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The Best Songs of 1999

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As a wise man once said, the years start coming—and they don’t stop coming. It’s been 20 years since 1999, a truly weird and wonderful year for music, especially singles. MTV’s Total Request Live (aka TRL) dominated the music industry, which was defined by a new era of music video craze, high-profile personalities and pop music generally having the upper hand. Two years earlier, during her infamous 1997 VMAs acceptance speech, industry antagonist Fiona Apple called the music world “bullshit.” In 1999, she found herself with another hit on her hands. Boy bands like the Backstreet Boys and *NSYNC were pushing a new brand of inescapable slippery pop, while their female counterparts, like Britney Spears and Christina Aguilera, flew solo with help from rising pop masterminds like Max Martin. TLC and Destiny’s Child were radio hitmakers who ushered in a new chapter of R&B girl group domination. Meanwhile, the golden age of ’90s indie rock was winding down, but had another masterpiece up its sleeve in the form of an album called Keep It Like A Secret. Albums were still relevant, but singles were the lifeblood of artists in the making, which is why we decided to recap the best songs of 1999. Here are our picks, as voted by the Paste Staff. Listen to the Spotify playlist right here.

25. Dixie Chicks: “Goodbye Earl”

There are lots of amazing things about “Goodbye Earl,” the third single from the Dixie Chicks’ outstanding fifth album, Fly. There’s the well-crafted story about small-town life, domestic violence and murder that powers the song. There’s the fact that the writer of that story, Dennis Linde, also wrote Elvis Presley’s 1972 hit “Burning Love” (!), and that the “Earl” single’s b-side was an ironic cover of Tammy Wynette’s “Stand By Your Man.” There’s that incredible “na na na na na, goodbyyyyyyeee Eaaaaaaarrrl” hook in the chorus and the way the banjo kicks in at the start of the second and fourth verses. And there’s Natalie Maines’ vocal performance, which expertly walks the line between deadly serious (befitting a song about abuse) and cracking up (befitting a song about poisoning your abuser’s black-eyed peas, dumping his body in a lake and then opening a roadside fruit stand). But the best thing about “Goodbye Earl” is the palpable lifelong bond between the song’s core protagonists, Mary Ann and Wanda. When Mary Ann hops on a “red-eye midnight flight” to visit Wanda in the hospital and hatch a revenge plan, it’s a legitimate lump-in-the-throat moment. “Goodbye Earl” is an absolute blast of a song, and its central story of friendship, commitment and care resonates more than ever two decades later. —Ben Salmon

24. Pavement: “Spit on a Stranger”

Pavement’s 1999 album Terror Twilight was indeed released in the band’s twilight, marking the end of a decade in which they rode a new indie wave. When stacked up against now-classics like Slanted & Enchanted and Crooked Rain, Crooked Rain, it’s not a fan favorite. But it still feels hard-won—a band sticking with it despite having probably reached their expiration date. The opening track “Spit on a Stranger” is not as left-field lyrically as most music in Pavement’s catalogue and finds Stephen Malkus sounding surprisingly tender. “Spit on a Stranger” is proof that cynicism wears off eventually, making room for “two bitter strangers” to figure out how to peacefully coexist. Or, this is just a ruse and Malkmus is teasing all of us. Either way, the song got the bluegrass treatment from Nickel Creek a few years later, sparking a debate as to which version is better. Real “Spit on a Stranger” stans know Chris and Stephen both achieved glory here. —Ellen Johnson

23. Dr. Dre feat. Snoop Dog: “Still D.R.E.”

Perhaps the most instantly recognizable rap beat of all time, the simple guitar strums that lead off “Still D.R.E.” came to define a generation of West Coast hip-hop. The song is still ubiquitous today throughout California, no matter where on Route 1 you are, influencing every rapper to come out of the Golden State ever since. Featuring Dr. Dre and Snoop Dogg’s smooth call-and-response chorus, “Still D.R.E.” introduced the world to a new era of mainstream rap, serving as the lead single on the multi-platinum 2001, the top-selling rap album of the 2000s (despite the album coming out in November 1999). Iconic from the outset, “Still D.R.E.” is gangsta rap at its absolute best, proving that it was still possible to “perfect the beat” even after releasing The Chronic. —Steven Edelstone

