The 98 Greatest Songs of 1998: Critics' Picks

At Billboard, we're celebrating everything 1998 with a week's worth of content themed around this incredible year, remembering all the unforgettable (and some of the unfortunately forgotten) songs, artists, and moments it had to offer. To start, we compiled a list of our 98 favorite songs of '98 -- the classics that best define our memories of the year that was, and the ones that have stuck with us in the decades since. Songs were counted as eligible if they were released as singles in '98, or if they debuted on the Billboard charts in '98 -- but if they didn't hit the Hot 100 until the next year (like "Ruff Ryders' Anthem" or "Ex Factor"), or if they debuted in '98 but didn't hit No. 1 until the next year (like "Baby One More Time" or "Believe"), we're counting 'em for '99. 

See our list below -- with a Spotify playlist of all the songs at the bottom -- and have fun reliving the days of Monica Lewinsky, Jesse Camp and Mark McGwire all week on Billboard.com. 

98. Donny Osmond & Chorus, "I'll Make a Man Out of You" (Did not chart)

Let's get down to business to defeat any notion that this isn't one of the greatest Disney songs of all time. Yes, there are many racial and gender issues at play -- Osmond is providing the singing voice for a Chinese character, and the lyrics deal in a vast array of male and female stereotypes. But listening to the smooth delivery of Osmond's insults and orders to those under his charge -- and singing along with those backing "BE A MAN!"s in response -- is too damn fun to resist. -- DENISE WARNER

97. Jewel, "Hands" (No. 6, Hot 100)

Jewel successfully avoided the sophomore slump with this single, the first off her second album, Spirit. The track’s popular music video followed our star as she weirdly sauntered through the aftermath of a natural disaster, emotionless, while rescuers frantically helped victims out of the rubble. The clip wouldn’t have survived today’s relentless meme culture, but the track’s sentimental and strong lyrics hold up, and its themes echo on in modern call-to-action anthems like Pink’s “What About Us.” -- PATRICK CROWLEY

96. Nicole Wray feat. Missy Elliott & Mocha, "Make It Hot" (No. 5, Hot 100)

“Make It Hot” was a song from R&B newcomer Nicole’s debut album of the same name, but it became a hit largely because it sounded like a bonus cut off of Missy Elliott’s futuristic rap romp Supa Dupa Fly, and for good reason: Missy wrote it, Timbaland produced it, and their creeping beats and cool delivery are all over this tune. Hell, Missy even raps on the song, giving the smooth-voiced, 17-year-old Goldmind signee all the extra juice she'd need to get her alluring debut single to the top 5 of the Hot 100. -- CHRISTINE WERTHMAN

95. Cherry Poppin' Daddies, "Zoot Suit Riot" (No. 41, Radio Songs)

Amid the 1990s’ many so-called revivals of genres past, Cherry Poppin' Daddies -- and their signature hit, the unshakeable "Zoot Suit Riot" -- might be the greatest relic of the however-brief swing revival. Led by Steve Perry (no, not that Steve Perry, but can you imagine?), the band fleetingly charted in Billboard from early 1998 to early 1999 -- but what a year it was, leading pre-Google listeners to strain to remember what the Zoot Suit Riots even were (or, uh, what a zoot suit is, for that matter). Now, throw back a bottle of beer! -- KEVIN RUTHERFORD

94. Deftones, "Be Quiet and Drive (Far Away)" (No. 29, Mainstream Rock)

The "There Is a Light That Never Goes Out" of the nu-metal era, Deftones' thrashgaze masterpiece packed a generation's worth of catharsis into two chords and not very many more lyrics. The rest of their hard-rock peers spent the next half-decade trying to go forever louder and more explicit in expressing their bottomless reserves of angst, but the Sacramento quintet knew there was no point in even trying to top frontman Chino Moreno's gutturally howled, universally understood passenger-seat request: "I don't care where just FAR!!" -- ANDREW UNTERBERGER

93. Jo Dee Messina, "I'm Alright" (No. 43, Hot 100)

All of the country ladies of the late ‘90s were invested in female empowerment, but Messina’s “I’m Alright” also served as a feel-good jam that could lift anyone’s spirits. “It’s a beautiful day, not a cloud in sight/ So I guess I’m doing alright” is a timeless mood-booster, one that’s emphasized by Messina’s confident singing and the song’s breezy tempo -- all of which make “I’m Alright” a classic for fans of country and pop, whose worlds weren't that far removed in '98. -- TAYLOR WEATHERBY

92. Puff Daddy feat. The Notorious B.I.G. & Busta Rhymes, "Victory" (No. 19, Hot 100)

One year and eight days after Christopher Wallace passed, his friend and partner Sean Combs released the final single from Combs’ blockbuster album No Way Out. “Victory” is the first song proper on Puff Daddy’s debut, and it’s a monster, the sort of opener that could just as easily function as the closer, the kind of spectacular experience that demands an eight-minute long video with cameos from Danny DeVito and Dennis Hopper. The Rocky sample, the strings and ringing bell ratcheting up the tension, Puffy talking his shit over ad-libs from Big that sound like sparring before the title bout. And then Biggie arrives with the resplendence of a boxer emerging from the corner with terrifying poise and intention: “In the Commission, you ask for permission to hit 'em.” Everyone except Big, that is. -- ROSS SCARANO

91. JYP, "Honey" (Did not chart) 

After starting off with one of the most iconic, whining intros in K-pop history, J.Y. Park’s “Honey” exudes confidence with its funky brassy riff and explosive horns. This Park song became an instant K-pop classic in 1998, and even though he’s now more known as the founder of JYP Entertainment, home to the likes of TWICE and GOT7, the legacy of “Honey” lives on with countless covers by K-pop’s most popular acts. -- TAMAR HERMAN

90. Rob Zombie, "Dragula" (No. 6, Mainstream Rock)

Own a PlayStation in the late '90s? Then you were eminently familiar with "Dragula," which became part of its fair share of racing simulations in the console's early days. And with good reason: Aside from perhaps Molly Hatchet's "Flirtin' with Disaster," there's no better song to soundtrack racing games both then and now -- and c'mon, it's literally named for a drag-racing car from The Munsters. To boot, it was fitted with one of nu-metal's choicest choruses, plus riffs that absolutely kicked your ass every time out. An adrenaline rush in song form. -- K.R.

89. Shakira, "Ciega, Sordomuda" (No. 1, Latin Songs)

Shakira was a Latin American star, until she released Dónde Están los Ladrones? and crossed borders into international success. “Ciega, Sordomuda,” a pop-rock anthem that defiantly equated total love to being blind, deaf, and mute, broke completely with everything popular Latina musicians had been doing up to that point. It would become Shakira's first No. 1 on Billboard’s Hot Latin Songs chart, and the precursor to her game-changing crossover success in English. -- LEILA COBO

88. Blink-182, "Josie" (Did not chart)

In the late ‘90s, Blink-182 was writing pop-punk gospel for the post-Gen X’ers too young to remember Dookie but cool enough to realize alt-rock could be a lot edgier than Sugar Ray and Eve 6. Dude Ranch’s “Dammit” broke them in ’97, and a year later, this buzzsaw single off their major-label debut cemented the Blink brand: slapstick vocal interplay between Mark Hoppus and Tom Delonge, rapid-fire percussion (from pre-Travis Barker drummer Scott Raynor), lyrical pining for a cool, independent (imaginary) girlfriend. References to their favorite Mexican food joint (Sombrero) and their pop-punk friends Unwritten Law capture ’98 San Diego as more than just the year the Padres got swept by the Yankees in the World Series. -- CHRIS PAYNE

87. Beenie Man, "Who Am I" (No. 40, Hot 100)

Beenie Man previously earned respect in his native Jamaica thanks to a role in 1997’s Dancehall Queen and party-starter singles like “Wickedest Slam” and “Romie.” But “Who Am I” brought his exaggerated “Woieee nah nah!” wails to the rest of the world. The track is one of dancehall’s few pop-culture masterpieces, with Beenie Man cheekily referencing both Luther Vandross’ 1981 jam “Never Too Much” and Missy Elliott’s "The Rain (Supa Dupa Fly)" over a ground-shaking low-end. “Who Am I” was adored so much that Beenie Man later transformed it into his 2000 track "Girls Dem Sugar," a sensual duet featuring Mya and production from The Neptunes that further established the original's immortality. -- BIANCA GRACIE

86. Alanis Morissette, "Uninvited" (No. 4, Radio Songs)

Alanis' 1995 debut Jagged Little Pill is the Canadian rocker's undisputed opus, but the harrowing City of Angels soundtrack single “Uninvited” built on that album's intensity, momentum, and overwhelming acclaim. The song scored her Grammys in the best rock song and best female rock vocal performance categories, and it made for a standalone smash that held fans over until Supposed Former Infatuation Junkie's arrival later that year. This was reflected on the charts, too: “Uninvited” topped the Adult Mainstream Chart, her third single to do so after "Ironic" and “Head Over Feet.” -- HILARY HUGHES

85. Monica, "The First Night" (No. 1, Hot 100)

As soon as producer Jermaine Dupri brilliantly built Monica’s “The First Night” around Diana Ross’ 1976 disco classic “Love Hangover,” we all knew this was going to be a surefire success. R&B artists typically sung about abstinence through emotional ballads (see Janet Jackson’s "Let's Wait Awhile”). But Monica played it ultra-cool about not giving it up so easy atop a thumping bassline. Her sassiness and self-worth on “The First Night” earned her a Hot 100 No. 1 smash and became an inspiration for future female singers to stand up to pesky men for years to come. -- B.G.

