Following our Billboard staff-picked list of the 99 greatest songs of 1999, we’re writing this week about some of the stories and trends that defined the year for us. Here, our staff goes beyond the hits of ’99 to look at the deeper cuts that also endure: The album tracks from the year’s best LPs, which prove just as essential as the singles they surrounded 20 years later. Below is a list of our 50 favorites.
50. Foo Fighters, “Generator” (There Is Nothing Left to Lose)
It isn’t hard to imagine that Dave Grohl has some sort of backup engine that allows him to sustain injuries during shows and continue to perform, but he breaks down his inner mechanics pretty clearly on Foo Fighters’ high-powered, talk box-driven deep cut “Generator.” Though the closest the song would come to mainstream airwaves was its brief feature in the opening seconds of the “Breakout” video, it continues to be a reliable spark plug that the band has wisely kept in their live arsenal for the occasional boost. — BRYAN KRESS
49. Jordan Knight, “A Different Party” (Jordan Knight)
It remains something of a 1999 mystery how New Kids on the Block alum Jordan Knight was able to secure the writing and production services of the legendary studio duo Jimmy Jam and Terry Lewis for the majority of his solo debut, but it resulted in one of the year’s compelling, if somewhat inscrutable, pop and R&B albums. “A Different Party” is one of several off-kilter standouts, sampling the pop-funk menace of Sugarloaf’s ’70s smash “Green-Eyed Lady” and throwing some frazzled horns on top for extra mania, while Knight croons with a mischievious grin, “You won’t believe/ All of the tricks up my sleeve.” Two decades later, it kinda sounds like an early draft of the Justified blueprint. — ANDREW UNTERBERGER
48. Fountains of Wayne, “A Fine Day For a Parade” (Utopia Parkway)
Four years before “Stacy’s Mom,” New Jersey-bred Fountains of Wayne wore out its welcome at Atlantic Records with Utopia Parkway, a power-pop quasi-concept album about suburban Queens that didn’t exactly fit amongst the uber-popular nu-metal and skate-punk of the day. At its emotional core, this R.E.M.-esque sad but stately ode tells the story of a day-drinking woman who thinks the neighborhood’s gone to shit after losing her daughter to “a sacred order where they get stoned and work the earth.” — CHRIS PAYNE
47. Tom Waits, “Big in Japan” (Mule Variations)
The first sound you hear on underground troubadour Tom Waits’ 1999 set Mule Variations is a cut-up loop of furniture being busted up, before a nasty big beat and nastier one-note guitar come barging through the flophouse door. After a six-year wait, the song was a megaphone announcement that the Tin Pan Alley cum laude grad had a new arsenal of clattering sounds and collaborators, for what would become his best-selling album of the SoundScan era. “Japan” distilled Waits’ whole anti-fame persona down to a delicious hobo breakfast set to a snarling, sneering beat. “I got the sizzle but not the steak/ I got the boat but not the lake/ I got the sheets but not the bread,” he croaks on the track, mocking stars who sell out overseas. “I got the jam but not the bread.” — GIL KAUFMAN
46. Dido, “Honestly OK” (No Angel)
Today, we may think of Dido primarily as a patron saint of Adult Contemporary, but on 1999 debut album No Angel, she was closer to the missing link between alt-pop sophisticates Everything But the Girl and trip-hop miserablists Portishead. “Honestly OK” is a clear highlight, with a slow-and-low beat, proto-Gorillaz dusty harmonica, and an emotionally exhausted Dido Florian Cloud de Bounevialle O’Malley Armstrong asserting with palpable world-weariness: “I just want to feel safe in my own skin/ I just want to be happy again.” — A.U.
45. Macy Gray, “I Can’t Wait to Meetchu” (On How Life Is)
The bright neo-soul of Macy Gray’s On How Life Is had already made her a critical darling before it briefly made her a star in 2000, thanks to the massive crossover ballad “I Try.” The album’s unique spark is perhaps most clearly evident on “I Can’t Wait to Meetchu,” where effervescent horns elevate Gray to a higher plane of yearning, leaving her desperate to meet her maker: “I do my best to do right got to get to the way up high/ Love the life I’m livin’ though I’m looking forward to the day I die.” Delivered with the singer’s signature rasp, it sounds as casual and joyous as a crush making her all fumbly. — A.U.
44. Tim McGraw, “The Trouble With Never” (A Place in the Sun)
Country superstar Tim McGraw’s A Place in the Sun spawned a career high four No. 1 hits on Billboard‘s Country Airplay chart, so maybe no one really needed to obsess over what wasn’t released as a single. Still, hard to believe that “The Trouble With Never” couldn’t have made McGraw 5 for 5 — the jaunty album opener boasts one of 1999’s finest lyric constructions, with the singer pontificating all the things he could “never” do to be free of his current relationship, ultimately lamenting “The trouble with ‘never’ is that ‘never’ never works.” But the song does work, mostly because it’s clear both from the sentimental lyrics and McGraw’s audible smile that he’s better off without never anyway. — A.U.
