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The Best Album of 1999 Was … Y2K Paranoia

“Will 2K.” ‘Millennium.’ ‘FanMail.’ In a moment suffused with nervous excitement and vaguely apocalyptic grandiosity, pop music was on the brink of something, even if no one knew exactly what.

Getty Images/Ringer illustration

Welcome to 1999 Music Week, a celebration of one of the most interesting, vivid, varied music years ever. Join us as we count down the best singles and albums of the year, remember the days of scrubs and the girls who wear Abercrombie & Fitch, and argue about which albums stood above the rest.

Has anyone ever been as excited about anything as Will Smith was about the coming of the new millennium? In September 1999, he released an exuberant, Clash-sampling single destined to age like a pair of plastic NYE glasses: “Will 2K” was an ode to the rapidly approaching moment when the clocks would strike midnight on New Year’s Eve and usher us into a brave, new world of partying. “What’s gonna happen? / Don’t nobody know,” Smith shrugged, painting a scene of possible PG-rated mayhem but unquestionable fun: “We’ll see when the clock gets to 12-0-0 / Chaos, the cops gonna block the street / Man who the hell cares? / Just don’t stop the beat!” Stay jiggy, my friend.

“Will 2K” was, of course, a riff on “Y2K,” which began as a name for a computer bug that some people feared would wreak havoc on our ever-digitizing world. But in a larger sense, by 1999 “Y2K” had become a kind of catchall term for all of the giddy, existential panic surrounding the arrival of the new willennium—excuse me, millennium. Twenty years ago, computers were normalized enough to be a part of most people’s daily lives, but they were still novel enough to inspire a vague fear. “It seemed reasonable to many that there was a price to pay for all the rapid technological changes,” the artist and former Kickstarter CEO Perry Chen told BOMB Magazine a few years ago, when interviewed about his archival project on the Y2K scare. “It was also nested in a moment (the late 1990s) where we were trying to deal with this huge technological shift—the real-deal arrival of the internet, cellphones becoming ubiquitous, and the related mania of the U.S. stock market’s tech bubble.” One of the most surreal aspects of Chen’s 2014 archival project, Computers in Crisis, is a gallery highlighting covers of books about Y2K. They include titles like Facing Millennial Midnight, The Just-in-Case Food Pantry: A Common-Sense Guide for Y2K or Any Other Emergency, and, my personal favorite, Y2K for Women: How to Protect Your Home and Family in the Coming Crisis.

In the rearview, Y2K anxiety looks hilariously overblown. We all know that the story ended not with a bang but a whimper: The clock struck midnight, the world did not end, and nothing really felt that different at all. The just-in-case food pantry was left untouched.

But something unique about the music and pop culture of 1999 is that it’s eternally frozen in that moment before the millennium turned, suffused with all the nervous excitement and vaguely apocalyptic grandiosity that implied. Most of this music wasn’t as literal about it as “Will 2K” (actual lyric: “Dick Clark, holding it down”) but it still had a (retro-)futuristic implication that we were on the brink of something, even if no one knew exactly what.

Ever the visionary, Prince set the tone all the way back in 1982—a solid 13 years before the term “Y2K” was even coined. The iconic title track of his first album with the Revolution, 1999, is a swirling, synth-driven dream of imminent judgment day (“The sky was all purple / There were people running everywhere”) and celebrating like there’s no tomorrow. (Yet another concept Prince anticipated: YOLO.) “1999” certainly turned up the camp. The long, album version of the track begins with a low, ominous alien voice unconvincingly assuring the listener, “Don’t worry … I won’t hurt you … I only want you to have some fun.” But just the same, there’s a real, creeping dread to this perennial dance-floor banger; the stakes are higher than in Will Smith’s edgeless rendering of a similar feeling. “I don’t wanna die / I’d rather dance my life away,” Prince sings, cementing the connection in the pop-musical imagination between 1999 and the beginning of the end of the world.