84. A Tribe Called Quest, "Find a Way" (No. 71, Hot 100)

With a new generation of New York rappers rising to prominence, A Tribe Called Quest were a fairly alien presence on '98 radio, particularly with "Find a Way," arguably their most inscrutable single to date. The Love Movement single was a curious, Dilla-helmed hypno-banger with an emotionally confused love-and/or-lust lyric and a strangely overstuffed chorus -- albeit one still catchy enough that the group held a bouncing-ball singalong to it in the song's video. "Find a Way" hardly scorched the charts, but it remains seared into the memory of everyone who experienced it, a song as mysterious and enchanting as the complex feelings it attempted to articulate. -- A.U.

83. Everclear, "Father of Mine" (No. 70, Hot 100)

Art Alexakis let it bleed. The Everclear singer-songwriter never shied away from dealing with his addiction on hits like “Heroin Girl,” and this swinging single from his band’s second major-label album hit hard, but with a velvet glove. With the band’s signature bouncy bubblegrunge sound, Alexakis laid bare residual anger and resentment about his dad splitting when he was a ten-year-old “scared white boy in a black neighborhood.” The last cut was the deepest, though: “Daddy gave me a name/ Then he walked away.” -- GIL KAUFMAN

82. Wyclef Jean, "Gone Till November" (No. 7, Hot 100)

As each member of the rap trio Fugees made their first solo statements following the group's '96 blockbuster The Score, Wyclef Jean dedicated his '97 debut The Carnival to showcasing his versatility as a rapper, singer, and musician. On the '98 single and standout track “Gone Till November,” the Haitian transplant makes his most striking divergence, with an orchestral ballad that acts as a vicarious comfort for every hustler’s lonely loved ones. Lyrically, it’s full of heart-wrenching twists, but it adds a sweetness to the Fugees’ raw candor that that could soothe any long-distance woes. -- BRYAN KRESS?

81. Edwin McCain, "I'll Be" (No. 5, Hot 100)

Long before Ed Sheeran delivered a spiritual successor with his chart-toppin “Perfect,” Edwin McCain crafted one of the most swoon-worthy, first-dance-ready love songs of the ‘90s with “I’ll Be.” The dynamic chorus is essentially a set of wedding vows in itself (“I'll be better when I'm older/ I'll be the greatest fan of your life”), and the way McCain passionately relays all of those heartfelt words – on top of a jazzy sax, no less – makes his declaration of love fitting for a belting sing-along and a wedding dancefloor, whether it’s 1998, 2018, or 2088. -- T.W.

80. Air, "Sexy Boy" (No. 22, Dance Single Sales)

The lead single and one of the standout tracks from Air’s enduring debut album, Moon Safari, “Sexy Boy” finds the French electronic duo at the peak of their crossover powers. Earning syncs with the 1999 film 10 Things I Hate About You and British TV series Queer as Folk, the dreamy-but-expansive downtempo number hit No. 22 on Billboard’s U.S. Dance/Electronic Singles Sales chart and helped launch the critically-acclaimed outfit to international prominence. -- MATT MEDVED

79. Tamia, "So Into You" (No. 30, Hot 100)

After being introduced via a pair of hit ballads, Tamia went left and took on a Commodores sample for her third single. Of all its enticing elements, the hook stands supreme, with a buttery vocal that matches the beat of the drum pattern just before Tamia glides off into a honeyed high note. The chorus was so delectable that Fabolous snatched it for the core of his own hit “Into You,” a No. 4 success on the Hot 100 in 2003, and it was a notable highlight of Childish Gambino’s BBC Live 1 Lounge set in 2015. -- TREVOR ANDERSON

78. Sheryl Crow, "My Favorite Mistake" (No. 20, Hot 100)

On her star-making 1993 debut Tuesday Night Music Club, Sheryl Crow established herself as a guitar-chugging rocker who could run laps around the male coterie of musicians in her circle. It was then that she showed a flair for fitting blues licks and power chords into a pop songwriting template, something she refined for her eponymous 1996 follow-up and even more so with 1998 chaser The Globe Sessions. In a way, “My Favorite Mistake” is where that skill set peaked: Her toffee vocals against the thrust and twang of six-strings and organs cement her as a true pop star in rocker’s clothing. -- STEVEN J. HOROWITZ

77. Cake, "Never There" (No. 78, Hot 100)

Though 1996's “The Distance” was Cake's breakout hit, “Never There” has managed to surpass it -- not only on the charts, but also in terms of its pop-culture endurance, thanks to its all-too-real lyrics. Loving someone who is, simply put, never there for you -- leaving you listening to an empty dial tone in their wake -- is a tale as old as time, and one that Cake successfully tapped into, pressing our emotions like buttons on a landline. -- LYNDSEY HAVENS

76. Will Smith, "Miami" (No. 17, Hot 100)

Big Willie Style was the solo debut album for Will Smith, but with five albums under his belt as the Fresh Prince and three massive blockbuster film credits (Bad Boys, Independence Day, Men In Black), he was hardly a fresh face when it dropped in '97. Which is largely why "Miami" managed to dominate 1998, despite being released as the album's fifth single. Of course, it helps that the song is an irresistible funk bop with some of the most iconic come-hither backup vocals of all time: "Welcome to Miami / Bienvenidos a Miami" will never not sound sexy. -- JOE LYNCH

75. Moby, "Honey" (No. 49, Dance Single Sales)

While Moby’s timeless Play LP is perhaps better known for producing international smashes like “Porcelain” and “Natural Blues,” the album’s opener and lead single, “Honey,” shouldn’t be slept on. Featuring bluesy looped vocal samples from U.S. folk singer Bessie Jones’ “Sometimes” over a driving piano and slide guitar, the track briefly graced Billboard’s U.S. Dance/Electronic Singles Sales chart while kicking off the best-selling electronic album of all-time in unforgettable fashion. -- M.M.

74. Seo Taiji, "Take Five" (Did not chart)

Seo Taiji remains South Korea’s “Culture President” for a reason -- he pioneered the industry’s embrace of diverse genres. “Take Five” marked another sonic transformation, one that eschewed the rap-rock of his prior group Seo Taiji and Boys. While his self-titled album was coated in the heavy metal of his early days, this track takes on a sunnier disposition with flahses of late-’90s college rock. After all, “Take Five” was a message to fans that he’d return to music after retiring in 1996. -- CAITLIN KELLEY

73. Boards of Canada, "ROYGBIV" (Did not chart)

"ROYGBIV" would be a pretty appropriate title for just about any Boards of Canada song -- their brand of effervescent downtempo is both so polychromatic and so naturalistic that a rainbow never seems more than a few measures away from poking out of its atmosphere. But this two-and-a-half minute instrumental is prismatic even by their standards: simple, stunning, organized with impossible geometric precision -- and, like all such ephemeral phenomenons, vanishing long before you're ready to say goodbye. --  A.U.

72. Usher, "My Way" (No. 2, Hot 100)

Usher’s first My Way single, “You Make Me Wanna...,” introduced him as a coy R&B star, while his second, “Nice & Slow,” replaced the coy with straight-up coital. But it was his third, “My Way,” that turned him into a freaky philanderer, the original Mr. Steal Your Girl: “She likes it my way,” Usher croons over a thrusting beat and interjections from Jermaine Dupri, one of the album’s co-producers, matching his boastful attitude with a bounce that stands the test of time. What perhaps ages less well is the music video, where Usher, dressed like a funhouse version of Alex from A Clockwork Orange, squares off against Tyrese in a junkyard. With a bounce house. Sure. -- C.W.