43. Handsome Boy Modeling School feat. Roisin & J-Live, “The Truth” (So… How’s Your Girl?)
A backpacker’s delight, “The Truth” came from the very late-‘90s Handsome Boy Modeling School project, brainchild of San Francisco’s creatively twisted Dan the Automator and New York’s equally irreverent Prince Paul. The languid piano-driven beat gives a long runway to Irish singer-songwriter Róisín Murphy, at the time best known as a member of the trip-hop duo Moloko, before J-Live kicks a high-concept verse about his skills through the lens of a courtroom procedural, even offering bars in Latin. That’s right, J-Live saved Latin — what were you doing in ‘99? — ROSS SCARANO
42. The Chemical Brothers, “Got Glint?” (Surrender)
The shimmering secret weapon on side two of big beat duo The Chemical Brothers’ underrated 1999 set Surrender, “Got Glint?” arrives on a fat bass line that feels like “I Feel Love” as played by Herbie Hancock. The lurching low end anchors the song, even as it continues to mutate throughout — at least until ceding the dance floor to the transclucent synth-whistle hook that functions as its refrain. Much of Surrender either feels like late-night euphoria or morning-after (morning before?) afterglow, but sandwiched between the gauzy “Asleep From Day” and the pummeling “Hey Boy Hey Girl,” “Glint” feels like the whole experience’s connective tissue. — A.U.
41. Ricky Martin feat. Madonna, “Be Careful (Cuidado Con Mi Corazon)” (Ricky Martin)
A collab betwen the leader of the Latin pop crossover moment and the “La Isla Bonita” pop GOAT — must’ve topped the charts for months in ’99, right? Actually, “Be Careful” wasn’t even tabbed as one of the four singles from Ricky Martin’s self-titled English-language solo debut. Surprising but not inexplicable: written and produced along with Madonna’s Ray of Light collaborator William Orbit, the underplayed duet treads the same kind of aqueous mid-tempo that made that ’98 Madonna effort so bewitching but challenging, leaving “Be Careful” a better fit as a buried gem than as a top 40-slaying crossover. — A.U.
40. Slipknot, “Eyeless” (Slipknot)
After a rapid fire percussion intro and Videodrome sample, “Eyeless” descends into the typical madness Slipknot is known for, particularly in the early stages of its career: Corey Taylor’s husky shouts and malevolent, pummeling riffs that feel like a punch to the face with every hit. It’s the type of song that helped build the Slipknot brand, a lucrative entity that remains successful to this day. — KEVIN RUTHERFORD
39. Silverchair, “Emotion Sickness” (Neon Ballroom)
On the third album from Australian breakout post-grunge stars Silverchair, lead singer Daniel Johns decided to get really real about the anxiety, the isolation and even the eating disorder he’d been struggling with as a much-too-young rock star. Opener “Emotion Sickness” doesn’t just open up to fans, it practically vomits strings all over them, as sweeping violin stabs introduce the six-minute opus of catharsis, Johns mewing with no shortage of self-loathing or irony, “Sacrifice the tortures/ Orchestral tear cash flow.” Countless ’90s rock bands seemed to think their wallowing was worthy of entire symphonies — few besides Silverchair could provide evidence that it actually was. — A.U.
38. The Flaming Lips, “The Gash” (The Soft Bulletin)
The Oklahoma City oddballs swung for the celestial fences on The Soft Bulletin, an ambitious album packed with experimental, mechanical beats thundering under lyrics about life, death and what it all means. It only took the Lips nine albums before realizing that there was way more than guitars to throw into the mix, and “The Gash” is the kitchen-sink result. It opens with an operatic choir chanting, before a massive drum loop kicks in and electronic squiggles ping around a chorus bleating about never giving up, giving way to Wayne Coyne’s fragile falsetto wondering if just holding it together is possible now that all our reasons for living are gone. Yes, it’s heavy, and heady, and a bit dizzying, but in the face of life’s biggest questions, this battle hymn gives you every reason to keep fighting another day. — G.K.
