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The 69 Best Alternative Rock Songs of 1999

20. Santana feat. Rob Thomas – “Smooth”

The crown jewel of Frankenstein celebrity collabs, “Smooth” absolutely should not have worked out, but went on to break records: As a standalone single, the pairing of Rob Thomas and Santana has charted higher than any Madonna, Michael Jackson or Beatles song, officially becoming the second biggest single of all time. Something about its outright shamelessness has endured in the face of changing trends. From Santana’s over-the-top guitar to Thomas’ egregious attempt at sex appeal, it’s just about the furthest thing from a subtle earworm—though its lyrics about falling in love in the summer heat are surprisingly complex. Santana recently recalled to Rolling Stone, “They said, ‘Why don’t you guys go to the studio and record it at the same time?’ As soon we went to the studio and I heard this sound, it was like, ‘Oh, my God, this is on a whole other level of trueness.’ It sounded true, all the way through. I knew this was very different.” — ROB ARCAND

19. Nine Inch Nails – “We’re In This Together”

Trent Reznor said that, originally, this triumphant churner was out of place for his ambitious, moody, 103-minute concept opus The Fragile. “I didn’t want a song that was too obviously the hit single,” he told German music channel Viva Zwei. “[T]he vocal track I would have thrown out that was out of tune and my voice was breaking up was the one that I needed to use, because it added a desperation that made the whole mood of the song feel right.” Though the anthemic chorus borders on “hit single,” the song still grinds with crunchy noise, whining guitars and a trash-can-sounding snare drum. — CHRISTOPHER R. WEINGARTEN

18. Beastie Boys – “Alive”

At a time when rap-rock was growing in popularity and proving to be extremely divisive, there were few artists who effectively melded the two genres as well as the Beastie Boys. While it’s not as flashy or seminal as singles like “Intergalactic” or “Sabotage,” the understated majesty of “Alive,” from their two-CD anthology, showcases the consistent brilliance of the crew as talented MCs, feeding off each other like they share one brain. Its also a record that makes sure to announce just how much they actually pioneered the idea of bringing rap and rock together: “Created a monster with these rhymes I write/Goatee metal rap, please say goodnight,” Ad-Rock spits. With great power comes great responsibility. — ISRAEL DARAMOLA

17. Lo Fidelity Allstars ft. Pigeonhed – “Battleflag”

After the Seattle punk-funk duo Pigeonhed, made up of producer Steve Fisk and vocalist Shawn Smith, released 1996’s The Full Sentence, their A&R rep masterminded the remix album Flash Bulb Emergency Overflow Cavalcade of Remixes, which contained the self-proclaimed “punk-paste” outfit Lo-Fidelity All Stars’ strobe-lit reworking of basement-show roof-raiser “Battleflag.” Its heavy grooves, casually violent video and Smith’s manic-preacher vocal helped propel it to No. 6 on the Modern Rock chart. And it all happened virtually: “I’ve never met the Lo-Fidelity All Stars,” Fisk said in a 2014 interview where he described the song’s genesis. “They tried to sue us for the publishing when the song became a hit. … It’s a very, very interesting situation where they tried to launch their career based on the remix. Of course, they didn’t have Shawn Smith in the band, so they needed a vinyl of his vocals, and went around the country doing the remix with Shawn off of a disc. I respect the old-school technology, but … they’re kind of sleazy.” He added, “I’m very happy that the song did that well, and I wish it didn’t have to be acrimonious.” — MAURA JOHNSTON

16. Sugar Ray – “Every Morning”

Perhaps no band on this list screams 1999 quite like Sugar Ray, an act fronted by a hot guy with a goatee and frosted tips who basked in the smooth breeze of jangly acoustic guitars and canned DJ scratches. Their music’s Clinton-era optimism is most apparent in “Every Morning,” where Mark McGrath sings about having his heart ripped out despite sounding like he’s also having a nice afternoon riding a skateboard. Of the band’s iconic singles, this one is the saddest, but it also might be their most audacious. The catchiest parts of the song are the verses, while the chorus features a long wordless exhale, with disembodied voices floating in and out of the mix. If the whole song’s a hook why bother writing one, I guess. — JORDAN SARGENT