71. Janet Jackson, "Go Deep" (No. 28, Radio Songs)

Not only is this song tailor-made to get a party started, it's also its very own party contained in a song, from the crowd murmurs over the beat at the beginning to the group sing-along of a chorus. That super-loose vibe -- with its irresistible snare intro and cheeky sound effects sprinkled throughout -- is what makes it so danceable, and it perfectly matches the music video's foamy house party, so rudely interrupted by a pre-SNL Bill Hader as a pizza delivery boy at the end. -- KATIE ATKINSON

70. Missy Elliott feat. Lil' Kim & Mocha, "Hit 'Em Wit da Hee" (Remix) (No. 61, R&B/Hip-Hop Airplay)

This remix from the Can’t Hardly Wait soundtrack took some of the bite out of the original’s menacingly funky instrumental, but it compensated for that with new attitude-filled verses from Elliott, a moody, Björk-sampling coda from Timbaland, and, why not, a few random horse neighs for good measure. One thing that stayed the same? A feisty kick-off from Lil Kim that remains one of her best guest spots, thanks to its kooky pop-culture references (Finnegan’s Wake! Sarafina!) and zero-fucks tongue-twisters like “Christians repent then sin again/ Girls wanna be my friend again.” -- NOLAN FEENEY

69. Elvis Crespo, "Suavemente" (No. 84, Hot 100)

“Suavemeeeente!” The nasal cry from an unknown Puerto Rican merengue singer was ear-piercing and unforgettable. Elvis Crespo’s hyper-kinetic merengue, punctuated by shouts of “pequena" (little one) and “Que es la cosa!” topped Billboard’s Hot Latin Songs chart and even crossed over to the Hot 100. More impressively, Suavemente, Crespo’s debut solo album, sold nearly 1 million copies in the U.S. alone, according to Nielsen Music -- unheard of for a Spanish-language album, much less a merengue album. Remixed multiple times, the evergreen party track has been played from the streets of Egypt and massive concerts in Australia to the moon. Literally: “Suavemente” was the only Spanish-language song chosen by astronauts to include in the 2006 Discovery mission. -- L.C.

68. Brian McKnight, "Anytime" (No. 6, Radio Songs)

It's hard to talk about Brian McKnight's "Anytime" without getting cranky about how there's nothing like it today: There's a delicate stillness to the nocturnal ballad that feels almost antithetical to the streaming era, let alone contemporary radio. No grandstanding as McKnight lets out his soft chorus cry -- "Do I ever cross your mind... anytime?" -- more quiet than storm, as a Bruce Hornsby-like piano loop winds around him. Only on the bridge does he unleash, revealing the nights of crying himself to sleep, praying you'll come back to him, COME BACK TO HIM -- but that quickly gives way, ultimately leaving only the hook's devastatingly simple final sentiment: "I miss you." -- A.U.

67. Sarah McLachlan, "Angel" (No. 4, Hot 100)

Despite its use in countless TV specials, films, and infomercials, we shouldn’t lose sight of the song’s hauntingly real origin: McLachlan wrote the tune in response to the heroin overdose death of a Smashing Pumpkins’ touring keyboardist Jonathan Melvoin and the rising tide of musicians who turned to the drug to ease the pressures of the industry (“Fly away from here/ fFom this dark, cold hotel room”). Its specificity adds power to its poignancy, preventing the song from devolving into a centerless everyman ballad that overcompensates with excessive theatrics. -- T.A.

66. Elliott Smith, "Waltz No. 2" (Did not chart)

Unlike Smith’s previous hushed, downtempo singles, “Waltz” -- the first single off his fourth album, XO -- dives into a lusher, fuller sound for the singer-songwriter. The jangly production and Smith’s quivering vocals result in a well-crafted, and arguably more accessible, track from the intensely intimate indie-rock icon. And no matter how much time passes, the line “I'm never gonna know you now/ But I'm gonna love you anyhow” will always hit home. -- L.H.

65. K-Ci & JoJo, "All My Life" (No. 1, Hot 100)

Usually when a guy says your love reminds him of his mother, father, brother, and sister, that’s your cue to you sneak away to the bathroom and call an emergency escape Uber. But this duo wasn’t kidding when they said one lucky woman was their everything -- and they sold it, too, with a big yearning chorus that proved K-Ci and JoJo were more than just one half of Jodeci killing time during a hiatus. The sentiment may have been cheesy, but the top-notch songcraft on display here had no expiration date -- no wonder flashes of “All My Life” keep showing up in today’s hits. -- N.F.

64. Rammstein, "Du Hast" (No. 20, Mainstream Rock)

Every year has its breakthrough hit from a German industrial-metal band, and 1998 was no different. Wait, what? Yeah, for some reason, '98 saw a metal sextet from Berlin bust onto TRL and the American charts with a chugging industrial track tinged with flourishes of '90s house and campy operetta. The wordplay -- auf Deutsch, "duhast mich" (you have me) and "du hasst mich" (you hate much) sound the same – was lost on most U.S. listeners, but a guitar riff this meaty transcends any language. -- J.L.

63. Whitney Houston & Mariah Carey, "When You Believe" (No. 15, Hot 100)

What do you get when the two biggest powerhouse divas of the ’90s combine forces for a major motion picture soundtrack? Apparently a fairly traditional, saccharine power ballad. No shade, though: Whitney and Mimi sound excellent trading verses, and their harmonies are unclockable. The song only managed to peak at No. 15 on the Hot 100, but the pair got the last laugh: this Prince of Egypt cut took home the Academy Award for best original song. -- P.C.

62. All Saints, "Never Ever" (No. 4, Hot 100)

Spice Girls notwithstanding, a whole host of U.K. girl groups flew under the American radar in the late '90s -- but this All Saints gem managed to carve out a space on U.S. radio, thanks to its catchy chorus and oh-so-earnest spoken-word intro. The lyrics can be a little clunky in places (we're looking at you, "shower"/"scour" rhyme sequence), but they also did the public service of introducing stateside audiences to the proper British pronunciation of "Z." -- K.A.

61. Goo Goo Dolls, "Slide" (No. 8, Hot 100)

Its soundtrack-derived predecessor was a four-quadrant smash that made the band household names, but "Slide" proved that Buffalo's finest were still peerless craftsmen when it came to finding the sweet spot between adult rock and adult contemporary. "Put your arms around me/ What you feel is what you are, and what you are is beautiful" belts frontman Johnny Rzeznik with all the urgency and un-self-conscious sentimentality of the fraught young relationship described in the verses. It was obvious that the Goo Goo Dolls hadn't come this far to end up being mistaken for one-hit wonders. -- A.U.

60. N.O.R.E., "SuperThug (What What)" (No. 36, Hot 100)

That helicopter whirring you hear at the beginning is the sound of the artist who would shape pop music at the turn of the millennium touching down on 1998. No, not the rapper formerly known as Noreaga -- though he has more classic singles than you may realize, starting with this one -- but rather production duo The Neptunes, whose knocking, blistering beat to "SuperThug" mixed old-school hardness with electro-funk futurism and New Jack Swing hooks (and even a Puffy-style "Heart of Glass" lift, why not) for one of the most potent hip-hop singles of the late decade. There'd end up being plenty more where that came from, thank God. -- A.U.

59. Radiohead, "No Surprises" (Did not chart)

Before Radiohead became pioneers in dystopian electronic music, they were creating melancholic, visionary rock that could soundtrack any mental breakdown. Pairing grievances that paint the mundane as fatalism (“a job that slowly kills you”) with the visual of Thom Yorke’s unfazed visage getting flooded in a water tank, the existential dread of “No Surprises” begins to seep through the pleasant, illusory guitar melody. Then the “final fit” provides the kind of relief that only comes from breaking the surface, without a moment to spare. -- B.K.

58. Massive Attack, "Teardrop" (Did not chart) 

Though its legacy in America began when it was selected as the theme song to House, "Teardrop" was Massive Attack's first -- and, to date, only -- top 10 hit in the U.K. six years prior. That it possesses the trip-hop trio's most accessible hook very much helped this, but it's all in the other details, too -- vocalist Liz Fraser's delicate and emotive performance, the stormy piano strokes, its haunting, habitual harpsichord riff. It's atmospheric dejection perfected; no wonder music supervisors still can't get enough of it. -- K.R.

57. Faith Hill, "This Kiss" (No. 7, Hot 100)

For anyone who has ever fallen in love, “This Kiss” sublimely evokes the joyous, out-of-body experience that comes from kissing a special someone. Hill’s silky lilt perfectly embodies the universal emotion that most people can’t put into words, making it easy for everyone to belt out the infectious refrain as if it were just for them. Still a radio singalong, the song helped pave Hill’s path to country icon status -- and sealed her first top 10 hit on the Hot 100 and AC charts. -- GAIL MITCHELL

56. Barenaked Ladies, "One Week" (No. 1, Hot 100)

"One Week" is, perhaps to its credit, the type of song that almost could not have emerged in any other era of American pop music: A catchy, guitar-driven confessional with a tongue-in-cheek tag line and a collection of verses that owe more to rap than to conventional rock, it’s a quintessential snapshot of the melting pot that was late-'90s mainstream music. And to give it the '90s coup de grace, it was covered by Weird Al in a parody that was probably even better than the original. -- DAN RYS

55. Garbage, "I Think I'm Paranoid" (No. 6, Alternative Songs)

Garbage debuted “I Think I'm Paranoid” -- the second single from the band's platinum-certified sophomore album Version 2.0 -- live at a gig in Wisconsin on May 15, 1998, while kicking off the record’s tour. By September, it was sitting in the top 10 on the U.S. Alternative Songs chart, thanks to some kickass electric bass, an inspired '60s pop interpolation, and Shirley Manson's cleverly distorted vocals. The jam also appeared in the first game of the Rock Band video game series, making it the first introduction to Garbage for many millennials. -- GAB GINSBERG

54. Backstreet Boys, "As Long As You Love Me" (No. 4, Radio Songs)

Though the Backstreet Boys had seen international success prior to 1998 with breakout hit “Quit Playing Games With My Heart,” they hadn’t really shown their sweetly sentimental side with a single. Then came “As Long As You Love Me,” which proved that they can be plenty sappy without losing sight of their punchy pop sound. It was also a fine showcase of their harmonizing abilities, which helped BSB establish that they were -- and still are -- more than just a group of five heartthrobs with catchy songs. -- T.W.