22. blink-182: “All The Small Things”

With the possible exception of “Mr. Brightside,” “All the Small Things” may be the most singalong-able rock song of the past 20 years. Tom DeLonge’s slowed-down lyrics drip like molasses—“Late night / Come home / Work sucks / I know”—making this an anthem the likes of which we haven’t really seen since. This was also the first time Blink truly succeeded on a legitimate mainstream level— this became their only top 10 song to date (and their only top 40 entry as well), meaning the bratty California pop-punks were suddenly reaching an audience they never could have dreamed of, becoming icons for class clowns and troublemakers everywhere. Throw some “Na na na”s in there for good measure and “All the Small Things” will be stuck in your head for the rest of the day. —Steven Edelstone

21. Sigur Rós: “Svefn-g-englar”

At the crossroads of post-rock, dream-pop and ambient lives Sigur Rós’ wispy, 10-minute masterpiece “Svefn-g-englar.” The title loosely translates to “sleep angels” and “sleepwalkers,” and it’s taken from the Icelandic group’s classic second album, Ágætis byrjun, which celebrated its 20th anniversary this year. The only thing that will keep you from dozing off during this delicately nurturing track are the tears that will flow from its elegant, devastating sadness, which stems from the syrupy ambience, glimmering keyboards and Jón Þór Birgisson’s arresting falsetto. The track describes the innocence of a baby inside the womb, and it captures both the hope and the grand yet difficult-to-grapple-with randomness of life. It follows the album’s minute-and-a-half instrumental intro track, and it’s the perfect opener to an album which translates to “a good start.” —Lizzie Manno

20. Beck: “Debra”

Thanks to a clever and confounding placement in the Baby Driver soundtrack in 2017, this Midnite Vultures sleeper is once again on our pop culture radars. But it wasn’t always one of Beck’s seminal tracks. The sly funk song was originally meant to appear on Odelay, but Beck thought it was better suited to the left-field mayhem of Midnite Vultures. “Debra” wastes no time in getting straight to the point, with Beck making direct passes at JCPenney employee Jenny and her sister Debra via passionate falsetto. “It became the centerpiece of the whole set,” Beck said in a 2015 Guardian interview. “It was the song that people would react to more than the songs that they’d heard on the radio. So we kept playing it and playing it.” And sharing gum with girls was never the same again. —Ellen Johnson

19. Wilco: “Via Chicago”

Despite its ominous opening lines (“I dreamed about killing you again last night / And it felt alright to me”), “Via Chicago” immediately unfolds as a tender ode to the city that gave the band their start. Culled from the album Summerteeth, it’s bathed in wistful reflection, but ultimately comes across as another in a long line of Wilco escape songs, an expression of passive acceptance that finds resolution simply by returning to the place where comfort was found early on. The passive melody is eventually entangled in dissidence that surfaces and then fades as the song works its way to an otherwise unobtrusive exit. Even so, it remains one of the band’s most elegiac entries. —Lee Zimmerman

18. Backstreet Boys: “I Want It That Way”

Sure, the lyrics don’t make sense (songwriter Max Martin could barely speak English at the time). Yes, their facial hair and fashion sense is corny as hell. But I dare you not to sing along when someone chooses “I Want It That Way” at karaoke. 1999 was the peak year for boy bands, noted by *NSYNC’s first top 10 hit and 98 Degrees’ chart takeover, but Backstreet Boys’ Millennium ruled them all en route to the biggest first sales week in Nielsen SoundScan history. “I Want It That Way” was its biggest hit, the kind of song that was truly inescapable back then—and to some extent, still today. Name me a bigger key change in pop music history—I dare you. —Steven Edelstone