37. Mary J. Blige feat. Aretha Franklin, “Don’t Waste Your Time” (Mary)
Even the strongest women cave to toxic love sometimes. Mary J. Blige’s music has served as relationship “how-to” guide for women for decades, but on “Don’t Waste Your Time,” highlight from her 1999 album, Mary, the R&B icon was actually the vulnerable one, calling upon no less an authority than Aretha Franklin for advice. The Queen of Soul became the ultimate auntie, refusing to mince words with her younger charge: “Seen it a million times before/ You shouldn’t take his stuff no more.” — BIANCA GRACIE
36. The Roots, “Ain’t Sayin’ Nothin’ New” (Things Fall Apart)
One of the less-heralded gems from the Roots’ breakthrough fourth album Things Fall Apart, “Ain’t Sayin’ Nothing New” finds lead MC Black Thought and frequent collaborator Dice Raw competing for the best lines (Tariq wins with “Chase Manhattan endorse my mic checks”) over some jazzy guitar chords and a supremely confident beat, courtesy of drummer Questlove. It was enough of a low-key monster that they busted it out at Woodstock ’99 — speaking of how things fall apart. — JOE LYNCH
35. Dolly Parton, “The Grass Is Blue” (The Grass Is Blue)
Dolly Parton’s turn-of the-century move toward bluegrass (reaching back to her Appalachian childhood) might not be her best-known stylistic reboot, but it’s one of her most satisfying, thanks to 2001’s Grammy-winning The Grass Is Blue. The title track, one of two new songs she wrote for it, is a quietly devastating story of “crossing into the realm of insanity’s bliss” to avoid the reality of getting dumped. With slow banjo pickin’, a mournful fiddle and her delicate, quivering vocals, Parton entered the 21st century as vital as ever. — J. Lynch
34. Smash Mouth, “Who’s There” (Astro Lounge)
Few would’ve guessed that Smash Mouth had the juice to escape one-hit wonder status following the pop-rock ubiquity of “Walking on the Sun,” from 1997’s otherwise unremarkable Fush Yu Mang. But ’99 follow-up Astro Lounge showed that the group had the songs to do so, even before it got to the hits: opener “Who’s There” is a delightfully nervy power-pop banger with ’60s psych-pop production flourishes and a lyric about keeping an eye on the skies that feels surprisingly open-hearted for the era of The X-Files and Independence Day. BTW, a bonus suggestion if you’re looking for more So-Cal new wave throwbacks from I Can’t Believe They’re Not OHWs: Sugar Ray’s “Personal Space Invader.” — A.U.
33. Britney Spears, “Deep in My Heart” (…Baby One More Time)
Britney Spears didn’t start making club music in earnest until a little later in her career, but here she was already in full house diva mode, singing about her one true love over some giddy piano chords and an immaculate key change, as if she’s auditioning to be the fifth member of Ace of Base. Like everything on Spears’ debut album, “Deep in My Heart” sounds very much of its time — perhaps because that album defined so much of its era — but don’t call it dated: those exuberant keyboards and strutting bass line, especially during the breakdown just after the two-minute mark, would sound right at home on something like Robyn’s retro-futuristic Honey. — NOLAN FEENEY
32. Le Tigre, “My My Metrocard” (Le Tigre)
Following the breakup of her seminal riot grrrl punk band Bikini Kill, Kathleen Hanna made her way to New York City and started a new trio, the more electronic-driven Le Tigre, along with Johanna Fateman and Sadie Benning. But before the band had even officially started, Hanna and Fateman wrote “My My Metrocard” one summer on an Ensoniq Mirag keyboard sampler. An organ groan is joined by an electric guitar, a tambourine and a bopping rhythm that makes riding the New York City subway seem gleeful, that little plastic card like a ticket to freedom. Since it’s a Le Tigre song, there’s social commentary amid the bopping — including a callout of then-mayor Rudolph Giuliani, “a fucking jerk” who “shut down all the strip bars” — but then it’s back to the joyous, shout-along chorus. Next time you’re crushed in a subway car during your morning commute, your nose inches from your neighbor’s armpit, turn this on and enjoy the ride. — CHRISTINE WERTHMAN
31. Ol’ Dirty Bastard feat. Lil Mo, “Good Morning Heartache” (N—a Please)
ODB never met a stop sign in life that he couldn’t run through, or into and over. How about covering a Billie Holiday ballad from 1946 that had previously been taken on by everyone from Diana Ross to Dinah Washington and Sam Cooke? Done. On his final official solo album before his untimely death in 2004, Wu-Tang’s court jester made the ridiculous truly sublime by scatting and crooning the iconic song’s yearning lyrics (along with duet partner Lil Mo) in his inimitable way, for a soothing, oddly contemplative break after less poignant tracks such as “I Want Pussy” and “Dirt Dog.” Are you laughing with or at ODB? It doesn’t matter, because “Heartache” will touch you just right either way. — G.K.