53. Eve 6, "Inside Out" (No. 28, Hot 100)

This track is a slice of the inoffensive, radio-ready rock that dominated the ’90s -- from Spin Doctors' “Two Princes” early in the decade to “Hey Leonardo” by Blessid Union of Souls towards the end. At the genre’s pinnacle were immediately catchy hooks that dared you to sing along, even if they stuffed a dictionary’s worth of words into them. And with words like “oblivion” and “rendezvous” haphazardly crammed into this track’s nonsensical hook, this song would prove challenging for even the most skilled karaoke all-star -- though they can't resist trying anyway. -- P.C.

52. Lord Tariq & Peter Gunz, "Deja Vu (Uptown Baby)" (No. 9, Hot 100)

According to the accountants, in 1998, Donald Fagen -- white, 50 years old at the time, eternally cranky and given to jazz snobbery -- wrote the lyric “cuz I’m quick to slide off and slide this dick up in your wife.” The Bronx’s Peter Gunz nimbly delivers the line on the triumphant “Deja Vu (Uptown Baby),” an ode to the birthplace of hip-hop, but check the liner notes and you’ll find that the only credited writers are Steely Dan’s Fagen (of Passaic, New Jersey) and Walter Becker (Queens). Gunz described the unorthodox publishing arrangement as “a stick up” in a 2015 interview. Twenty years later, the fat bass line and guitar lick, nicked from Aja opener “Black Cow,” still ring off as a reminder of how rap music transforms the past into the present, and just how dirty the game can be. Like KRS-One said, “Bronx keeps creatin’ it and Queens keeps on fakin’ it.” -- R.S.

51. Lenny Kravitz, "Fly Away" (No. 12, Hot 100)

Lenny Kravitz had broken out as a modern-rock mainstay with 1993’s “Are You Gonna Go My Way,” but following that, he was largely absent from the conversation -- until the fourth single of 1998’s 5, which introduced the world to the unavoidable crossover smash “Fly Away." A simple, guitar-heavy track with an electric hook about wanting to escape -- be it New York City, the world, or the news -- the track earned him his second top 10 radio hit and scored him his first Grammy win for best male rock vocal performance, a category he'd win again in 1999 and 2000. -- XANDER ZELLNER

50. Third Eye Blind, "Jumper" (No. 5, Hot 100)

In an era when agony was still Billboard Hot 100 ecstasy, 3EB’s Stephan Jenkins was the king of pain. How else do you explain this creamy slice of acoustic power-pop with a killer wah-wah guitar solo and surprisingly empathetic lyrics about desperation, which continue to resonate today? It’s been called the band’s “suicide song,” but really it’s a longing prayer for connection, hope, and second chances. If teen angst ever needed a title track, this is it. -- G.K.

49. Uhm Jung Hwa, "Invitation" (Did not chart)

Alluring in its breathy vocal delivery and sleek synths, Uhm’s tantalizing 1998 hit was written by J.Y. Park, who brought his distinct smooth grooves to this classic. With a sense of dreamy sensuality and angsty raps from g.o.d’s Joon Park and and Danny Ahn, “Invitation” is still one of the most memorable Korean songs from the ‘90s, and Uhm still regularly performs it. -- T.H.

48. The LOX feat. Lil Kim & DMX, "Money, Power & Respect" (No. 17, Hot 100)

In 1998, New York rap was dripping with grit and grime. Dark hoodies, Timberlands, and FUBU jerseys were the essential uniforms in the city of Gotham. While JAY-Z and DMX set the pace with their hard-nosed efforts, The LOX found a place in Big Apple immortality with their timeless single "Money, Power & Respect." Without hesitation, Yonkers' triumvirate takes aim at rap charlatans with their grizzly deliveries, while fourth-verse guest DMX pulverizes the hard-hitting East Coast beat and co-starring diva Lil' Kim pounces on the hook to deliver the essential "key to life." Twenty years later, "Money, Power & Respect" remains the unwritten law everyone abides by in hip-hop. -- CARL LAMARRE

47. Marilyn Manson, "The Dope Show" (No. 15, Alternative Songs)

Marilyn Manson went pop! Kind of! When "The Dope Show" was released, it was tough to tell what was more shocking: Manson’s glam-rock stomp or the androgynous Hollywood alien look that he sported in the video. The song was way more electronic and slinky than some of Manson’s other music to that point, but it still had the dark, intrinsically rock power chords of something like “The Beautiful People” from 1996’s Antichrist Superstar, as well as the societal criticism. The song was undoubtedly more melodic and user-friendly, but really, we should’ve seen it coming: The lord of darkness did cover “Sweet Dreams (Are Made of This)” and (eventually) “Tainted Love,” after all. -- C.W.

46. Deborah Cox, "Nobody's Supposed to Be Here" (No. 2, Hot 100)

In the era of Mary J., Mariah, and Whitney, it was tough for most big ballads to break through the airwaves, making the record-breaking run of "Nobody's Supposed to Be Here" on the R&B charts all the more impressive. The song, co-written by Montell Jordan, shattered the then-record for the longest stay atop Hot R&B/Hip-Hop Songs, with 14 weeks in command. It’s easy to see why: A textbook example of R&B-gospel fusion, “Nobody’s” melts a heartbroken protagonist’s steely resolve as she finds love again and wraps it in a lung-busting display of melisma, climaxing in an extended high note that has humiliated reality competition hopefuls for decades. -- T.A.

45. Neutral Milk Hotel, "Holland 1945" (Did not chart)

On its surface, “Holland, 1945” fits comfortably with the fuzz rock of the post-grunge indie era, but digging deeper into reclusive frontman Jeff Mangum’s lyrics reveals a uniquely sincere ode to Holocaust victim Anne Frank that serves as the crux of the band’s the seminal album In The Aeroplane Over The Sea. Far beyond the shout-outs the group would receive on NBC primetime, the band’s work remains relevant as an early model for bookish indie rock that distorts the past and present to create a world that could only belong to a singular, unrestrained imagination. -- B.K.

44. Ricky Martin, "The Cup of Life" (No. 45, Hot 100)

Ricky Martin burst onto mainstream consciousness in 1999 with a performance “The Cup of Life” at that year's Grammy Awards, prompting host Rosie O’Donnell to coo: “I never knew of him before tonight, but I’m enjoying him soooooo much.” And so was everyone else: “The Cup” never reached the upper echelons of the Hot 100 (it hit No. 60 in 1998, reentered in 1999, and peaked at No. 45 in August), but it jump-started the original “Latin Explosion” in English-language pop, which would eventually bring us Shakira, Marc Anthony, J-Lo, and Enrique Iglesias, making 1998 a seminal year for Latin music. To date, it remains the most emblematic and best-known World Cup anthem in modern history, and it's the song that set in motion the serious competition to vie for a World Cup song. And really, is there really anyone in the world who hasn’t shouted “Un, dos, tres/ Allez, allez, allez” at a party? -- L.C.

43. Faith Evans, "Love Like This" (No. 7, Hot 100)

As soon as you hear the mesmerizing opening beats, you can’t help but rock to what’s since become a party, club, and skating-rink mainstay. If fact, the latter doubles as the backdrop for the song’s video, with skaters undulating to its mellow groove and Evans’ hot-buttered vocals. An arresting portent of the R&B and hip-hop fusion that was about to take over Top 40, Evans’ Grammy-nominated smash undoubtedly celebrates the singer’s romance with late husband and rap icon Notorious B.I.G., who died the year before its release. -- G.M.

42. D'Angelo, "Devil's Pie" (No. 69, Hip-Hop/R&B Airplay)

Loose and low-key, with doubled vocals that still come off as almost breathy at times, the track is nonetheless pointed and straightforward in its themes. Some have called it an attack on materialism; others say it's an indictment of capitalism. D’Angelo himself, speaking on the feel of the song, compared it to the chants of a chain gang or slaves in a field. With its biblical and apocalyptic themes, it can just as easily be seen as an astute observation of the many trials that people put themselves through for perceived benefits, even when those just feed right back into the same cycle of repression all over again. And D’Angelo manages to pack that all in without most people even really hearing the words, instead just losing themselves in the improvisational undertow. -- D.R.