17. Sleater-Kinney: “Get Up”

Musically, few Sleater-Kinney songs pack as much pep as “Get Up,” from their 1999 classic The Hot Rock. The chipper competing guitars sound like they’re training for a marathon, while Corin Tucker’s singsong ranges from melodic to primal. But thematically, it’s more existential. Sleater-Kinney have spent much of their careers spitting fire into hard truths, but they also occasionally surrendered themselves to a lustrous fantasy, as they do here: “Let it all go at once / not piece by piece / but like a whole bucket of stars / dumped into the universe.” —Ellen Johnson

16. Fatboy Slim: “Praise You”

In high school, while I was finally broadening my musical horizons, one of my best friends in the world was listening to Fatboy Slim almost nonstop. I had no idea who that was, but the day he lent me an earbud, “Praise You” became an instant hit for me. I had never heard something with that amount of pure, unbridled joy or the gumption to stretch, squish, and color its musical components the way Fatboy Slim had in this timeless track. —Dale Jakes

15. Magnetic Fields: “The Book of Love”

Stephin Merritt makes great use of his sonorous voice to authoritatively put forth a kind of manifesto, as he’s called it, for 69 Love Songs. As manifestos go, this one is unusually enchanting. Every idea in the song is irresistible. The notion of The Book of Love is where music comes from is wonderful and pushes things into the realm of magic realism. You have to imagine this encyclopedia of the heart, which contains such wonders, as something that could not possibly exist in the physical world, but what if it did? Who wrote this Book of Love? It might be mostly boring, but who wouldn’t at least like to get a peek at a few of those things “we’re all too young to know?” The heart of the song however is the contrast between the conceit of all the tricky charts and instructions in the titular compendium with the simplicity of the melody itself and of the uncomplicated emotion it conveys. —Beverly Bryan

14. Faith Hill: “Breathe”

In the long history of ’90s ladies filming thirst-fueled and thirst-inducing music videos in the desert (looking at you, Britney, Shakira and Shania), Faith Hill shines in “Breathe,” both figuratively and so, so literally. The single rebranded Hill in a sultry departure from the previous year’s “This Kiss” (the hairstyling evolution alone!)—in addition to giving her cross-genre appeal via its blending of pop and country sounds for an infectious respiration-themed anthem. “Breathe” catapulted Hill to the pinnacle of her career, becoming only the second single to top the year-end charts despite never landing the number one spot. —Katie Cameron

13. Sixpence None the Richer: “Kiss Me”

Originally released on the first Dawson’s Creek soundtrack, Sixpence None the Richer’s smash hit “Kiss Me” is airy and romantic without approaching cheesy territory. However it was and remains a starry-eyed story of teen love, full of “sparkling silvermoons,” dancing fireflies and “milky twilights.” It’s what every ’90s kid may have dreamed their first kiss would be like. —Ellen Johnson

12. Eminem: “My Name Is”

Like many of Eminem’s best tracks, “My Name Is,” the lead single and opening track from Eminem’s major label debut The Slim Shady LP, is jam packed with one ridiculous, quotable lyric after another. It’s part satire comedy, part aggressively self-deprecating hip-hop as Eminem berates himself (“My brain’s dead weight”) and describes his difficult upbringing (“99 percent of my life, I was lied to”). It’s no wonder many of the suicidal lines and lyrics about his mother had to be removed in its censored version. His crude, absurd (and frankly problematic) lyrics matched with goofy backing vocals, a sampled groove from Labi Siffre’s “I Got The…” and Dr. Dre’s beat make for a gritty, violent self-portrait, a tongue-in-cheek, made-to-shock rap track and a piece of sheer theatrical lunacy. —Lizzie Manno

11. Blur: “Tender”

Blur combined their alternative rock percussions with the London Community Gospel choir’s gospel vocals in “Tender.” In February 2012, Blur was awarded the Outstanding Contribution to Music Award at the BRIT Awards. The English rockers performed a five song set that reunited Blur with the London Community Gospel choir to perform their 1999 hit. —Stephanie Sharp

