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Rob Sheffield’s 99 Best Songs of 1999

Timeless classics and shameless one-hit wonders from a year when nothing made any damn sense (in the best possible way)

tlc britney blink 182 99 of 1999

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Man, it was a hot one. 1999 was the year music exploded, the year when nothing made any damn sense, the year fans had to throw out any old-school rules for how pop worked. The radio was suddenly full of shiny new stars. So many timeless classics. So many shameless one-hit wonders. So much crazed innovation, all around the margins. Teen-pop happened. Nu-metal happened. Every genre was booming. Let’s put it this way: If you spend an hour at your local karaoke bar, you’re going to hear somebody belt at least one hit from the summer of ’99. It was one of those pop moments when all that glitters actually is gold.

So let’s break it down: the 99 best songs of 1999, 20 years later. The hits, the flops, the flukes, the obscurities. Whatever type of music you loved, this year had it: hip-hop, electronica, indie rock, punk garage, country, R&B, disco sleaze. The old stylistic boundaries didn’t hold any more. “The walls came down,” as Sugar Ray’s Mark McGrath told me last year. “You would hear Kiss-FM or Z-100: ‘Coming right up, Mariah Carey, Blink-182, Eminem, Sugar Ray, and you’re like, ‘What the fuck is happening?”

Fans bought more music (with money! in stores!) than ever before or since. Nobody realized Napster was about to change everything. Carson Daly hosted Total Request Live on MTV every afternoon, where a new breed of stars got born: Britney, Xtina, Ricky, NSync, the Backstreet Boys. A previously unknown producer named Max Martin presided over the Orlandinavian connection that invaded the radio, in a strange alliance between the Swedes and the Mousketeers. Woodstock ’99 went down in flames. There was so much to hear, even great music could get lost in the rush — which is why going back means discovering new surprises. The world was cramming in as many pop thrills as possible before the Y2K crash. No rules. No shame. No scrubs.

There’s no way any list could sum up the year in a mere 99 songs — we could roll up to the thousands without running dry. As for what counts as a 1999 song, it’s all about the year of impact: Britney’s “Baby One More Time” technically dropped in late 1998, yet there’s no denying it belongs to 1999, when it conquered the world. On the other hand, Destiny’s Child’s “Say My Name” and Le Tigre’s “Deceptacon” came out on 1999 albums, but they spiritually belong to Y2K, when they went mega-nova. Cher’s “Believe” counts as a 1998 song — it was on last year’s list. (Though you could make a case it’s the song of the year, every year.)

Some of these songs turned into permanent classics, still beloved all over the world. Others come from weirdos experimenting for a tiny handful of fellow fanatics. But they all sound great today. So it’s time to celebrate the music of 1999. As a wise man once sang: Let’s don’t forget about it.