41. Master P feat. Fiend, Silkk the Shocker, Mia X & Mystikal, "Make 'Em Say Uhh!" (No. 16, Hot 100)

It takes a village -- or, at the very least, a formidable starting five -- to turn a local label into a national and eventually global phenomenon, but Master P and his soldiers took No Limit from a New Orleans institution to the Bad Boy of the South with "Make "Em Say Uhh." The breakthrough hit featured all the label's heavy hitters at the top of their game, though they're really laying down track for the song's bleating horns and brain-melting singalong chorus, as undeniable as Karl Malone coming down the lane on the fast break. Even 15 years after No Limit first folded, you still best clear the way when you hear the tank creepin'. -- A.U.

40. Shania Twain, "You're Still the One" (No. 2, Hot 100)

By the start of 1998, Shania Twain was clearly a major country success: She had five Hot Country Songs No. 1s, with a few of those crossing over onto the Billboard Hot 100. But “You’re Still the One” represented a whole new kind of success for Twain, as the heartfelt ballad went all the way to No. 2 on the Hot 100, proving that she wasn’t just a country star -- she was an all-around superstar. While the Ontario native has had plenty of hits since, nothing gives listeners the feels quite like Twain’s breathy vocals on the piano-tinged verses or the powerful build-up to the song’s chorus. And for those lovers who had this song soundtrack their wedding in 1998, Twain is likely still the one they run to for that musical romance 20 years later. -- T.W.

39. Usher, "Nice & Slow" (No. 1, Hot 100)

Shout-out to Jermaine Dupri and the Casey twins of Jagged Edge for helping craft one of freakiest R&B slow jams of all time. Usher’s “Nice & Slow” is surely responsible for the creation of half a generation, including some of you who may be reading this right now. The ballad oozes sex appeal, with a young Usher (who had recently graduated from teendom) spelling out of exactly how he plans to make love to his lady -- as well as, uh, his entire name: “They call me U-S, H-E-R, R-A, Y-M, O-N-D / Now, baby, tell me what you wanna do with me?” Despite being only 20 years old at the time, the singer channeled the confidence of many R&B greats before him, as his tender vocals caressed the song’s languid production. “Nice & Slow” became Usher’s first Hot 100 No. 1, and if you scroll through your #MCM’s phone right now, you'll probably still find this on his “let’s get it on” playlist. -- B.G.

38. The Offspring, "Pretty Fly (For a White Guy)" (No. 53, Hot 100)

Following the willful artifice of the '80s, there was precious little worse in the '90s than being labeled a poser. The Offspring eviscerated dim-witted wannabees with their ubiquitous rock-radio hit "Pretty Fly (For a White Guy)," an O.C. punk anthem that sampled Def Leppard, referenced talk show maven Ricki Lake, and sent up the kids who claimed to love hip-hop but jammed to Vanilla Ice instead of Ice Cube. Few songs are so sonically of their era as this one, but the delivery -- which is more smirk than fury -- ensures that it's sorta timeless. -- J.L.

37. Aerosmith, "I Don't Want to Miss a Thing" (No. 1, Hot 100)

Aerosmith's catalog is peppered with classic-rock perennials, but they didn't score their first Hot 100 No. 1 until "I Don't Wanna Miss A Thing" had them holding the top spot on the chart for four straight weeks. They performed the Diane Warren-penned single for the soundtrack for Armageddon, the apocalyptic blockbuster starring Steven Tyler's daughter, Liv. The platinum-certified family affair delivered one of Tyler's most impressive vocal performances and the stuff of slow-dance dreams for school dances everywhere that fall, and in 1999 it'd earn an MTV Moonman, a Grammy nomination, and even Aerosmith's first Oscar nod. -- H.H.

36. Fastball, "The Way" (No. 5, Radio Songs)

In the grand tradition of radio smashes that sound much happier than they should, "The Way" was inspired by the tragic story of an elderly couple on an aimless interstate road trip that ended with their car plummeting off a cliff. The true trick of this deceptive song is getting you to hum along at first, and then to sing the storytelling lyrics, and then to actually process what you're singing as the jangly guitars strum behind you: "They just drove off and left it all behind 'em/ But where were they going without ever knowing the way?" -- K.A.

35. JAY-Z feat. Amil & Ja Rule, "Can I Get A..." (No. 19, Hot 100)

Two years removed from releasing his debut opus, Reasonable Doubt, JAY-Z kept his momentum up with his 1998 project Vol. 2...Hard Knock Life. Firmly on his way to being a bona fide rap titan, Jay recruited two young and hungry MCs for "Can I Get A...," and while JAY-Z's sleek 16 won the approval of the clubs, it was Amil's swaggering verse and Ja Rule's rugged style that stole the show. Even to this day, men and women both chirp the song's infectious hook at every summer brunch and after-hour spot. Grab a drink and bounce with Jigga. -- C.L.

34. KoRn, "Got the Life" (No. 15, Mainstream Rock)

The song that proved nu-metal was a musical force powerful enough to compete with anything coming out of Orlando in the late '90s, "Got the Life" was an absolute juggernaut: a ripping scythe of a guitar riff laid over a bass groove that chugged like a hellish choo-choo, tied together with a vocal of a lifetime from frontman Jonathan Davis. He howls, he whimpers, he scats as he questions God and gets rightfully put in his place: "God pains me, the more I see the life, who wants to see?/ God told me, I've already got the life." Carson Daly would understand soon enough. -- A.U.

33. Next, "Too Close" (No. 1, Hot 100)

This sexy nod to what can naturally arise when two bodies come in close proximity combines a melodic mid-tempo track with a sly, mischievous hook that left a lot of listeners unsure of the relatively explicit content they were singing along to: “Baby, when we’re grindin’, I get so excited/ Ooh how I like it, I try but I can’t fight it/ Oh you’re dancin’ real close … / You’re making it hard for me.” Propelled by suave harmonies, the R&B trio rode all the way to platinum certification -- and the No. 1 spot on the Hot 100 and R&B charts. -- G.M.

32. Spice Girls, "Stop" (No. 16, Hot 100)

The thing often lost about the Spice Girls is that they weren’t afraid to wallow in kitsch. By the time they’d reached international acclaim with 1996’s Spice, they had traipsed from hip-hop-inspired girl power anthems (“Wannabe”) to shiny pop bangers with harmonica solos (“Say You’ll Be There”). They were known for taking chances, no matter how much bubble and gloss they wrapped their songs in, and “Stop” took no exception. From 1997’s Spiceworld (which accompanied the delightfully absurd film, a deserved cult classic), “Stop” was all pomp and circumstance and bleating horns, the precise type of song to soundtrack a movie montage. -- S.J.H.

31. Madonna, "Frozen" (No. 2, Hot 100)

The lead single from Madonna’s seventh album, Ray of Light, “Frozen” is a masterpiece of William Orbit-produced electro-pop that has arguably aged better than any of her hits since. The track was released just a few months before Madonna’s 40th birthday -- and less than a year and a half after she’d become a mother for the first time --  and both the spare lyrics (about a cold-hearted lover) and the cool, lush, and enveloping interplay of synthesizers, strings, and Eastern percussion showcase a wiser, more mature Madonna, one still at the top of her game. “If I could melt your heart,” she sings in the chorus. With “Frozen,” she does. -- FRANK DIGIACOMO

30. Eagle-Eye Cherry, "Save Tonight" (No. 5, Hot 100)

The son of jazz trumpeter and Ornette Coleman collaborator Don Cherry, Eagle-Eye Lanoo Cherry’s debut single arrived firmly in the pop lane, courting Top 40 radio with driving acoustics and an insistent chorus. His debut set, Desireless, and three subsequent full lengths produced nothing to save Eagle-Eye from one-hit wonder status, but his teary-eyed one-night stand sing-along was such a massive hit (it peaked at No. 5 on the Hot 100) that it won’t be leaving '90s Night any time soon. -- C.P.

29. Dixie Chicks, "Wide Open Spaces" (No. 41, Hot 100)

The title track from the band's fourth album, but the first with lead vocalist Natalie Maines, features the best of what the Dixie Chicks have to offer: beautiful harmonies, an angsty-but-hopeful storyline, and a twangy violin break. With this breakthrough hit -- leading a blockbuster album that would eventually be certified diamond -- the Chicks proved there is plenty of open space for women in country. -- D.W.

28. Stardust, "Music Sounds Better With You" (No. 62, Hot 100)

This 1998 dance-club gem is often (and understandably) mistaken for a Daft Punk song. While the French robots did employ Stardust’s sole single as their iconic Alive 2007 tour encore, the release actually only features one-half of the duo, Thomas Bangalter, in partnership with Alan Braxe and Benjamin Diamond. A reliable floor-filler that topped Billboard’s Dance Club Songs chart and even cracked the Hot 100, “Music Sounds Better With You” boasts many of Daft Punk’s early stylistic hallmarks, including the filtered funk guitar licks that inspired a wave of copycat releases in its wake. Bangalter reportedly declined $3 million to produce a full Stardust album, leaving this infectious late-'90s anomaly one of dance music’s most beloved one-hit wonders. -- M.M.