10. Flaming Lips: “Race for the Prize”

Truly, any track off The Flaming LipsThe Soft Bulletin would be a worthy addition to this list; it’s a marvelously dreamy and deeply emotional sonic journey. But the upbeat “Race for the Prize” really does hone in on that very Flaming Lips-ish juxtaposition of soaring accompaniment and existential lyrics. Set to an incredibly layered background of percussive wonderment, we find two scientists racing for the good of all mankind, side by side, so determined. Their pursuits to forge into the future may kill them, these regular humans with wives and children, but there’s hope against hope. The easy singalong nature of “Race for the Prize” makes it one of the most memorable songs from The Soft Bulletin, examining the price of discovery (here, perhaps, of the atomic bomb). But even more generally, Wayne Coyne’s lyrics restore humanity and pathos to ordinary people doing extraordinary work, giving true stakes to forgotten toil. It was beautiful then and now. “Upwards to the vanguard!” —Allison Keene

9. Cher: “Believe”

Let’s get one thing absolutely straight: T-Pain would be nothing without our lord and savior Cher and her ‘99 Auto-Tune bonanza “Believe.” Her voice? Unearthly. Her feminist message? Just as relevant 20 years later. Released off her 22nd solo studio album (!!!), the single made heavy use of the then-unheard-of vocal technology to revitalize Cher’s music career. When her record company requested that the distortion effects be removed from the track, she responded—in iconically Cher style—“Over my dead body.” We, and everybody else who’s been singing “Believe” in the shower for the last two decades, couldn’t be more grateful. —Katie Cameron

8. Foo Fighters: “Learn To Fly”

The lead single from 1999’s There Is Nothing Left to Lose came accompanied by a goofy video, arguably Foo Fighters’ most famous, in which each member plays various characters (with Grohl’s excitable fangirl being a particular highlight). Also starring regular partner-in-crime Jack Black and his Tenacious D bandmate Kyle Gass, the Airplane-inspired promo not only gave the band the first of their 10 Grammy awards, but it also helped the Foos break into the U.S. Top 20 for the first time. “Learn To Fly” doesn’t exactly break new territory, but it’s the sound of a band at the peak of their rousing chart-friendly powers. —Jon O’Brien

7. Fiona Apple: “Fast As You Can”

Those DRUMS. Those KEYS. The intensity of this song’s intro paired with a series of fast-talkin’ warnings gives “Fast As You Can” its overall feeling of urgency, something Fiona Apple has excelled at from Tidal’s rumbling lead-off track “Sleep to Dream” all the way to the see-sawing “Periphery” on The Idler Wheel…. Released somewhere in the middle of Apple’s high-profile relationship with Paul Thomas Anderson, the song immediately fell victim to hearsay. It’s hard to listen to the song today without thinking about the Apple/PTA junction, a fiery partnership between two creators who never figured out how to tame the wild love that’s so acutely described in When The Pawn…. The song is a perfect snapshot of those feelings, as well as a rousing anthem for anyone who’s ever felt tired and trapped in a relationship. —Ellen Johnson

6. Destiny’s Child: “Say My Name”

Not only is “Say My Name” one of the best songs of 1999, it’s also one of the best songs of the ’90s, and maybe even one of the best ever modern pop songs. Instantly recognizable and always iconic, the shimmery R&B earworm from The Writing’s On The Wall is as entwined with American pop culture as Beyoncé herself. “Say My Name” didn’t peak on the Billboard charts until spring of 2000, but it was somewhere on the charts for a total of 32 weeks—and forever in our hearts. —Ellen Johnson