When 1999 actually did roll around, the year’s highest-selling album was called—what else?—Millennium. The Backstreet Boys’ third album hit at the peak of the boy-band boom and the moment just before Napster, selling an astonishing 1.13 million copies in the first week of its release and topping the charts for 10 nonconsecutive weeks. It opens with the skronky, over-the-top self-fulfilling prophecy “Larger Than Life,” and the song’s TRL-topping music video was awash in millennium imagery. The opening seconds show a clock ticking down to midnight on January 1—only to show the date flipping to the year 3000. Apparently, one millennium from now, Nick Carter will be a Transformer, Howie Dorough will sleep each night in a cryogenic chamber, and Brian Littrell will skate around on a hoverboard through an undisclosed location that may or may not be the set of Tron. Looks fun!

The coming of the year 2000 meant the arrival of The Future, and the Y2K aesthetic took this idea and ran with it all the way to the moon. GQ’s Erin Schwartz recently wrote about the resurgence of “Y2K fashion,” and she cited futurism as its most defining characteristic. “The tech reckoning that never came to pass instilled relief, but also cynicism about the market forces that had produced the scare,” she wrote. “This all feels familiar today, which is why it can be fun—even cathartic—to own a piece of an era that was both very excited about the sexy, high-tech future and also already kind of trolling itself.”

That’s the exact vibe that Charli XCX and Troye Sivan capture in the lovingly detailed music video for their 2018 single “1999.” It’s an anthem of Y2K nostalgia, even though during the year in question Charli and Troye were 7 and 4 years old, respectively. Still, to them, “1999” as a concept represents a time when technology was exciting rather than exhausting: “Yeah, I remember back home / Best friends, all night, no phone, no cares,” Sivan sings. The characters they play in the video—like Charli’s Steve Jobs, steepling her fingers over an aquamarine desktop iMac—might be disappointed to learn that their vision of the future now looks passé enough to be a punch line. But 1999 is, to them, a simpler, idealized time, like the Happy Days era was to the kids who watched that show in the 1970s.

The 1999 pop record that best predicted how communication would be altered by our tech-crazed future was TLC’s FanMail, a glitchy, brooding journey into (as a computerized voice tells us on the opening track) “life, love, and the future of music.” FanMail’s best-known single is, of course, “No Scrubs,” but more indicative of the album’s overall aesthetic are songs like the title track (“Said I got an email to-da-aaaa-y,” T-Boz sings, her digitized voice breaking up like a modern-day Skype call) or even the sassy “Silly Ho,” which features an entire rap performed by a computerized voice that sounds like an after-hours Alexa. FanMail is at times a downcast record, balancing out the techno-optimism of the day with still-prescient observations like, “There’s over a thousand ways to communicate in our world today, and it’s a shame that we don’t connect.”

Communal tragedy may not have struck at “millennial midnight,” but a sad irony of the Y2K scare is that Americans did experience a perspective-altering crisis when they weren’t expecting it, less than two years later when the 9/11 attacks occurred. In retrospect, the dividing line in the mood of pop culture of the late ’90s/early aughts wasn’t pre-and-post-millennium so much as pre-and-post-September 11. That’s the greater innocence that a song like Charli XCX’s “1999” is yearning for, the latex, bubble-gum optimism of a world that braced for the end of the world and got to keep partying after midnight. Writes GQ’s Schwartz, speculating on the reason for the recent resurgence of the Y2K aesthetic, “Referencing a moment whose glee about the future contained a certain amount of nihilism is a way to be optimistic without being naive.”

Though I’m sure I wasn’t then, I am now grateful to my seventh-grade English teacher for making me write a “Y2K Journal” in the weeks leading up to the new millennium. “A lot of people are nervous,” I wrote. “I have heard some people say that at 12:00 all the money will come out of the ATM machines. A lot of people don’t want to be in a plane at midnight. I don’t think it will be so bad.” I was right.

It is perhaps most fitting to say that I don’t remember where I was when the new millennium struck, but I do remember what I was watching on a screen. MTV’s New Year’s Eve programming that night had planned it so that, at exactly midnight, No Doubt would perform an aptly chosen cover of R.E.M.’s 1987 hit “It’s the End of the World As We Know It.” I distinctly remember a magenta-haired Gwen Stefani speeding through the song’s tongue-twisting lyrics, her lips occasionally tripping her up because this was during the era that she had braces. I did too. I was 13, vaguely nervous that some computers might crash and some systems might fail, but in that moment I was largely relieved that the year 2000 had arrived with no major fanfare and that I could go back to worrying about my garden-variety seventh-grader problems. It was the end of the world as I knew it. And I felt fine.