In the final months of the twentieth century, millions of Americans believed we were headed toward a reckoning—so much so, they spent what was left of the nineties gearing up for a meltdown. Some converted their homes into DIY fallout shelters, stocking them with canned chow mein, toilet paper, or three-hundred-gallon waterbeds (which they could pop open and drink from in the event of a drought). Others prepared by buying guns—lots of guns. Less than two weeks before the arrival of the new millennium, the FBI received 67,000 gun sale background check requests in a single day, setting a new record. Many of those applicants had no doubt become obsessed with the “millennium bug”—a data hiccup that would supposedly cause thousands of computers to simultaneously collapse, unable to recognize the changeover from 12/31/99 to 01/01/00.

The US government, along with several corporations, had spent an estimated $100 billion combined to upgrade their machines in time. In Silicon Valley, Y2K worries were so pitched that Apple head Steve Jobs commissioned a Super Bowl ad featuring HAL, the creepily sentient computer system from Stanley Kubrick’s 1968 sci-fi trip 2001: A Space Odyssey. The commercial finds HAL speaking from the future, where he apologizes for the chaos caused by the changeover. “When the new millennium arrived,” HAL says coldly, “we had no choice but to cause a global economic destruction.” (The only computers to avoid the meltdown, according to HAL, were made by Apple.)

The famously private Kubrick would later call Jobs, telling him how much he had enjoyed the spot. Yet some in the tech industry didn’t find the prospect of Y2K funny. There was a real fear that, no matter what we did to prepare, Prince’s famed pop prophecy was bound to come true: “Two-thousand-zero-zero/party over/oops/out of time.” “I’ve seen how fragile so many software systems are—how one bug can bring them down,” a longtime programmer told Wired. He’d retreated into the California desert and built a solar-powered, fenced-off New Year’s Eve hideaway (he also bought his very first gun, just in case). Others saw Y2K as a potential biblical event: in Jerry Falwell’s home video Y2K: A Christian’s Survival Guide to the Millennium Bug, available for just under $30 a pop, the smug televangelist—last seen warning his flock about the gay agenda of the Teletubbies—cautioned that Y2K could be “God’s instrument to shake this nation, to humble this nation” (he also advised loading up on ammo, just in case).

Whether they were freaked out by technology or theology, many of the end-timers shared a common tut-tutting anxiety: namely, that we’d advanced a bit too much during the twentieth century, sacrificing our humanity in favor of ease and desire. And now retribution was due, whether it took the form of an act of God or a downloadable rapture. As one mother of three sighed in the December 31, 1999, edition of the New York Times, “It just seems like the end is getting closer.”

If the collapse of civilization was upon us, the timing couldn’t have been worse. In 1999, the United States was in the midst of an unexpected comeback. The decade had begun with a recession, pivoted to a foreign war, and nearly culminated in a president’s removal from office. Now, across the country, people were indulging in a wave of contagious optimism. You could see that giddiness on Wall Street, where, throughout 1999, the Dow Jones, the NASDAQ, and the New York Stock Exchange had all experienced hypercharged highs. You could sense it on the radio, where the gloom raiders who’d soundtracked so much of the decade had been replaced by teen cutie pies and loca-living pop stars. You could even experience it via the digital dopamine rush of the internet, which was still in utero—and still populated by weirdos—but which had the potential to make everyone smarter or richer than they’d ever imagined. In just a few years, Jeff Bezos had transformed from an online bookseller to an all-encompassing twenty-four-hour shopping mall (Bezos’s awkwardly smiling face would be stuffed into a cardboard box for Time’s 1999 Person of the Year cover). And before the year was over, the recently launched movies-by-mail company Netflix would raise $30 million in funding, and introduce its first monthly DVD-rental plan.

But the surest way to feel that static-electric zap of possibility was to walk into a movie theater in 1999—the most unruly, influential, and unrepentantly pleasurable film year of all time.