5. The Roots feat. Erykah Badu: “You Got Me”

Things Fall Apart marked a quantum leap forward for The Roots, but the album’s most consequential track was buried near the end of the 70-minute masterpiece. “You Got Me,” the record’s lead single, condensed the group’s jazz-rap approach, injecting some romance into Black Thought’s steely rhymes and resulting in one of the great hip-hop love songs of the ’90s. It also introduced the group’s propensity for bringing out the best from all manner of guests, especially peers in the Soulquarians scene. In fact, Roots lore holds that Jill Scott was supposed to sing this song’s killer hook (she co-wrote the damn song), but was replaced with Erykah Badu when label brass insisted on a bigger name. It would be hard to deny that Badu delivers the requisite sly vulnerability. And at least Scott got her rightful due on Phrenology three years later. —Zach Schonfeld

4. Smash Mouth: “All Star”

“All Star” was not always a car commercial; it was once the best reason to listen to top-40 radio in 1999. It begins with the message that most of us get from junior high school—“Somebody once told me the world is gonna roll me”—and heightens that anxiety with a jittery ska beat, hip-hop scratching and a half-sung/half-toasted vocal. So the tension is pretty tight when the rock ‘n’ roll guitars come crashing in with the chorus, cutting that stretched-out rubber band and setting loose a rising, anthemic vocal that promises every picked-on 13-year-old, “Hey, now, you’re an all star.” The lyrics would be trite if the surging rhythmic momentum and dizzying melodic changes didn’t make you feel like the surprise write-in candidate of the National League’s mid-season balloting. And it wasn’t merely the best example of Smash Mouth’s recurring habit and channeling of that old Beatles/Beach Boys promise: If you fuse melody and rhythm into an inseparable, galloping hook, you can capture the thrill of adolescence. —Geoffrey Himes

3. Britney Spears: “...Baby One More Time”

It’s borderline unbelievable that Britney Spears’ debut single was “...Baby One More Time.” The song is nearly an embodiment of the late ’90s, with the 18-year-old Spears emerging on the scene as the fully-fledged femmebot of our teenage dreams. Passed over by TLC, Spears’ longing but hyper-precise vocal delivery easily turned the single into one of the catchiest pop hooks of the decade. Via “...Baby One More Time,” any traces of Spears’ Mouseketeer persona were shed as quickly as the bottom halves of her shirts. In the equally iconic music video, she dons pigtails and a Catholic schoolgirl uniform to combine girl-next-door sweetness with a distinctly sexual edge (in case you missed it in the literal song title). —Katie Cameron

2. Built to Spill: “Carry The Zero”

For more than a quarter of a century, Built to Spill’s Doug Martsch has been expertly marrying melodic indie-pop and transcendental guitar jams, and nowhere is that marriage more harmonious than on “Carry the Zero.” Over the course of five minutes and 44 seconds, Martsch and company transform the song from gentle, jangling, singsong lullaby to a dancing fountain of six-stringed heroics that fade out into forever. The peak (and the pivot) is the song’s bridge, which features Martsch offering typically wary wisdom through a roller-coaster melody: “You’re so occupied with what other persons are occupied with and vice versa,” he sings. “You’ve become what you thought was dumb, a fraction of the sum.” And then the song blasts off into the best two-minute stretch of one of the greatest electric guitar albums ever made. It’s a close-your-eyes-and-get-lost moment from a guy with more than a few of those on his resume. —Ben Salmon

1. TLC: “No Scrubs”

After a four-year absence in which the TLC story only became even more turbulent, the group had to come back with something mightily impressive to reclaim their throne. They did, and then some. Backed by a suitably futuristic promo, “No Scrubs” didn’t sound like anything else circa spring 1999, and ushered in a wave of girl power anthems putting deadbeat men in their place (see: Destiny’s Child’s “Bills, Bills, Bills” and Pink’s “There You Go,” both of which borrowed that lyrical theme and harpsichord hook). Since its release, “No Scrubs” has inspired a hit answer track (Sporty Thievz’ “No Pigeons”) a hit tropical house cover (Le Youth’s “Dance With Me”) and inadvertently contributed to Ed Sheeran’s unfathomable world domination. Also boasting Left Eye’s most quotable and impossibly addictive rhymes—which were bizarrely left off parent album FanMail—it’s little wonder that “No Scrubs” has left such a lasting legacy. —Jon O’Brien

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