15. Blink-182 – “What’s My Age Again?”

“What’s My Age Again?” is a song about Mark Hoppus being a piece of shit and living in fear that society won’t let him be a piece of shit forever. After declining sex from his girlfriend so he can watch TV and then later prank calling her mom, he’s left single and pleading, though only half-heartedly: “No one should take themselves so seriously / with many years to fall in line,” he sings, “Why would you wish that on me?” Alas for Hoppus, this death-grip on immaturity is belied by he and his band’s insanely good songwriting, which pairs this tantrum to an arrangement that shifts back-and-forth from gentle shimmer to pop-punk snicker as smoothly as the sports cars they surely ended up driving after Enema of the State went five times platinum. — JORDAN SARGENT

14. Korn – “Freak on a Leash”

Korn’s whiny guitar line, life “always be messing with me” grievances, and exorcistic beatbox interlude helped smuggle mid-tempo rap-conscious gruel rock to the upper reaches of the Hot 100. Nu-metal’s biggest hit went so mainstream that conservative pundits are performing it on television two decades later for laughs. Jonathan Davis said the song was a critique of the music industry, but the band abbreviated the most interesting part, that beatbox-and-guitar breakdown, to make it more palatable for the radio. Brian Welch explained the decision to SPIN: “I want a bigger house.” — TOSTEN BURKS

13. Garbage – “When I Grow Up”

SPIN described Garbage’s Version 2.0 as a “nonstop singles aggregation that’s going to make the crap glutting Modern Rock radio suck even worse.” Four singles in, “When I Grow Up” was the shiniest yet: a pulsating dance-pop song about, as Shirley Manson told the Independent, “that delirious state of wishing and hoping and dreaming for things, not giving up.” It’s also about golden showers and unprotected sex and irrational rages and being in the middle of enough mistakes to fill a juggernaut – and, more importantly, how those things, if properly arranged into the right hooks, can sound full of life. Butch Vig, as always, fills “When I Grow Up” with studio tricks, drowning every hook in distortion and frippery. (No worries: the hooks are good enough to pierce through anyway.) At the time, it was remarkable how poppy, Pro Tools-y, nearly-Spice-Girls-choreographed “When I Grow Up” was, even for Garbage. The band even called it “sci-fi.” Now, it’s standard stuff for pop stars like Avril to indie rockers like Charly Bliss to Sir Babygirl to Colleen Green, whose I Want to Grow Up recasts this for another generation’s longing to grow up and turn the tables. — KATHERINE ST. ASAPH

12. Kid Rock – “Bawitdaba”

Bob Ritchie made his first demo in the late ’80s and spent a decade in the white rapper wilderness before finally finding his redneck rock star voice on 1998’s Devil Without A Cause. The album was slow to catch on, crawling to gold in its first 8 months in stores. Then he released “Bawitdaba” and went supernova, riding the song’s explosive power chords and Busy Bee-indebted chorus of nonsense to diamond-certified sales, winning over crackheads, critics, and cynics in the process. On the song’s original demo, the lyric “get in the pit and try to love someone” was the considerably edgier “try to kill someone.” When Kid spoke to The Baltimore Sun in 1999, he seemed glad that the radio-friendly change reflected the supportive environment of the mosh pit: “You fall down, someone helps you up. It’s showing some love.” — AL SHIPLEY

11. The Chemical Brothers – “Let Forever Be”

Unabashedly copping the Beatles banger “Tomorrow Never Knows” and accompanied by Michel Gondry’s kaleidoscopic Busby Berkely video, “Let Forever Be” was a burst of psychedelic Big Beat that snuck onto rock radio during its final flirtations with electronica. Noel Gallagher on vocals may be a little too on the nose, but in a decidedly ungroovy year, it was a welcome relief from pissed-off post-grungers and hip-hop hybrids. — SEAN MALONEY