30. Nine Inch Nails, “The Big Come Down” (The Fragile)
Nine Inch Nails’ 1999 double-LP set The Fragile failed to spin off an iconic alt-rock perennial on the level of Pretty Hate Machine‘s “Head Like a Hole” or The Downward Spiral‘s “Closer,” but across 23 tracks and nearly two hours, there are plenty of jewels to be unearthed. “The Big Come Down,” crashing in three tracks from the end, keeps you from mentally etcetera’ing the set’s final bend with its broken-glass beat, stinging guitars, and hurled vocal, whose visceral atonality makes room for a soothing, if still lyrically claustrophobic, chorus hook from leader Trent Reznor: “There is no place I can go, there is no way I can hide/ It feels like it keeps coming from the inside.” — A.U.
29. Backstreet Boys, “The Perfect Fan” (Millennium)
After the iconic “I Want It That Way” music video depicted Backstreet Boys’ sobbing fans and their adoring handmade signs, BSB capped their superstardom-cementing Millennium LP with a tearjerker called “The Perfect Fan,” which actually is dedicated to the boys’ biggest supporters — their mothers. Even the most cold-hearted pop fan has to break down a little bit when the five guys take turns shouting out their moms (“Mom, you always were…“) in the album’s final minute. — JASON LIPSHUTZ
28. Shelby Lynne, “Thought It Would Be Easier” (I Am Shelby Lynne)
If you remember singer-songwriter Shelby Lynne’s I Am Shelby Lynne album for one thing 20 years later, it would probably be how it propelled Lynne to a surprise best new artist win at the 2001 Grammys. Still, listening to the set in 2019, it maybe shouldn’t have come as a shock: the album’s sublime blue-eyed soul and pro’s pro instrumentation reminds of nothing more than one of the ultimate Grammy darlings of a decade earlier. Post-breakup lament “Thought It Would Be Easier” offers casually devastating narration (“I found that old shirt you used to wear, and it really brought me down/ Ooh does she like blue like I do?”) with a pained, whaddya-gonna-do sigh, over the saddest bossa nova beat you’ve ever heard — with keys from future country superproducer Jay Joyce, of all people. — A.U.
27. Slick Rick, “2 Way Street” (The Art of Storytelling)
The Ruler had long trained fans to expect the unexpected with his freaky tales, but “2 Way Street” (from aptly named 1999 comeback set The Art of Storytelling) delivers the biggest twist of all: monogamous devotion. The narrative finds the rapper behind “Treat Her Like a Prostitute” in two temptation scenarios, both times catching himself in a moment of guilty conscience right before cheating on his wife back home — wisely advising listeners to realize that if they want to build a meaningful relationship built on trust, “realize early its a two-way street.” Of course, if you think this means Slick Rick was going family-friendly in his old age, a listen to later track “Adults Only” ought to clear that up real quick. — A.U.
26. Christina Aguilera, “So Emotional” (Christina Aguilera)
The year 1999 opened the floodgates for blonde-haired female singers to take over what remained of the decade’s teen-pop revival. We all know their names, but there was one girl who opted for a sound a little less sticky than straight bubblegum pop. Christina Aguilera’s admiration for R&B spilled into “So Emotional,” a laid-back groove from her self-titled debut, with a title borrowed from her idol, Whitney Houston. From the lyrical tug o’ war (this guy can’t decide if he’s hot or cold) to the soulful piano melodies, the alluring track was more on par with SWV than Britney Spears. — B.G.
25. Rage Against the Machine, “Calm Like a Bomb” (The Battle of Los Angeles)
Rage Against the Machine’s 1999 album The Battle of Los Angeles ripped whatever flannel was left of the grunge era to shreds. “Calm Like a Bomb” — a.k.a. the best song that wasn’t the single — starts off inconspicuous, with just a few bass notes and whispers. Then out of nowhere, frontman Zach de la Rocha blasts through your eardrums with his signature growl: “FEEL THE FUNK BLAST!” From the intense political messages woven throughout (“There’s a ditch full of bodies, the check for the rent”) to guitarist Tom Morello’s head-rattling use of the whammy pedal, it’s a wonder how this song was never detonated on radio. — B.G.
