiality or selfishness, or the potential love-match right in front of her. Hipper and more stylized than most teen movies prior to the time (there’s as much Whit Stillman to it as John Hughes, popularizing a snappy and distinctive turn of phrase that went on to have a huge effect on the way people actually talked), it’s also still as sweet and funny as ever 20 years on, even if the fashion choices have dated.
17. “Say Anything” (1989)
Show us a straight woman who has not idly dreamt of late-’80s John Cusack standing outside her window with a boombox blaring the sappy strains of Peter Gabriel‘s “In Your Eyes” and we’ll show you someone who has not seen Cameron Crowe‘s “Say Anything.” A formulaic story made deliciously fresh and engaging purely by dint of the fantastic performances and note-perfect script (“I gave her my heart and she gave me a pen”), it follows supposed everyman Lloyd Dobler (Cusack) as he gives everything of himself to his relationship with “brain trapped in the body of a gameshow hostess” Diane Court (Ione Skye). Peppered with terrific supporting turns (from Joan Cusack and Lili Taylor among others) the film is really a testament to John Cusack’s offbeat charisma in his role as possibly the most boyfriendable human of all time.
16. “Gregory’s Girl” (1981)
America essentially invented the teenager, and as such it’s no surprise that it’s the master of the teen movie — the UK, for instance, has a tradition of being a teenager that’s more about awkwardness and sexual confusion than prom kings and queens. But sometimes that awkwardness can be an asset, as with the utterly charming “Gregory’s Girl,” from director Bill Forsyth. It’s the story of gangly Gregory (John Gordon Sinclair), who falls for Dorothy (Dee Hepburn), a girl who’s starting to play in the same soccer team, leading to a series of events that see him become seen as an unlikely player in their small town. It’s a tiny, modest film, but one so warm in spirit, so generous in perspective and sweet of nature that it ends up feeling universal. Just avoid 2000’s terrible sequel “Gregory’s 2 Girls” like the plague.
15. “Ferris Bueller’s Day Off” (1986)
Many of the best teen movies are the ones that deal with the outsiders, the freaks, the underdogs. That’s where most of the drama is. So it’s testament to the genius of “Ferris Bueller’s Day Off” that despite focusing on the most popular kid in school — kind of a spoiled asshole of a popular kid at that — it’s still one of the most beloved teen movies of all time. John Hughes’ follow-up to “The Breakfast Club” is a piece of pure wish fulfilment — Ferris (Matthew Broderick) takes the day off, has a blast, learns nothing and suffers no consequences. But it has an anarchic energy that’s all of its own, and Broderick’s indelible performance, and the iconic set pieces that Hughes assembles, turn it into one of film’s greatest celebrations of being young, being irresponsible and living life for the moment.
14. “Cruel Story Of Youth” (1960)
Nagisa Oshima‘s bitterly nihilist, excoriating classic goes by many names, but “Cruel Story of Youth” is probably the most descriptive, barring the working title of “Man, Is This One Hella Grim World.” Oshima, the uncompromising Japanese director behind “In the Realm of the Senses” and “Merry Christmas Mr Lawrence” is never one to shy away from the masochistic in his work, but ‘Cruel Story’ feels especially extreme, visiting attempted rape, actual rape, poverty-induced criminality and botched abortions on its dissociative, vacantly pretty protagonist Makato (Miyuki Kuwano). She falls in to a kind of outlaw-lovers relationship with petty criminal Kiyoshi (Yûsuke Kawazu) who is both her rescuer and her tormentor, but really the film is about the whole apathetic generation of post-war teenagers, who have no outlet for their aggression except antisocial behavior, deliquency, violence and sex.
13. “Election” (1999)
Everything is political, especially high school, and Alexander Payne’s satire “Election,” still the best thing the director’s ever made, proves that pretty definitively. Based on Tom Perrotta’s novel, it focuses on Nebraska history teacher Jim (Matthew Broderick, in a neatly meta bit of casting: it’s as if Ferris Bueller grew up and was defeated by life) overseeing an election which the terrifyingly ambitious Tracy Flick (Reese Witherspoon) looks to walk, so he encourages dim-witted jock Paul (Chris Klein) to stand against her, with Paul’s sister Tammy (Jessica Campbell) entering the race as well. Payne’s skewering of his characters can work against him when he’s trying for something more heart-warming, but here it’s perfect, with a heightened scabrousness that elevates it beyond a teen movie to something bigger about American society. But the witty script, and a perfect cast, keep it from being less finger-wagging, and more like what Billy Wilder would have done if he’d ever made a teen film.
12. “Kids” (1995)
If his schtick has worn increasingly thin over the years, it’s possibly because Larry Clark said everything he needed to say, and then some, about the unthinking cruelty, casual deviance and delirious, consequence-free abandon of teenage sexuality in his explosive, corrosive 1995 feature debut. Genuinely shocking and provocative, with its Harmony Korine screenplay, its bruised-but-beautiful camerawork and its uncompromisingly raw debut performances from Chloë Sevigny, Leo Fitzpatrick, Justin Pierce, Rosario Dawson, and Jon Abrahams, the film is still a queasy watch, and remains a before-and-after demarcation point for the portrayal of juvenile sexuality on film. The biggest issue with it, in fact, may be that in causing such a deservedly massive splash at the time, it sent Clark further down this particular rabbit hole to necessarily lesser, more grubbily gratuitous effect, ever since.
11. “Girlhood” (2014)
Coming-of-age stories should be played-out a genre, yet Celine Sciamma‘s French-language take on the travails of a young black girl (a luminous Karidja Touré) growing up in the tough suburbs of Paris, negotiating gang politics, criminality and her own burgeoning sexuality, is shot through with a vibrant sense of life. According her young, exclusively black, almost exclusively female cast a degree of agency sadly rare for portrayals of this demographic on film, Sciamma’s movie is a thrilling, often poetic meditation on the quest for self-identity. Its setting transcends all its specifics (language, geography, class, skin color, sex) to become something truly universal and achingly relatable — the end of childhood as it really happens: not gradually, but in fits and starts and occasional delirious sessions with your girlfriends yowling along to Rihanna‘s “Diamonds.”