There is a pair of YouTube videos I’ve been watching a lot lately. Weirdly, one them involves Fred Durst. “Yeah-yeah, baby!” he yells, his shoulders hung in a slouch, his head covered in his trademark backward red baseball cap. “Let me see them hands! Do ya feel it?” It’s footage taken just a few minutes into 1999, when Durst and his band, Limp Bizkit, were in a packed-to-capacity studio in MTV’s Times Square, playing a metallic, scratched-up version of Prince’s end-of-days hit “1999.” Hosts Carson Daly and Jennifer Love Hewitt are watching from nearby, their eyes Furby-wide with delight, while outside in Times Square, an estimated half a million people were fending off 23-degree weather and falling confetti.

They were all there to celebrate what many believed was the beginning of the end: The wind down of the 20th century, as the world prepared itself for Y2K, the supposed computer glitch that would cause chaos around the world. Planes would supposedly fall from the sky. Bank accounts would empty. The machines we’d come to depend on would undo us.

Such a cataclysm never happened, of course. (Surely a bittersweet bummer for the country’s survivalists, some of whom had readied themselves by stocking up on powdered milk and shotguns.) Yet while the grid-melting chaos of Y2K now seems, 20 years later, like a far-off, feverish hysteria, the world did undergo a massive transformation in 1999, thanks to a series of slow-release revolutions that severely mutated our lives and rewired our brains. A few months after that MTV performance, Durst and Limp Bizkit would release the hit “Break Stuff”—an unintentional anthem for a year in which so many once-impossible obstacles were done away with in nearly every artistic field imaginable.

You could see it in big-screen visions like Fight Club, The Matrix, and Being John Malkovich, which challenged multiplex moviegoers to reexamine just how much control they had over their own lives. You could see it on television, where The Sopranos reimagined what a prime-time TV drama could be. You could hear it in the aggro white-boy rap of Eminem, who shoved aside listeners’ preconceptions of race, and in the way TLC combined R&B and R&D to create the futurepop of FanMail. It was even apparent on the New York Times bestseller list, as Harry Potter books claimed the top three adult fiction spots for six weeks straight. (“I don’t think it’s really sunk in,” J.K. Rowling admitted to CNN that October. “Can you imagine what that’s like, to get out of a car and there’s a thousand people outside screaming at you? It’s amazing.”)

They were all part of a year-long creative coup that began in January with the arrival of Britney Spears’s debut album, …Baby One More Time, and ended with December’s release of Paul Thomas Anderson’s Magnolia, a jumbo-sized existential crisis that unleashed a plague of frogs on suburban Los Angeles—a possible coming attraction of the end times.

It’s impossible to gauge whether these ruptures were connected, even just ethereally, to the looming deadline of Y2K or whether it was all simply a matter of timing. But the restlessness of 1999’s popular culture was almost certainly a reflection of the changes and anxieties engulfing the world as a whole. This was the year that found the aging boomers being crankily rousted from their ’60s and ’70s daydreams, a plight best exemplified by the sight of Tony Soprano—robed, bearish, perpetually irritated—humping down his driveway each morning, dreading the day’s newspaper that awaited him. (“Lately, I’m gettin’ the feeling that I came in at the end,” Tony tells Dr. Melfi in the Sopranos first episode. “The best is over.”) And it was also a year that found Generation X eagerly if shakily assuming power—most visibly on TV, where Jon Stewart’s takeover of The Daily Show would turn the satirical news show from smart-alecky to smart.

One of the most monumental changes taking place couldn’t even be seen, as millions of Americans, no matter their age, began porting their lives over to the internet. By 1999, the web had evolved from a bumpy back road full of slow porn and iffy factoids to a high-speed creative and commercial autobahn. That year, the still-young DVD-by-mail company Netflix raised $30 million and announced a monthly subscription program. Steve Jobs stood on stage and introduced Apple users to the freedom of Wi-Fi. And Amazon’s Jeff Bezos was named Time’s Person of the Year, his head stuffed in a box and surrounded with packing peanuts.

For users, meanwhile, the internet was becoming a place where millions of voices could chime in at once—many of them anonymously—and where literal and figurative lawlessness soon took hold. (This was, after all, the year in which a startup called Napster proved a 12-song album could be reduced to a tiny jumble of “free” ones and zeroes.) Online, there were few firm realities: Was the teasing website for The Blair Witch Project a hoax or legit documentation of an into-the-woods murder spree? Am I me, or am I my Sims avatar? Millions of people were now losing themselves online—some in search of money or sex or power, but many more looking to reimagine their own existences.