24. Method Man & Redman, “Blackout” (Blackout)
Method Man and Redman both understand how to start a party — be it in a stoner comedy, or on a pop star’s scandalous single — and the title track of their excellent first joint album does just that, an extravaganza of grimy street rap that welcomes the listener after the album’s intro. “Da Rockwilder” and “Tear It Off” received the radio play, but neither has Redman boasting, “I scored 1.1 on my SAT, and still push a whip with a right and left AC.” — J. Lipshutz
23. Dixie Chicks, “Don’t Waste Your Heart” (Fly)
The Dixie Chicks’ Fly was such a strong album that half the damn thing was released as a single — six of the album’s 13 tracks were top 10 hits on Billboard‘s Country Songs chart, and “Goodbye Earl” wasn’t even one of ’em. The tracks that didn’t hit radio certainly weren’t held back for reasons of quality, though, and “Don’t Waste Your Heart” is a prime example: A gentle, empathetic entry in the ‘get away because I’ll break your heart’ canon, this is the album’s emotional counterpoint to snuffing out Earl or riding in the “Sin Wagon.” Even so, this nugget was just a shade too traditional country to become yet another Fly smash. — J. Lynch
22. Nas feat. Aaliyah, “You Won’t See Me Tonight” (I Am…)
Though Aaliyah’s time on earth was too brief, she still managed to worked with a slew of veterans, including Nas. For his I Am… album, the Queens MC linked with Baby Girl and her regular collaborator Timbaland for his grossly underrated gem “You Won’t See Me Tonight,” with the soft-spoken R&B legend providing the song’s unforgettable kiss-off chorus. On the verses, Nas plays a skillful lothario eager to hit the eject button on clingy women clamoring for a relationship. For Nas, chasing the bag was always priority number one. — CARL LAMARRE
21. Underworld, “Cups” (Beaucoup Fish)
Beaucoup Fish was U.K. dance trio Underworld’s best-selling album worldwide, and from the set’s opening run, you’d think it was their best album too. The singles are frontloaded on the LP’s A-side, but the best song of all might be the album cut it kicks off with: the nearly 12-minute anthem “Cups,” which begins as an entrancing two-chord deep house saunter, hypnotizing listeners for eight minutes before unexpectedly evolving into a synth laser showdown for its final quarter. Fish doesn’t live up to “Cups,” but to be fair, only a handful of dance albums in history do. — A.U.
20. Fiona Apple, “I Know” (When the Pawn…)
While Fiona Apple’s When the Pawn… opens with the rambunctious, keys-pounding “On the Bound,” it closes with the more languid, lounge-style “I Know.” Apple slowly drifts through her piano part, backed by gently brushed drums as her she softly coos about patiently waiting on her paramour, who is in another relationship. The song has no chorus, but when the strings slide in and flesh out the middle, “I Know” reaches its sonic peak, and its clearest lyrical moment, with Apple admitting, “Baby, I can’t help you out/ While she’s still around,” as the music dies down. This January saw a reworked version of the song by Apple and King Princess, which moves just as slowly, though the bigger dynamic changes in Apple’s original give it that extra emotional swell. — C.W.
19. “Weird Al” Yankovic, “Albuquerque” (Running With Scissors)
“Albuquerque” is a trip, man. Years before his nearly 11-minute-long “Trapped in the Drive-Thru,” Yankovic’s song named for New Mexico’s state capital set the standard for Yankovic opuses. The Running With Scissors closer finds the parody master at his most purely unhinged — like someone gave our guy five cups of coffee, hit record, and just let him riff until he ran out of breath. It’s long, it’s winding, it generally makes little sense strung together, and Big Sauerkraut was never quite the same afterward. — K.R.
18. Missy Elliott feat. Eminem, “Busa Rhyme” (Da Real World)
Missy and Eminem were two rappers whose universes were so much their own that it’s sorta weird to think of them overlapping. The dissonance might’ve prevented Da Real World‘s “Busa Rhyme” from being pulled as one of the album’s singles — not like it really needed help in that department anyway — but it remains a killer comic-book crossover. Over a bleating Timbo beat, a typically unhinged Em boasts about being a “stick figure with a dick bigger than Mark Wahlberg,” as Missy eggs him on as hype woman, “We gon’ get high, we gon’ roll to Vegas/ Me and Slim Shady on some shit daily.” — A.U.
17. Red Hot Chili Peppers, “Porcelain” (Californication)
Red Hot Chili Peppers’ divergence from their funk-punk sound on 1999’s Californication was perhaps contrasted best by the delicate hush of “Porcelain.” Led by frontman Anthony Kiedis’ intimate lyrics and subdued delivery, the song fashions the band’s singular skills, from guitarist John Frusciante’s spellbinding flourishes to Flea’s serpentine bass accents, into a rare minimalist production that hints at the melancholic depths explored on their follow-up By The Way. “Porcelain” remains a pivotal piece in the band’s reinvention that continues to inspire awe for listeners including Miguel, who gave it a seamless R&B treatment in 2018. — B.K.
16. Mariah Carey, “Petals” (Rainbow)
You knew that Mariah’s Caution was gonna be serious when she confirmed fan hopes that it was gonna contain a personal track on the level of “Petals,” the Rainbow cut most cherished by longtime Lambs. Containing what the singer-songwriter has called the the most honest lyrics she’s ever written, the piano ballad continues with the sound of thunder and MC offering, “I’ve often wondered if there’s ever been a perfect family,” and just gets more wrenching from there, addressing both her failed relationship with Tommy Mottola and her falling out with her sister Alison. The song’s earned musical melodrama demonstrates why Carey’s irresistible pop singles have always only been half the reason her fanbase remains so devoted nearly 30 years into her career. — A.U.