It began with January’s Sundance Film Festival debut of The Blair Witch Project—a jumpy, star-free vomit comet—and ended with the December deluge of Magnolia, the movie-ist movie of the year, featuring a 188-minute running time, a plague of frogs, and the sight of megaceleb Tom Cruise crotch thrusting his way to catharsis. In between came a collision of visions, all of them thrillingly singular: The Matrix. The Sixth Sense. Election. Rushmore. Office Space. The Virgin Suicides. Boys Don’t Cry. Run Lola Run. The Insider. Three Kings. Being John Malkovich. Many of those films—along with Star Wars: Episode 1—The Phantom Menace, the most unpopular popular movie of the year, if not of all time—would break the laws of narrative, form, and even bullet-time–bending physics. In 1999, “The whole concept of ‘making a movie’ got turned on its head,” proclaimed writer Jeff Gordinier in a November cover story in Entertainment Weekly. “The year when all the old, boring rules about cinema started to crumble.”

Yet for all their audacity, the movies of 1999 were also sneakily personal, luring viewers with promises of high-end thrills or movie star grandeur—only to turn the focus back on the audience, forcing them to consider all sorts of questions about identity and destiny: Who am I? Who else could I be? The body-bending thrills of The Matrix; the white-collar uprisings of Fight Club and Office Space; the self-seeking voyages of Being John Malkovich and Boys Don’t Cry; the Xbox-on-ecstasy story line swaps of Go and Run Lola Run. Each was a glimpse of not just an alternate world but an alternate you—maybe even the real you. As exhilarating as it was to walk into a theater that year, it felt ever better to float on out, alive with a sense of potential, the end credits hinting at a new start. Maybe something amazing was awaiting us on the other side of 1999.

“It was a new century—the beginning of a new story,” says director M. Night Shyamalan, whose spiritual shocker The Sixth Sense would become 1999’s second-highest-grossing movie. “And it was a time for original voices. The people paying to make the movies—and the people going to the movies—all said, ‘We don’t need to know where we are going. We trust the filmmaker.’?”

Studio executives have long lusted for the so-called four-quadrant movie—a film that appeals equally to men and women, young and old. But 1999 was a four-quadrant year: it had something for everyone. The domestic box office pulled in nearly $7.5 billion, and although some of that was fueled by franchise entries such as Toy Story 2 and Austin Powers: The Spy Who Shagged Me, many of the most successful films of 1999 were complete originals: The Matrix, The Sixth Sense, American Beauty, American Pie, Notting Hill, and The Blair Witch Project all made more than $100 million, even though none was based on a comic book series, a TV show, or a real-life witch (despite what some Blair viewers may have believed). “One thing I learned from my farmer friends is that, every twenty or thirty years, you get a good harvest,” says actor Luis Guzmán, who appeared in Magnolia and The Limey (and who spends a good amount of time in rural Vermont). “And that’s how I look at the movies from 1999.”

Film dictated the conversation that year—which is impressive when you consider just how satisfyingly overstuffed 1999 was. Top-forty pop had just been reignited by MTV’s Total Request Live and such crazy-sexy-cruel mainstays as Britney Spears, Christina Aguilera, Eminem, and Limp Bizkit’s Fred Durst. And the January arrival of the mob drama The Sopranos—the most must-see TV show in a year that was full of them, from The West Wing to Freaks and Geeks—heralded a small-screen overthrow that would only become more pronounced in the years to come.

But in 1999, the movies were still the higher power of popular culture. You had to see Fight Club—or American Beauty or Rushmore or Magnolia—if for no other reason than to see what everyone else was talking about.

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There’d been other years like this, of course—ones in which film took an almost teleportative leap forward, reinventing and reviving itself in front of our very eyes. In 1939, the triple-headed tornado of The Wizard of Oz, Gone With the Wind, and Stagecoach reimagined what big-screen storytelling could look like. The year 1967 saw the generation-defining (and generation-dividing) debuts of Bonnie and Clyde and The Graduate, while a decade later came Star Wars, Annie Hall, and Eraserhead—a trio of films that are still being ripped off and riffed upon today. Even a relatively shallow season like 1985, which occurred smack in the middle of the escapist Reagan era, could find room for sneak-attack thrills such as Brazil, After Hours, and Desperately Seeking Susan. Pretty much every movie year is a good one, even if you have to do some searching to find the masterworks or minimovements.