It was hard to blame people for losing themselves in the perpetual fantasia of the web, when the alternative was beginning to look so unappealing. The nostalgia for all things ’90s has, in some ways, smoothed over the tumult of that decade. 1999 alone saw a series of events so far-reaching that, even today, we’re still reeling from them and re-evaluating them: Columbine marked a heartbreaking new era for mass violence and proved just how deadlocked the country had become on gun control. The flame-broiled Woodstock ’99, with its sexual assaults and misogyny, displayed a simmering young male rage that now runs rampant on social media. The impeachment trial of Bill Clinton hinted not only at the partisan scuffling and showboating that was to come, but also demonstrated the culture’s cruelty toward Monica Lewinsky — for which we’re only now making amends. And the WTO protests in Seattle that November demonstrated a deep-rooted resentment toward big corporations and unchecked capitalism that’s only grown in the decades since. No wonder some moviegoers applauded when a bunch of credit card headquarters were blown to glassy smithereens at the end of Fight Club.

Still, not all of 1999’s noisy detonations and declarations seemed quite so urgent at the time. Osama bin Laden, architect of late-’90s embassy bombings, was already on the radar of the feds and the U.N. But his ominous comments in an Esquire interview from that year—in which he warned the U.S. to change its ways, “if they value the lives of their children”—weren’t enough to raise most Americans’ threat levels. We politely ignored headlines pointing to the trouble yet to come for the housing market (“Mortgage Costs Could Ambush the U.S. Economy”) and for the environment (“Scientists Warn Against Ignoring Climate Change”). And back then, few people thought much of the political awakening of Donald Trump, whose brief fling with a presidential run found him employing the same strategy that would help him win in 2016: making cozy late-night show appearances, deriding our “very unfair” foreign trade deals, and supplying a steady stream of press-grabbing statements. “The only difference between me and the other candidates,” Trump told Maureen Dowd that September, “is that I’m more honest and my women are more beautiful.”

Trump was still pretty much a joke by the end of 1999. And soon, so was Y2K, which fizzled out sometime around 12:01 a.m. that night, the memory of the steady panic it inspired soon deleted from the country’s hard drive. But we were heading toward a new calamity—a series of them, in fact. We were just looking in the wrong directions.

It wasn’t the computers we needed to fear in 1999, but the people who programmed them: the then-younglings of Silicon Valley, who’d soon create a labyrinth of data-slurping programs that would send a plague of bots down from the sky and would act more carelessly, and sometimes lawlessly, than we could have imagined. (A teenaged Mark Zuckerberg allegedly spent part of 1999 trying to connect people via an applet called “The Web.”) And for all the tut-tutting about Clinton’s infidelity, which inspired grave fears about the “end of the American family,” the long-term damage done by the political fighting of 1999 would soon manifest itself in the Gore-Bush debacle of 2000. That was the first in a series of psyche-altering events that would soon transform the world: 9/11. Iraq. Afghanistan.

But that was yet to come. For all the dread of 1999, it managed to feel at the time like a massive, joyous, slightly nerve-wracking get-together. Perhaps that’s why it’s still possible to plug back into 1999—to re-enter The Matrix, to visit The Sopranos, to listen to Britney’s hits just one more time—with a sense of naïve delight. I do that myself sometimes, which brings me to that other YouTube clip I’ve been watching.

It’s footage of a party I went to on December 31, 1999. Thanks to my job as a young, muppety entertainment-magazine writer, I was at MTV’s studios in Manhattan, where Carson Daly was once again serving as emcee, and a ’90s-bred rock band was once again thrashing through a cover song. It had been a slow day news-wise, save for an item out of Russia, where president Boris Yeltsin had resigned, his young successor a former KGB official named Vladimir Putin. But if I or any of the partygoers packed inside the studio were aware of that, we didn’t pay it much mind. Instead, as the fireworks exploded outside over Broadway, we pressed together as No Doubt performed a track that summed up the year’s attitude and that would become a near-constant refrain in the brain for decades to come: “It’s the End of the World as We Know It (And I Feel Fine).”