15. Hot Boys feat. Big Tymers, “Tuesday and Thursday” (Guerrilla Warfare)
“Tuesday and Thursday” is a sober warning from one huslter to another about the times of the week when the New Orleans Police Department is especially brutal. A teenage Lil Wayne bookends his verse with lynching imagery and Juvenile is as direct as possible in a closing couplet: “You wouldn’t believe the shit with the police I done been through/ I done seen some shit they did to people I’m kin to.” Manny Fresh’s production keeps the song nervous and jumpy, rather than mournful; it would never set a party off, like “I Need a Hot Girl” or “We on Fire,” but that doesn’t make the message any less essential. — R.S.
14. Blur, “1992” (13)
If you only know of Blur’s masterwork 13 through the country gospel of lead single “Tender” or the jaunty indie-pop of its follow-up “Coffee & TV,” don’t expect to be even slightly prepared for the quicksand pull of squalling heartbreak ballad “1992.” Singer Damon Albarn underplays on the verses, offering in defeated self-harmony, “You’d love my bed/ You took the other instead,” and letting guitarist Graham Coxon express the brunt of the song’s hurt through his torrential guitar downpours, getting louder and louder until they become almost unbearable. But the song’s piano plod continues unabated, the brave face the song puts on, while underneath it’s the rains of Castamere. — A.U.
13. The Magnetic Fields, “Crazy For You (But Not That Crazy)” (69 Love Songs)
While his indie peers were nipping at the heels of Pavement and Neutral Milk Hotel, Stephin Merritt brushed off trends and reached all the way back to ’30s/’40s musical theater for Magnetic Fields’ masterwork 69 Love Songs. Shoegaze guitar and vibrating electronics complement the preternaturally clever wordplay on songs such as “Crazy For You (But Not That Crazy),” which harks back to Cole Porter levels of lyrical dexterity — but with a touch of the lovingly cynical, bawdy Manhattan gay bars Merritt was frequenting at the time. Feast your ears on the American Songbook-style homoeroticism of a line like “I dwelt within and went without and broke my virgin flesh/ I performed acts of devotion as if you were Ganesh” and tremble. — J. Lynch
12. Basement Jaxx, “Same Old Show” (Remedy)
Just in case you thought 4/4 dance floor release was the only game the Jaxx had to play on debut album Remedy, they swiped a hook from ’70s ska fixtures The Selecter, and put some stank in their skank, with the brazen synths and porno vocal moans of “Same Old Show.” Unlike the album’s radio-ready singles, “Show” doesn’t really have a melody to speak of, instead just doubling down further and further on the hardness of its groove until it achieves a kind of punk intensity and electricity. No melodies doesn’t mean no hooks, anyway, as a sampled KRS-One will attest: “LET ME HEAR YOU SAY UP…. TOWWWWWNNNN!!!” – A.U.
11. Eminem, “My Fault” (The Slim Shady LP)
To answer Dr. Dre’s question more truthfully than Marshall himself: Yes, Eminem has definitely seen that one movie Kids. “My Fault” is his version of a Larry Clark x Harmony Korine youth-gone-wild parable, featuring Eminem trying to seduce a girl at a party by feeding her magic mushrooms, and then being totally unprepared to deal with it when she ODs and starts freaking out about her childhood sexual trauma. It’s just about the darkest comedy imaginable, where the joke isn’t poor Susan being stuck talking to plants, or even Eminem yelling out a shrugging “I’m sorry!” like a kid being chastized for leaving the refrigerator door open, but the unspoken implication that if parents knew the number of stories like this that occur unremarkably across the country every day, they’d never sleep again. — A.U.
10. Counting Crows, “Colorblind” (This Desert Life)
Led by the most heartstring-pulling piano riff since The Smiths’ “Asleep,” the Counting Crows’ “Colorblind” will of course be instantly familiar to any of the millions of teens for whom 1999’s Cruel Intentions was a formative viewing experience. But even without the visual of Ryan Philippe intercepting Reese Witherspoon at the top of the train station escalator, “Colorblind” is an emotional uppercut — singer Adam Duritz matches the hook for intensity, offseting his confessions of emotional ineptitude (“I am covered in skin/ No one gets to come in”) with pleas to be released (“Pull me out from inside/ I am ready, I am ready…”) Deep in the cell of his heart, he really wants to grow. — A.U.