But in 1999, sixty years after Dorothy dropped a house into Oz, a group of filmmakers started their own Technicolor riot, one that took place right on the fault line of two centuries, and drew power and inspiration from both. Many of the directors, writers, and executives from that year were de facto film scholars—some educated at NYU or USC, some by VHS—and their movies shared a reverence for what had come before. It wasn’t hard to connect The Matrix’s reality-revealing red pill to Oz’s yellow brick road; or the fax-and-mouse games of The Insider to the hush-hush muckraking of All the President’s Men; or the adrift suburban teens of The Virgin Suicides to the ones in Sixteen Candles.

“We may be through with the past, but the past ain’t through with us,” is the oft spoken mantra of Magnolia, and the past was everywhere you looked in 1999—as if all of those previous cinematic epochs had been compressed, burned onto a zip drive, and passed around from one filmmaker to the next. The movies that loomed largest over 1999 were the ones produced between 1967 and 1979—a period that saw an unparalleled, and today unthinkable, combination of high-IQ thrillers, confrontational comedies, and existentially troubled dramas. For many late-nineties directors, the so-called Easy Riders, Raging Bulls filmmakers—named after Peter Biskind’s myth-making 1998 book—were the big screen’s own greatest generation, executing wild ideas with big-studio backing. “They were movies that dealt with the texture of real life,” says director Alison Maclean, whose 1999 druggie travelogue Jesus’ Son was influenced by such rough-and-tumble seventies pictures as The Long Goodbye and The Panic in Needle Park. “There’s a soulfulness to those films, and a sense of spiritual crisis—of something being broken.”

Decades later, that unvarnished, unfulfilled sense of purpose-driven ennui crept back into movie theaters. Sometimes the links between the movies of 1999 and the films of the Nixon/Carter years were atmospheric: the Gulf War–set Three Kings echoed such combative black comedies as M*A*S*H and Catch-22, while the doomed heartland romance in Boys Don’t Cry recalled the one in Badlands. Other times, the filmmakers had consciously sought to forge connections with the past. Pedro Almodóvar’s Oscar-winning All About My Mother—a vibrant heartbreaker about love and theater—was inspired by John Cassavetes’s 1977 drama Opening Night. Before shooting Magnolia, writer-director Paul Thomas Anderson held cast and crew screenings of the 1976 tragicomedy Network for inspiration. And no movie seduced quite as many filmmakers as 1967’s The Graduate, the quintessential tale of rudderless youth that informed everything from Fight Club to Rushmore to American Pie.

But that reverence toward film’s history was matched by a desire to fuck around with its future. Everything was up for grabs in 1999—visually, narratively, thematically. The old “It’s like movie X meets movie Y” descriptors simply didn’t compute anymore. “I remember looking at that lineup in ’99 and thinking, ‘Name me any year between 1967 and 1975 that had more really original young filmmakers tapping into the zeitgeist,’?” says Fight Club’s Edward Norton. “I would stack that year up against any other.” Adds Sam Mendes, whose suburban nightmare debut, American Beauty, earned Academy Awards for Best Director and Best Picture: “It’s astonishing how many different genres were being redefined. Is The Sixth Sense a horror movie, a thriller, or a ghost story? What is Fight Club? What is Being John Malkovich? Even American Beauty—is it a coming-of-age tale or a fantasy? Something was definitely shifting.”

It wasn’t just genres that were evolving in 1999. Storytelling itself was in the middle of a mutation. Aided by quick-moving digital editing machines and cheap video cameras, filmmakers ripped up and remixed the century-old rules of cinema, screwing with time, perspective, and expectations. Movies such as the madcap Go or Steven Soderbergh’s crisp neo-noir The Limey treated traditional story beats like Tetris blocks, stacking them atop or snugging them around one another—or letting them fall, just to see what form they might take. And The Matrix and The Phantom Menace used immersive digital effects to render entire artificial worlds, which could then be altered with a computer; it was almost as if the filmmakers could actually reach right into the frame and reorder their onscreen universe.