27. Jennifer Paige, "Crush" (No. 3, Hot 100)

A year before newly minted pop stars like Britney Spears and Christina Aguilera dominated the scene with their bubblegum anthems, Jennifer Paige played a major role in driving the sound of what was to come for the genre in Y2K. And it was all thanks to her effortless debut single, “Crush.” The singer embodied true savagery with her “it’s not that serious” attitude and sweet, soulful vocals as she casually shut down a poor guy’s flirtatious efforts: “Don't make a fuss / And go crazy over you and me.” “Crush” became a transatlantic hit, and though Paige's sound has come a long way since “Crush” -- she released the electro-pop Starflower LP last spring -- it’s hard to shake off the unforgettable time she first sha-la-la-la’ed into our hearts. -- B.G.

26. Mariah Carey feat. Bone Thugs n Harmony, "Breakdown" (No. 53, Radio Songs)

The soul ballad that begins gently only to later explode and soar on the wings of heartbreak or desperate horniness, this is nothing novel. What makes “Breakdown” special is how perfectly the lyrics describe this arc, and that Mariah Carey sings it. She unfolds the tale: “You called yesterday to basically say/ That you care for me but you’re just not in love.” Damn. Knowing her angles, Mariah tells this man that, actually, she’s feeling the same way, even though it’s “pretending,” that “gradually [she’s] dying inside.”

While cramming as many words as possible into the chorus, she enunciates the particulars of her disguise. “Better get control,” Krayzie Bone and Wish Bone intone behind her topline, and could she have picked rappers who are more in control of their vocal peaks and valleys than two members of Bone Thugs? She lets the mask slip at 3:10, riffing and running up the scales behind the pristine chorus. “How do I feel? I’m losing my mind,” she wails. And if you don’t have chills at this point, what could you possibly know about life and loss and rhythm and blues? -- R.S.

25. Janet Jackson, "I Get Lonely" (No. 3, Hot 100)

Desperation isn’t supposed to sound sexy. It’s supposed to make you sound pathetic, needy, maybe a little unhinged. And it usually does -- unless you are Janet Jackson, singing about loneliness over a Jimmy Jam and Terry Lewis beat that snaps and glides and makes you move despite your fragile state. Such is “I Get Lonely,” the third single from The Velvet Rope, Jackson’s gorgeous album of intense introspection. “Lonely” clocks in at over five minutes, but it hits all the right spots: a full-voiced chorus of Jackson multiplied and plainly stating her feeling; and a handful of waiting-by-the-phone verses; a breakdown where she coos -- what else -- “gonna break it down, break it down, break it down.” Like any good song, this chorus provides that much-needed moment of release. Unlike any good song, this chorus happens six times, repeating the same insistent two lyrics per refrain. Twelve climaxes in fewer than half as many minutes? Only Janet gets it done like that. -- C.W.

24. Goo Goo Dolls, "Iris" (No. 9, Hot 100)

This eternal, shining hit from the City of Angels soundtrack is a blockbuster doe-eyed drama distilled into a five-minute rock ballad. Just as Rzeznik’s lyrics reflect the plight of Nicholas Cage’s lovelorn angel (“You’re the closest to heaven that I’ll ever be”), “Iris” mirrors the feature film its mass appeal would eventually transcend. Before being released as a commercial single, it it spent a whopping 18 weeks leading Billboard’s Radio Songs chart and another four atop the Mainstream Top 40; only a soon-canceled rule about singles requiring a physical release to count for the Hot 100 kept it from likely topping that chart too. 

Twenty years later, the magic still resonates: the way the acoustic guitar and mandolin intertwine, the way each bass note lingers, the tug-of-war between the guitars and strings in the bridge, the climax of that skyward electric solo. Ballads… they don’t make ‘em like this anymore. -- C.P.

23. DMX feat. Sheek, "Get at Me Dog" (No. 39, Hot 100)

"Where my dogs at?" Everywhere, soon enough: "Get at Me Dog" launched DMX to stardom and parent album It's Dark and Hell Is Hot to the top of the Billboard 200 -- the first of his four consecutive such chart-toppers. The song's bark was ferocious even before the rapper born Earl Simmons actually started yapping at chorus' end; few other breakthrough singles in history feel this focused, this determined, this nasty. Credit X, playing both the impending threat to the game and its Viper-like security system, as well as producer Dame Grease, who succinctly summed up the song's sea-change effect in a recent Hell Is Hot oral history: "I produced the last song of the shiny suit era with 'If You Think I’m Jiggy' with The LOX, and the first song of the bring-it-back-to-the-streets era with 'Get At Me Dog.'" -- A.U.

22. Marcy Playground, "Sex & Candy" (No. 8, Hot 100)

This New York band’s quirky downtempo hit set a record at the time with 15 weeks spent atop the Alternative Songs chart… and none of it made any sense. At all. The song was reportedly inspired by a comment about the post-coital smell in singer John Wozniak’s room, but two decades later the phrases “platform double-suede” and “disco lemonade” are still the alt-rock equivalent of “covfefe.” Though MP would never come within spitting distance of another hit this massive, “S&C” is a handy grave marker for the end of a period when the remnants of grunge’s dark underbelly and the about-to-explode teen-pop revolution lived in perfect harmony. -- G.K.

21. Will Smith, "Gettin' Jiggy Wit It" (No. 1, Hot 100)

A quintessential dad rap, “Gettin’ Jiggy With It” finds the Fresh Prince bragging about his dance moves over a zig-zagging Sister Sledge sample, pretending to smoke cigars (“it’s for the look”) and charming a woman who wears a “Prada bag with a lot a stuff in it!” It’s the G-rated brother to Smith’s sultry “Miami,” and a song you might laughingly roll your eyes at but can’t help dancing to. The MTV VMA-winning music video is just as entertaining, with Smith showing off an array of flashy '90s fashions around (where else?) Las Vegas. What does it mean to get jiggy, and what are we gettin’ jiggy with? Great news: It doesn’t matter. The fun-loving track spent three weeks atop the Hot 100 the spring of 1998 -- the same year Smith’s son Jaden was born. -- T.C.

20. Harvey Danger, "Flagpole Sitta" (No. 38, Radio Songs)

Seattle rock group Harvey Danger delivered one of the most memorable alt-rock radio hits of the decade with “Flagpole Sitta,” an ode to '90s hipsters and “raging against machines.” The song still rules two decades later because it truly embodies an era -- through a chorus of “bah bahs,” frontman Sean Nelson shakes his fist at television and the tech boom, espousing his preference to “publish ‘zines” or get a tongue piercing. With no shortage of irony, of course, the anti-anthem itself went mainstream, reaching No. 3 on the Alternative Songs chart and top 40 on Radio Songs. In a 2017 interview with Stereogum, Nelson explained that part of the reason the song has had such a successful shelf-life is because it’s so self-aware. “The thing that makes me most comfortable about the fact that ‘Flagpole Sitta’ has stuck around is that it is really conscious of the fact it is a piece of garbage," he explained, "in the same way that everything in pop culture is a piece of garbage." -- X.Z.

19. Big Punisher, "Still Not a Player" (No. 24, Hot 100)

Already ahead of the curve as hip-hop began pivoting toward mainstream pop, “Still Not A Player” -- by the late Bronx MC Big Punisher and R&B wingman Joe, a sequel to Pun's '97 hit "I'm Not a Player" -- was two decades ahead of current trends, where remixes immediately surpass the original and Top 40 hits seamlessly integrate Spanish with English in their lyrics. Whether it was a promise to stay faithful or just a parsing of words (“I’m not a player I just fuck a lot”), “Still Not A Player” was a sentiment that connected with enough listeners to propel Pun’s debut album, Capital Punishment, to No. 5 on the Billboard 200, later becoming the first Latin hip-hop album to go platinum. -- B.K.

18. Fatboy Slim, "The Rockefeller Skank" (No. 76, Hot 100)

Stretching out a Lord Finesse vocal like he's big beat's answer to Steve Reich, Fatboy Slim melded surf guitar, hip-hop, funk, and process music to create one of the most exhilarating dance achievements of the '90s. Endless appearances in TV shows and trailers have multiplied its pop-culture influence while diminishing its musical impact, but when it first emerged, there was practically no precedent for it in mainstream music -- hell, people were genuinely slapping their CD players and radios when that last vocal loop played seemingly ad infinitum at the end. -- J.L.