9. Jimmy Eat World, “For Me This Is Heaven” (Clarity)
For rockers crooning about angels in ’99 mid-tempo ballads, Jim Adkins may come in a distant second in the popularity contest, but oh did he leave a legacy. “For Me This Is Heaven” is orchestral emo bliss, wide-eyed and resolute, even if it’s likely about a breakup: “When the big hand goes ’round again/ Can you still feel the butterflies?/ Can you still hear the last goodnight?” Capitol almost shelved Clarity, and only after its lead single “Lucky Denver Mint” got picked up for the Never Been Kissed soundtrack did they proceed to promote it much at all. But Jimmy Eat World’s dazzling sophomore set spawned a devoted cult fanbase, while the Arizona band searched for a label to release what would become 2001’s Platinum-certified Bleed American. Among them was Andrew McMahon, who on Something Corporate’s nine-minute “Konstantine” — a legendary deep cut in its own right — deviates from a personal love ballad to shout out his heroes: “It’s to Jimmy Eat World and those nights in my car/ When the first star you see may not be a star.” — C.P.
8. TLC, “I’m Good at Being Bad” (FanMail)
TLC’s “I’m Good at Being Bad” was initially sent out as a promotional single to ignite the FanMail hype, but unfortunately it got lost behind the shadows of the “No Scrubs” eclipse. Nevertheless, it quickly grew into a fan favorite thanks to its unadulterated rawness. It starts off innocent, as Chilli’s sweet vocals muse about kicking up sand on the ocean. But T-Boz immediately cuts all that romantic nonsense once the track switches to a Jam/Lewis-produced hardcore beat. She doesn’t have time for weakness, and expects you to “know how to lick it and stick it.” Left Eye’s final rap verse caps it all off, giving men a warning about needing a safety guide before exploring her insides. “I loved the way Kurt Cobain used to go soft and then hard, like on ‘Smells Like Teen Spirit,’” T-Boz told Billboard this year about the song’s inspiration. “So I told Jimmy [Jam] we could be like Nirvana, just sing really pretty and then go into ‘I need a crump type n—a!’” — B.G.
7. Backstreet Boys, “Don’t Want You Back” (Millennium)
Just listen to the first measure of Max Martin and Rami Yacoub’s pounding “Don’t Want You Back” beat — predating the hard-hitting pop sound *NSYNC would explore in the 21st century on No Strings Attached and Celebrity — and you’ll see why 20 years after its release and despite being passed over as a Millennium single, it remained a common sight in Backstreet Boys setlists, before this most recent tour. (No easy feat for a boy band with a discography stacked with this many recognizable bops.) Forgive the somewhat cheesy reference to their own song in the first verse, and lose yourself to the melodrama of the chorus, a breakup anthem from the Boys amid much more lovey-dovey fare of the time. — K.R.
6. Beck, “Debra” (Midnite Vultures)
Take a moment to imagine a scenario in which someone only familiar with, say, “Loser” and “Where It’s At” switches on “Debra.” Surely it ain’t the same singer, right? But no, this indeed is Beck, one of the many testaments to the troubadour’s unfettering chameleonic tendencies musically. Along with some undeniably funky instrumentation, Beck’s soaring falsetto — plus seemingly inane lyrics about JC Penney and Zankou Chicken — puts “Debra” over the edge as one of his top recordings, and explains why it worked for Edgar Wright to include it among the more traditional soul classics on the Baby Driver soundtrack. And the song isn’t even about Debra! Justice for Jenny. — K.R.
5. Jay-Z, “So Ghetto” (Vol. 3… Life and Times of Sean Carter)
With the success of Vol. 2, “Hard Knock Life” and Mariah Carey’s “Heartbreaker,” Jay-Z did the unthinkable, transforming from elite hustler-rapper to pop star. And then what did he do? Rebuked it. “So Ghetto” is the first full song on Vol. 3, a reunion of Hov and DJ Premier, the ideal producer for spitting that “murder-murder-murderous shit.” If popularity demanded middlebrow whitebread decorum, Jay was having none of it: “So I’m cruisin’ in the car with this bougie broad/ She said, ‘Jigga-Man you rich, take the durag off’/ Hit a U-turn, ‘Ma I’m droppin’ you back off.’” It really was just the same old Shawn. — R.S.
