The 99 Greatest Songs of 1999: Critics’ Picks

Billboard - At the end of the millennium, popular music was behaving like we really might only have one year left. You'd be hard pressed to find another year in pop history that tried to cram more stuff into 12 months: Breakthroughs, comebacks, crossovers, last gasps. Career-defining smashes that still rank among the most-karaoked songs nationwide. Bizarro one-offs that wouldn't make sense for another decade, until Twitter was invented to give them proper context. The Vengaboys. Truly, 1999 had it all. 

It'd take far more than 99 songs to summarize everything that the final year of the 20th century had to offer musically. But below, Billboard counts down our 99 favorites from the peak of turn-of-the-millennium megapop, an era of such robust sales that the RIAA had to introduce a new level of certification to account for all the new blockbusters, an era of such blinding star power that we needed Carson Daly's assistance to establish a proper hierarchy. It's time to praise 'em like we should. 

First, though, a note about eligibility: Songs were counted as eligible if they were released as singles in '99, or if they debuted on the Billboard charts in '99. But if they didn't hit the Hot 100 until the next year, or if they debuted in '99 but didn't hit No. 1 until the year after, we're counting 'em for '00. So apologies to "Say My Name," "What a Girl Wants," "Maria Maria" and several others -- we'll probably see them on this list next year. 

90. No Doubt, "New" (No. 7, Alternative Songs)

The 1999 cult classic flick Go delivered two things for Anaheim ska-punk stars No Doubt: another alt-rock top 10 hit and a seismic stylistic shift. “New” was the group's contribution to the movie’s soundtrack, a standalone single that marked a stopgap between 1995’s eventually Diamond-certified breakthrough LP Tragic Kingdom and their fourth album, 2000's Return to Saturn. Like any great No Doubt song, it’s got a chorus that can only sound good when Stefani howls it, but it’s the inventive, synth-spackled instrumentation that revealed inklings of the new wave experimentation we’d see in the next year's “Simple Kind of Life” and beyond. In short: “New” wasn’t just new, but a harbinger of things to come. -- HILARY HUGHES


1. Britney Spears, "...Baby One More Time" (No. 1, Hot 100)

Not just a career-making song, the Max Martin-helmed debut single from Britney Spears was a watershed in pop music; like similar game changers from MJ or The Beatles, there is pop prior to "…Baby One More Time," and there is pop thereafter. Minimalist in composition yet maximalist in delivery, instantly memorable yet endlessly listenable, "Baby" is a shotgun wedding between lithe funk-pop and the Swedish music machine. It's everything that absolutely should not work, yet it somehow tracks as dangerous, bold and visionary.

"Baby" was also born at the right time. Aside from Mariah, the pop titans of the '80s were never really matched during the '90s, a decade defined by alt-rock and hip-hop's ascendance. The American market was long overdue for new blood to arrive and assume the crown -- or at least throw down the gauntlet in an MTV-documented bloodbath for TRL supremacy. And with her calculated mixture of teenage naïvete and Lolita coquettishness oozing through the mic (not to mention the visual, whose concept Spears fought her director over, insisting it take place in high school vs. outer space), Britney knew exactly how to take that throne.

Twenty years later, those three piano notes are embedded in the brains of anyone who's ever come near a radio; Max Martin has left an impact on pop that rivals any studio auteur of prior generations; and Britney is still Britney, bitch. And us? Well, we still believe (still believe!). -- J. Lynch

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