Audience members—who’d spent the nineties retraining their brains to absorb everything from reality TV to Resident Evil to pixel-dusted webcam videos—were willing to play along, even if they didn’t always know what they were getting into. “The entire narrative structure of movies exploded,” notes Lisa Schwarzbaum, an Entertainment Weekly film critic from 1991 to 2013. “You could tell stories in pieces, or backward. You could be lost at the beginning, or you could repeat things, or you could have people flying around the Matrix.”

At times the movies of 1999 felt like part of some mass insurrection, one overseen by three overlapping generations of idiosyncratic filmmakers. “These are very eclectic, interesting directors, who have all stood the test of ‘Do you have anything really to say?’?” notes Fincher, who refers to his peers as “precocious, inspired lunatics.” “Speed was one of the biggest movies that had ever been made at that time—but was [director] Jan de Bont a voice? No. These directors we’re talking about all have something that stains what they do.”

Some of the Class of ’99—including Eyes Wide Shut’s Stanley Kubrick and The Thin Red Line’s Terrence Malick—were returning to moviemaking for the first time in decades. Others, such as Michael Mann (The Insider), had been revered as sly, stylish troublemakers since at least the eighties. Then there were the upstarts who’d begun their careers in the world of lower-budget indies: Wes Anderson (Rushmore), the Wachowskis (The Matrix), and Alexander Payne (Election), among several others. In 1999, they’d all be joined by such nü-brat debutantes as Sofia Coppola, Spike Jonze, and Kimberly Peirce. “We were de facto not the establishment,” Peirce says of her contemporaries. “A bunch of us were reacting to the bigger and more actiony movies of the nineties, saying, ‘That’s not how I think—but I have this story that I really love, one that’s smaller and weirder.’?”

Nearly all the filmmakers of 1999 opted to tell stories that were similarly personal (even if they weren’t always quite so small-scale). And they often subverted the expectations of their own fans. Few would have guessed, for example, that Magnolia’s Paul Thomas Anderson would follow his sweaty porn-biz odyssey Boogie Nights with a sober drama about cancer and interconnectivity. Nor would anyone have predicted that David Lynch—who’d spent the decade making such provocations as Twin Peaks: Fire Walk with Me—would close out the nineties with a film like The Straight Story, a G-rated, Disney-released tale of an elderly man traveling cross-country on a tractor to visit his ailing brother. If the writers and directors of 1999 shared one unspoken trait, it was the ambition to make something no one had seen before. “Young and older generations came together in this exploratory way,” says Run Lola Run writer-director Tom Tykwer. “There was this beautiful competition between experimental filmmaking and the so-called established filmmaking. But they were also giving each other fire and enthusiasm.”

And they were doing so in a year in which some people were penciling the apocalypse on their calendar, just in case. “There was so much going on about Y2K, and so much talk about computers going haywire, that it even reached down to the people who thought it was total malarkey,” says The Straight Story cowriter and editor Mary Sweeney. “It was the end of a very dramatic decade.”

While the nineties would later be revised by some as a sort of pre-9/11 paradise, the period had in fact been marked by social and political tumult: the beating of Rodney King, the battle over Anita Hill, and terrorist attacks like the bombing in Oklahoma City. By the time 1999 arrived, it felt like anything could happen. “People forget how much anxiety there was,” says Norton. “It was the anxiety of Gen-X entering adulthood, and it had real collateral. It’s expressed in Magnolia, it’s expressed in Fight Club, and it’s expressed in Being John Malkovich: that anxiety about being asked to enter a world that seemed a little bit uninviting.”

But it’s Norton’s Fight Club character—an unnamed solace seeker who dramatically reboots his own life—who discovers the hidden promise of this new era of uncertainty: “Losing all hope was freedom,” he says, and many of the filmmakers and performers from the 1999 movies could relate. Thrown together at the end of the century, and at the height of their industry’s pop-culture powers, they’d been liberated from constraints of budget and technology—and sometimes even the wishes of their bosses—to make whatever movie they wanted, however they wanted. “Maybe it was the rush of everyone thinking about the end of the world,” says Rick Famuyiwa, the writer-director of the 1999 comedy-drama The Wood. “We felt we had to get our voices heard before we all disappeared.”

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