4. Moby, “My Weakness” (Play)
The final track on Moby’s sleeper blockbuster Play, “My Weakness” is unlike anything else on the album (or in pop-crossover techno at the time). A haunting piece of elegiac minimalism, “My Weakness” pairs ghostly tape loops of an African choir (“I don’t remember where it’s from,” Moby admitted to Rolling Stone years later of the sample) with quietly mournful synths Cluster might’ve played in the ’70s. It’s whispery, unsettling and utterly beautiful, and its placement at the end of an album stuffed with dancefloor fodder makes it linger uncomfortably, almost like a title card at the end of a documentary informing you the subject died shortly after filming wrapped. Bulking up its retro bona fides is the fact that it appeared in a pivotal episode of The X-Files, soundtracking the gut punch of a moment where protagonist Fox Mulder discovers the fate of his long-missing sister. — J. Lynch
3. Dr. Dre feat. Hitman, Kurupt, Nate Dogg & Six-Two, “Xxplosive” (2001)
Over one of Dr. Dre’s finest beats, some West Coast greats offer accounts of pimping so cold, Iceberg Slim would wrap his mink tighter. The iconic guitar line from Mack Browne and the Brothers’ cover of Isaac Hayes’s “Bumpy’s Lament” plays as Hittman gives a quick toast, and then Kurupt delivers one of the most spiteful verses in the Dre catalogue, a verse so spectacularly rank it forces the listener to ask, “Who hurt you?” Smoothing things out as only he can, Nate Dogg croons a velvet affirmation of his abilities and how he’s admired. But because this is “Xxplosive,” he exits rudely: “Somebody better get this bitch, this bitch,” with the last “this bitch” fading into the background, like Nate is already too weary to deal with such a frustrating scene.
As he splits, Six-2 arrives to deliver what is considered by connoisseurs — among them, Kendrick Lamar — to be one of the very best verses on the entire album. Though he self-describes as a 23-year-old pussy fiend and freakaholic, he raps with the unhurried ease of someone in the twilight of their prime — a blasé veteran of sex in ’64 Impalas and cool advocate for the pull-out method. Hailing from Fort Worth, Texas, Six-2 came to Dre via The D.O.C., and after 2001 all but appears to have evaporated, leaving us with little more than this genius turn. And that’s it. No hook. Not a single radio-friendly lyric. The title appears only a handful of times. As Nate Dogg puts it: “Real trees, chronic leaves — no seeds.” — R.S.
2. Destiny’s Child, “Hey Ladies” (The Writing’s on the Wall)
Before Destiny’s Child grew as independent women or weathered the storm to become survivors, the then-foursome were just teenagers trying to find answers of how to break the chauvinistic chains men wrapped around relationships. Why is it that men can go do us wrong? Why is it that we never seem to just have the strength to leave? The questions the girl group posed in “Hey Ladies” reflected the frustration that women everywhere felt after being stuck with a scrub for way too long. The lyrics flow like a diary entry that lead singer Beyoncé reads aloud to her closest friends, her vocals getting more fed up as she recalls all the bullshit she’s gone through: getting cheated on, her man giving the side chick money and being constantly taken advantage. No girl, listen to Kelly, LaTavia and LeToya: He’s got to go, he’s got to go. Destiny’s Child would continue to create a handful of female empowerment anthems after this, but it was “Hey Ladies” that laid the groundwork for one of the most important lessons on The Writing’s on the Wall: Thou shalt know thou self-worth. — B.G.
1. Blink-182, “Going Away to College” (Enema of the State)
This world was indeed an ugly place in 1999, particularly among rock fans. The rise of nu-metal and a backlash to both the smilng sunshine pop dominating TRL and the pro-female activism that powered the Lilith Fair combined to make macho mookishness the norm at the turn of the millennium, culminating in July’s Woodstock ’99 festival, which devolved into a hellscape of destruction and violence, with numerous cases of reported (and unreported) sexual assault. But the other biggest breakout story in ’99 rock saw the same kind of energy channeled into something much gentler and more inviting — though no less appealing to the 12-year-old boys of the world. No one would commend Blink-182 for pushing the feminist agenda with their shimmering pop-punk, exactly — Enema of the State opener “Dumpweed” proclaims “I need a girl that I can train” — but while girls were a source of regular angst and confusion for them, at least they weren’t the enemy.
You can tell, because Blink wrote fucking great love songs. “All the Small Things” became a generational pop-punk anthem about your girl unexpectedly giving you roses, but Enema roommate “Going Away to College” was just as good — a story about the titular relationship-killer, with singer Mark Hoppus hoping the long-distance thing will work even if he’s absolutely petrified that it won’t. “I haven’t been this scared in a long time,” he admits on the chorus, before offering the best 11-word valentine he can muster as a keepsake: “This world’s an ugly place/ But you’re so beautiful to me.” It’s leveling in its straightforwardness, and it’s delivered in gorgeous harmony with co-lead Tom DeLonge. And it’s songs like “College” that make it unsurprising that while the nu-metal strain has died off in popular music almost completely, not only are Blink themselves still going fairly strong, but so are acolytes like Fall Out Boy and Panic! At the Disco. Not just because they wrote perfect pop songs, but because eventually, you grow out of those days where you wanna justify ripping someone’s head off, and you just want someone to assure you that your picture is still hanging in their locker. — A.U.