Why 1999 Was the Best Musical Year of the '90s

Backstreet Boys, 1999.
Courtesy of Jive Records

Cover for Backstreet Boys' 1999 album "Millennium."

After focusing on 1994 last week, now, we're wondering what the best year for music was of the '90s. We've already made a case for 1990199119921993199419951996 and 1997. Now here are the final two years of the decade -- 1998 and 1999.


The year 2000: the dawn of a new millennium, a time of post-Y2K technological breakthroughs, and one of the greatest years ever for albums. Kid A, Stankonia, The Marshall Mathers LP, The Moon & Antarctica, Supreme Clientele, Stories From The City, Stories From The Sea, Lift Yr. Skinny Fists…, Since I Left You, and Ágætis Byrjun (depending on where you lived in the world for that last one) — that’s an indestructible lineup of groundbreaking music, from artists whose ideas would resonate within the medium for the next decade and beyond.

But we’re not talking about 2000. We’re talking about 1999, its goofy older brother.

The final year of the 90s found the next century’s big stars making their unforgettable introductions (hi, Xtina and Eminem), but was also a bender of “How did THAT become a hit?!” zaniness that was enjoyable to anyone with a love for unpredictable popular music. 1999 was a year in which important albums (okay, okay, “important” albums) from Jennifer Lopez, Moby, Blink-182, Dido, Blaque and Ja Rule could all be released on the same day and could all find immense success, because we were still a few years away from LP sales falling off a cliff. It was also a year in which the Backstreet Boys’ Millennium could be nominated for album of the year at the Grammys, because we were still one year away from an avalanche of great albums.

Yes, 1999 included rightly acclaimed releases like Midnite Vultures, Beck’s best album (yup, I said it); The Soft Bulletin, the Flaming Lips’ long-awaited breakthrough; I See a Darkness, Bonnie “Prince” Billy’s classic folk meditation; and Things Fall Apart, the Roots’ most slicing statement to date. But it also had Significant Other, a wholly ludicrous smash from Limp Bizkit that made phrases like “nookie,” “nu-metal” and “Durst” mainstream. This was a year in which Smash Mouth’s happy-go-lucky pop-rock didn’t need a drop of irony to entrance the kids — hey now, we were all all-stars, back then. Madonna seduced Austin Powers in a music video, a band called Orgy released an industrial cover of New Order’s “Blue Monday” that was impossibly great, Lou Bega was a name everyone knew, and TLC’s “No Scrubs” resulted in an “answer song” titled “No Pigeons” by Sporty Thievz, a group forever relegated to being a correct answer at trivia night. This was the year that Baz Luhrmann, the director of William Shakespeare’s Romeo + Juliet, recorded a spoken word single that hit the Hot 100; so, yes, this year was highly ridiculous.

We could discuss the oddball artists of 1999 basically forever, from Powerman 5000 to S Club 7. Yet let’s narrow our focus down to two extremely different voices: Britney Spears and Santana. Along with BSB’s “I Want It That Way,” Spears’ “…Baby One More Time” remains the enduring legacy of the teen-pop explosion by serving as the song that effectively lit the fuse; once Brit showed up in her schoolgirl outfit, pop fans knew what the next five years of mainstream music were going to hold, more or less. The alternative revolution had come and gone, and bubblegum was back in vogue. *N SYNC would capture the zeitgeist one year later with their No Strings Attached album, but it was “…Baby One More Time” that turned everything on its head, its opening three notes now as iconic as those of the Rolling Stones’ “Start Me Up” and Spears’ teen-queen image inviting artists like Christina Aguilera and Mandy Moore along for the ride. Like so much other popular music in 1999, “…Baby One More Time” wasn’t brilliant, but it was impossible to resist.

The same goes for “Smooth,” Santana’s blockbuster collaboration with Rob Thomas that dominated the charts in the second half of the year, and, again, just a strange thing to watch happen. Unlike Latin-pop pretty boys Ricky Martin, Enrique Iglesias and Marc Anthony, Carlos Santana was in his low 50’s when “Smooth” happened, and doesn’t sing on the track. Instead, he left the vocal duties to Matchbox Twenty frontman Rob Thomas, who sings lyrics like “My Spanish Harlem Mona Lisa/You’re my reason for reason/The step in my groove, yeah,” with totally sincerity. “Smooth” was a wacky pairing that had no business crossing over, but there it was, topping the last nine Hot 100s of the century, bringing us into 2000 in the most unexpected but feel-great way possible. It was just like the ocean, under the moon; it was a sea of peculiar pop that we didn’t mind swimming in for a full year.