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Amy Heckerling’s genius in Clueless broke the implicit link between scruffiness and moral integrity.

It's strange to think of the nineties as another era, if only because I grew up in the nineties but don't yet feel old. But watching 1999's Cruel Intentions, part of TIFF's current Back to the '90s retrospective, there it is: another era. The film opens with the revelation that Ryan Phillippe's character has posted naked photographs of a "conquest" on the Internet – an action meant to characterize him and played for comic effect, that might, by current standards, count as child pornography (and at least as horrific behaviour). Then again, as he later puts it, "E-mail is for geeks and pedophiles."

The retrospective doubles as a postmortem for an era that feels deceptively close. The teenage protagonists of 1990's Pump Up the Volume dress just like twentysomethings do today, and yet, in less perceptible ways, the world is as different now as 1974 was from 1950. Even the teen coming-of-age film feels like an old genre – "I don't know if there ever was an heir apparent to the Amy Heckerlings and John Hugheses of the world," said Jesse Wente, director of film programs at TIFF Bell Lightbox in Toronto. The nineties was the era of the high-school epic – several of the films showing at TIFF are adapted from classic literature – but the idea that senior year is the cradle of the rest of your life seems silly. You have your whole 20s to wonder who you are, while scrambling to build a career and worrying about the end of the world.

Revisiting these movies, the most apparent change seems to be the decline of a certain naive idealism, and the demotion of the naive idealist, who starts the decade as a hero and winds up a joke. By the end of the nineties, Generation X had grown up and shaken its angst, – always less outwardly political than that of the Boomers – and the underdog had become the overdog. "William went to Harvard, where he became one of the most popular students," reads the text below the frowning geek at the end of 1998's Can't Hardly Wait. "He also formed a software company that is now valued at $40-million. He is currently dating a supermodel."

Allan Moyle's Pump Up the Volume is the earliest film in the series, the one that made an icon of Christian Slater as a rebel pin-up. He plays Mark Hunter, a shy teenager who runs a pirate radio station out of his parents' house. At school he's invisible; at night, he exhorts his classmates, fellow members of "the why-bother generation," to rise up against their parents and teachers. "I hate the sixties," he rages, but he still sees the world in terms set out by the Boomers: the little guy, creative and pure of heart, against the unspecified institution.

The anger comes from a sense of restlessness and displacement that most viewers, whatever the times, could probably relate to. Still, the film feels remarkably dated. It's obvious now how banal Mark's ideals are, how selfishly rooted. "I just arrived at this stupid suburb. I have no friends, no money, no car, no licence … there's nothing to do any more. Everything decent's been done, all the great themes have been used up, turned into theme parks." His generational exceptionalism is ridiculous in hindsight; for Mark, the looming nineties are "a totally exhausted decade when there's nothing to look forward to and no one to look up to." Of course, he can look forward to growing up, having kids of his own, dressing them in Descendents T-shirts and hating their favourite bands.

By 1994, the year Reality Bites was released, the idealist antihero has dropped out of college, and besides playing in a band, he does little more than "eat, and couch, and fondle the remote control," as Winona Ryder's protagonist – an overachiever on the ascent – puts it. "I am not under any orders to make the world a better place," he retorts. In Moyle's Empire Records, released the following year, the idealist is shown as a lovable but ineffectual flake, incapable of handling a record-store till, much less the airwaves. (I hated Empire Records when I first saw it, but now it feels charming and wistful, an artifact of an era when the peaceable slacker still had a safe haven in retail.)

Clueless – which leads off the TIFF series, and is arguably the best of the bunch – inverted an entire value system. To someone like Mark Hunter, an unabashed overdog like Cher Horowitz (Alicia Silverstone) – beautiful, rich and popular – could never have played the hero. Amy Heckerling's genius broke the implicit link between scruffiness and moral integrity.

Cher sees right through her idealist love interest, Josh (Paul Rudd) – she knows how ridiculous he is, and pays little mind to how ridiculous he finds her. "We might get Marky Mark to plant a celebrity tree," he says, beaming, as she drives him to a TreePeople meeting. "How fabulous," she replies. "Getting Marky Mark to take time from his busy pants-dropping schedule to plant trees. Josh, why don't you just hire a gardener?" Cher is the status quo; she's also funny, smart and good at heart, and her example shows that rejecting "society" is not only a vague, fruitless endeavour – as part of her audience had certainly figured out – but no fun.

In 1999's 10 Things I Hate About You, the idealist is roasted, not valorized. ("I know how difficult it must be for you to overcome all those years of upper-middle-class suburban oppression," a teacher tells Kat Stratford, the nagging feminist at the film's centre. "… But the next time you storm the PTA, crusading for better lunch meat, or whatever it is you white girls complain about, ask them why they can't buy a book written by a black man.") In Cruel Intentions, a movie about rich kids gleefully putting each other through hell, she doesn't exist. By then, Sex and the City had started its run, and "yuppie greed [was] back," as a character in 10 Things put it. As a kid, my favourite movie was Reality Bites; by the time I got to university in the mid-2000s, I was obsessing over my job prospects and terrified of working in a record store forever.

I asked Jesse Wente what a similar retrospective for the aughts would include; it was surprisingly hard to form a list of contenders. There's a dystopian strain in teen movies now; in the real world, yuppie greed has taken us to a very bad place. Wente wondered if Boyhood was worth considering – not a teen movie by genre, but one of the more notable films to make use of a traditional high-school setting. Boyhood' s protagonist is wiser than Mark Hunter, less entitled than Cher Horowitz, and not at all deluded about the world he's inheriting. Still, he's not quite hopeless – not an idealist, but a warm realist. "The moment seizes us," muses a new college friend, in the film's finale. "It's always right now," he agrees.

Back to the '90s runs at Toronto's TIFF Bell Lightbox to Dec. 26.