17. Pras feat. Mya & Ol' Dirty Bastard, "Ghetto Supastar (That Is What You Are)" (No. 15, Hot 100)

On paper, the idea of Ol’Dirty Bastard guesting on a song that repurposes the Dolly Parton and Kenny Rogers 1983 hit “Islands in the Stream” sounds like a Chappelle's Show skit, but incongruities are one of the things that made “Ghetto Supastar” the most deliriously irresistible song of the summer of '98. Featured on the Bulworth soundtrack -- which also implausibly depicted a then-68 year-old Warren Beatty rapping -- this hip-pop confection is a bacon-topped Krispy Kreme, alternating between Mya’s sweet lacquered vocals and the savory crunch of Pras Michel and ODB’s rhymes. The music is a dead-if-you-don’t-dance mix that sounds like Lalo Schifrin’s Mission: Impossible theme got busy with an unused bassline from Queen’s “Another Bites the Dust” sessions. And from the start, the song drops little sonic gifts that still resonate today: the gruff voice (ODB?) repeating Mya’s lines in the opening hook, the way Dirty strings out “in the hooooooood,” and that fuzzy guitar solo that closes the song. -- F.D.

16. New Radicals, "You Get What You Give" (No. 36, Hot 100)

There are endless reasons why "You Get What You Give" remains a great pop song. For starters, it's packed with clever lyrics -- including its popularization of the now-unavoidable portmanteau "frienemies" -- but the words aren't all in the name of wordplay. No, the real meat of the song is a series of uber-sincere platitudes meant to build up young music fans to confidently rage against the machine: "Don't let go, you've got the music in you … Don't give up, you've got a reason to live."

And in case you were distracted by the song-closing, name-dropping kiss-off to Courtney Love and Marilyn Manson, the song even spells out exactly who that "machine" is, including the health insurance industry, the FDA, and bankers. (In other words: We're still fighting the same fight 20 years later). And considering how much lyrical content is packed into four-plus minutes, the real wonder of it all is how infectious the song is. It all works thanks to Gregg Alexander, who -- despite his best attempts to hide from fame under the brim of his bucket hat, dissolving the Radicals after just one album -- remains a producer and songwriter, working that same magic behind the scenes on the last two decades of pop. -- K.A.

15. 2Pac, "Changes" (No. 32, Hot 100)

Released as a new single from his 1998 Greatest Hits set, "Changes" has since become a cultural touchstone, one that will forever remain relevant for acutely commenting on racial injustices from police brutality to packed penitentiaries -- issues that are arguably more prevalent today than ever. And in ‘98, a decade before Barack Obama would become president, 2Pac stated: “We ain't ready to see a black president,” as if foreshadowing what would follow Obama’s two-term run. But while Pac pleads for change over glistening, Bruce Hornsby-borrowed keys throughout the track, what will always hit hardest is the resignation that, then and even still decades later, “That's just the way it is.” -- L.H.

14. Celine Dion, "My Heart Will Go On" (No. 1, Hot 100)

Talent shows would never be the same again. In 1998, despite already having dropped vocal bombshells with “The Power of Love” and “All by Myself,” Queen Celine somehow topped herself with this literal Titanic single, which marries everything one loves (or hates) about Dion: Her breathy, emotive half-whisper and her half-hum singing, which builds, of course, to an erupting crescendo that makes even the resolute cynic think the world can be good again.

And it was certainly good to the James Horner- and Will Jennings-penned song: “Heart” debuted at No. 1 on the Hot 100 -- a first for Dion --  and earned an avalanche of accolades, including the Academy Award for best original song and Grammy prizes for record and song of the year. Beyond its contemporary success, appreciation for the song continues. How many singers do you know can dust off a 20-year-old song on a national award show to rousing reception? Wherever you are, don’t be surprised if Celine is called back to the stage for the 30th, 40th and 50th anniversaries. The song will go on and on. -- T.A.

13. Hole, "Celebrity Skin" (No. 85, Hot 100)

With three fierce power chords and a four-word, deliciously threatening challenge -- Oh, make me over -- Courtney Love shot Hole from alt-rock heroes to TRL contenders. Co-written by Billy Corgan, the title track and lead single from the band's third album served up a scathing condemnation of fame and bullshit beauty standards on an unmistakably grunge-y platter. Its deafening might, wry sarcasm, and scream-along chorus had listeners hooked, and the charts proved it: "Celebrity Skin" spent four weeks at No. 1 on the Alternative Songs chart, with its parent LP breaking into the top ten of the Billboard 200. -- H.H.

12. Beastie Boys, "Intergalactic" (No. 28, Hot 100)

Decades before EDM stars outfitted their bass drops with chopped-up, pitched-up vocals that sounded like wild animals, the Beastie Boys messed around with a vocoder and realized they didn’t need much -- two words, really -- to get listeners going buck-wild on the dancefloor. Once the beat kicks in, good luck extricating yourself from the trio’s riptide of goofy rhymes and one-liners, which even twenty years later will come back to you with the ease of schoolyard rhymes. And lest you think we’re overstating the irresistibility of Hello Nasty’s lead single, consider this: The song was a hit on Billboard's pop, rhythmic, alternative, and mainstream rock charts all at the same. In other words: Everyone was coming from Uranus to check their style.

11. Semisonic, "Closing Time" (No. 11, Radio Songs)

“You don’t have to go home, but you can’t stay here.” Imagine flipping a line that countless bartenders have said millions of times into the hook of your signature song: They call that “forever money.” That’s the magic of Semisonic leader Dan Wilson’s timeless homage to final call, which spent 25 weeks on the Adult Alternative Song charts, peaking at No. 4 in May 1998. It's way more than just a song custom-made to be bellowed by bleary-eyed drunks with their arms around each other’s shoulders at 1:59 everywhere, though: As it turns out, Wilson — who went on to earn Grammys for writing with Pink, the Dixie Chicks and Adele — was also writing about the impending birth of his first child with his then-girlfriend. But what you remember is that warm and fuzzy guitar, the song’s triumphant, still echoing refrain (c’mon, sing it: “I know who I want to take me home!”), and that tear-in-your-beer, scrawled-on-the-bathroom-stall-wall final line: “Every new beginning comes form some other beginning’s end.” -- G.K.

10. JAY-Z, "Hard Knock Life (Ghetto Anthem)" (No. 15, Hot 100)

There’s a reason the song’s subtitle is "Ghetto Anthem," and a reason it’s the title track to Jay’s third album Vol. 2: With this album, Jay had officially arrived, and he was then in a position to tell his story in a more universal way. Co-opting the "Hard Knock Life" refrain from Annie, Jay flipped the narrative in his direction and littered his verses with lyrical references and call-outs to other rappers and tracks, generally displaying the confidence and braggadocio that can only come from finally feeling comfortable with the climb to the top without forgetting the path from which you came. The song established Hov as an unquestionably dominant force in hip-hop, bearing out that confidence: It reached No. 15 on the Hot 100, his highest-charting song to date at that point, while the album became his first in a string of 14 No. 1 albums, the most in history for a solo artist. -- D.R.

9. Madonna, "Ray of Light" (No. 5, Hot 100)

The world seemed to be tiring of global superstar Madonna by the late '90s, so naturally, she responded by simultaneously re-conquering the planet and reaching new creative peaks. Working with British DJ-producer William Orbit and drawing on a 1971 folk song (Curtiss Maldoon's "Sepheryn") for lyrics, Madge gave radio its most joyous, ebullient and life-affirming dance banger since, well, maybe her own "Into the Groove" more than a decade prior. Yeah, the cool kids had been raving for years, but it took a trendsetting 39-year-old mom (who just happened to have 11 No. 1s to her name) to crack open the top 40 for what was then called electronica's eventual pop takeover. -- J.L.

8. Backstreet Boys, "Everybody (Backstreet's Back)" (No. 4, Hot 100)

By 1998, the Backstreet Boys were no longer the only ones: *NSYNC were already up and running, even working with the same producers. But with "Everybody," they were original, yeah, and a little sex-u-aaaal to boot, thanks to that soda-sticky synth bass that Scandi-pop wizards Max Martin and Denniz Pop cooked up to facilitate some interpersonal body-rockin'. (Never mind that Nick Carter was only 17 when he recorded that head-scratcher of a lyric.) The song, recorded for the group's second international LP, was originally excluded from their U.S. debut, as label execs worried that the lyrics about being "back again" might confuse first-time listeners. Yet the stomping track's fusion of European pop, American R&B, and stadium-rock-sized choruses is the perfect distillation of Cheiron Studios' iconic sound, and the song proved to be as good an introduction as any -- alright! -- N.F.

7. OutKast, "Rosa Parks" (No. 55, Hot 100)

Atlanta’s status as a creative hub of hip-hop was hardly a secret by the late '90s. Big Boi and Andre were prepping their third studio album with a handful of radio hits under their belts, three years removed from being famously booed at the Source Awards in New York for declaring, “The South got something to say.” Well, it did, and by the Aquemini sessions, both members had a lot to say on their own, too. 

Years before this led to the splintering of the group, Antwan and Three Stacks put their magic rings together for ’98’s Aquemini — a funky, spaced-out, national triumph — and “Rosa Parks” stands today as by far its biggest smash. Big Boi’s easy-ridin’ hook is the stuff of Sleepy Brown legend, and the weirdo ATL mission statement of his opening verse melds perfectly with Andre’s gypsy tale; that’s all before Andre’s stepfather, Rev. Robert Hodo, helps break it all down with his iconic harmonica solo during the front-porch-clap-along bridge. She didn’t approve at first, but even the real-life Rosa Parks eventually came around. -- C.P.

6. The Verve, "Bitter Sweet Symphony" (No. 12, Hot 100)

“Bitter Sweet Symphony” just feels like slow motion, with its sharp strings oozing brilliantly underneath the melancholy voice of Richard Ashcroft, making the listener as impervious to the outside world as Ashcroft himself was in the song's classic music video. That wasn't the only unforgettable visual the song's been paired with: It also memorably soundtracked the denouement of teen-drama cult favorite Cruel Intentions, and Reese Witherspoon's epic climactic destruction of Sarah Michele Gellar. The fact that it samples an orchestral version of the Rolling Stones' "Last Time" -- a move that proved costly for The Verve -- only means that it's easily the best song Mick Jagger and Keith Richards can claim to have "written" in the last 30 years. -- D.W.

5. Brandy & Monica, "The Boy Is Mine" (No. 1, Hot 100)

By the time Brandy and Monica linked up for “The Boy Is Mine,” each had built careers with mounting success. The former was already a few seasons deep into her titular role on her UPN show Moesha with a multi-platinum debut album to her credit, while the latter had stacked a handful of top 10 hits of her own throughout the ‘90s. But it was when their worlds collided that they hit a new stratosphere. On the Rodney “Darkchild” Jenkins-helmed duet, the rising divas went back and forth about ownership over a two-timing player who was seeing them both. Their vocals were mint, the production was almost altogether timeless, and the attitude was brought -- a perfect storm for success. “The Boy Is Mine” became both artists' first No. 1 on the Billboard Hot 100, spending 13 consecutive weeks at the top. And despite the fact that their rumored real-life rivalry could have undermined its momentum, it did anything but, becoming one of the most revered songs in either singer's catalog. -- S.J.H.

4. *NSYNC, "Tearin' Up My Heart" (No. 59, Hot 100)

Despite there being a dearth of superstar boy bands in 2018, in '98 there were seemingly countless teenage heartthrobs duking it out for pop supremacy. With their U.S. release of their self-titled debut in early 1998, *NSYNC surged ahead in the standings, and had the entire world dancing, singing, and humming every word of smash singles "I Want You Back" and "Tearing Up My Heart." The latter -- which smartly served as the album's opener -- was and remains an undeniable bop. Being conflicted in the agonizing game of love never sounded so good: Do you stay? Do you work things out in the name of love? Or do you just keep jamming to the blissful dance-pop in your flowing black-and-white outfit, and worry about all the romantic drama later? -- C.L.

3. Natalie Imbruglia, "Torn" (No. 42, Hot 100)

You can practically time your calendar to it: Every year or so, there'll be an article that sweeps through social media and reveals to readers the shocking truth: Natalie Imbruglia's "Torn" was a cover! Indeed, the heartbreak anthem that briefly brought the former Australian soap star to international stardom was originally written by members of Los Angeles alt-rock outfit Ednaswap in 1993, released first in Danish by pop singer Lis Sorensen, and then by Ednaswap themselves a few years later. Neither version found much commercial success, until the song found its way to Imbruglia's debut album, Left of the Middle, and went worldwide from there. The story is well-circulated at this point -- and yet, each time such an exposé makes the rounds, it's treated like breaking news. 

The reason for this isn't hard to suss out: Listening to Natalie Imbruglia's "Torn," it's unthinkable the song ever could've belonged to anyone else. Never mind that 20 years later, you still can't even see the word "Torn" without picturing Imbruglia twirling around her fake-studio apartment in her dragon A-shirt and khakis: The way she paces through the devastated lyric -- racing and panicked one second, distraught and almost inarticulate the next -- feels far too lived-in to possibly be borrowed. Every second of her "Torn" brings its own exquisite ruination, from the opened-curtains intro to the brutally succinct "Nothing's fine, I'm torn" chorus trigger and the soaring, weeping outro -- recently interpolated by Brockhampton, even. Unfortunately, the singer-songwriter was unable to replicate the success of "Torn," but when you nail it with the first song you write like this, it's pretty tough to recapture that magic. Wait a minute... "Torn" was a cover? Damn. -- A.U.

2. Lauryn Hill, "Doo Wop (That Thing!)" (No. 1, Hot 100)

It didn’t matter what street you turned down: This bouncy, head-bopping earworm was the song coming from everyone’s car in late 1998, warning listeners, to the tune of triumphant horns and a crisp piano hook, about being used for that thing -- be it sex, drugs, money, or otherwise. Lauryn Hill was hardly an unknown then, having already achieved major crossover success as one-third of mid-'90s rap group The Fugees. But it wasn’t long before "Doo Wop" -- the debut single off Hill’s now-iconic The Miseducation of Lauryn Hill LP -- and its soulful wisdom catapulted her to solo superstardom.

“Doo Wop,” which samples 5th Dimension’s 1971 track “Together Let’s Find Love,” earned the then-23-year-old her first (and to date only) Hot 100 No. 1 -- making her one of only five female rappers to ever rule the chart at all, and at the time, the very first to do so without any other billed artists. She also snagged two Grammys for the track, and the song’s memorable split-screen block party visual earned her four MTV Video Music Awards, including Video of the Year, making her the first MC to take home the show's top honors. 

But accolades aside, what remains most striking about “Doo Wop” is the egalitarian message woven into Hill’s ice-cold rhyming swagger. Far ahead of her time, Hill succeeded in offering a wise PSA to both sexes without pitting one against the other: While the first verse references Philadelphia’s Million Woman March and advises ladies not to “be a hard rock when you really are a gem,” the second takes on a man “more concerned with his rims and his Timbs” than treating a woman right, each with equal parts grit and groove. With her first bona fide hit, Hill didn’t just prove her own worth as a solo R&B/hip-hop artist. In perhaps her more important contribution to the genre, the song also proved that rap can be a tool to unite, and to empower. -- T.C.

1. Aaliyah, "Are You That Somebody?" (No. 21, Hot 100)

You can’t even find the song.

“Are You That Somebody?” is currently lost outside the stream of capital, thanks to the chicanery and stubborn grief of Aaliyah’s uncle and manager, Barry Hankerson. The digital streaming platforms don’t carry it, and the YouTube uploads aren’t beaming money to any label. On some level this is correct, because “Are You That Somebody?” should forever live in the beyond, as something to chase.

It’s of the past -- 20 years come June -- but still sounds like the future. Produced and written by Timbaland and Static Major and sung by Aaliyah, the song was recorded like a dream. At 4 a.m., Tim received a call from Hankerson, explaining that they needed a hit to put on the Dr. Doolittle soundtrack by 8 a.m. Talking animals and PG-13 Eddie Murphy? It hardly mattered -- the near-half-a-million bag beckoned and the great work began, with Timbaland hunched over a drum machine, Aaliyah in the booth, Static waving a blunt and smiling because he had the hook. They made the hit Hankerson asked for, and more.

Before you get to the baby, there’s the staccato bass line and drum sounds. You could stutter-step through the empty pockets left in the beat like you were dodging fat, lazy raindrops. The clucking and popping is a human mouth, only it’s tap dancing. “Boy,” Aaliyah begins like she’s creating a perfectly round bubble of sound, drawing out the vowel and vibrating it. The lyrics describe love like a secret, and if this boy is let in on it, he can’t tell nobody. Fifty-three seconds in, the baby pops out, right on time and totally uncalled for, a genuine moment of awe for the Hot 100, where the song would eventually peak at No. 21. Prince himself used the same sample to close out “Delirious” in 1982, but man, the chutzpah to let it coo repeatedly through this skeleton of a beat.

As Grammy-winning producer Bryan-Michael Cox told Vibe in 2008, “It ain’t been a record like that since.” A year later, Drake interpolated Static’s hook for Young Money’s “BedRock,” and one year after that, James Blake submerged and pitch-shifted Aaliyah’s voice for his breakout single “CMYK.” Like Sasha Frere-Jones wrote in The New Yorker, the song is “still effervescing” and inspiring new work, many years after the Grammys gave it a nod for best female R&B vocal performance. Ten out of ten people agree: This shit is not regular.

“Are You That Somebody?” persists in the cultural imagination despite being unavailable for sale on Amazon or iTunes, despite being unstreamable on Spotify or Tidal or Apple Music. Tens of millions of us know, by heart, a field recording of an infant made in 1969 -- an infant who will never be identified. Aaliyah passed away in August, of 2001. There is no way to tell her that nearly two decades later, “Somebody” remains like the secret cave her and Timabaland’s crews populate in the song’s video: sacred territory hidden in plain sight, accessible only to the two of them. -- R.S.