If 1997 was the seismic shift in the landscape of 90s music, ushering in a new era dominated by pop sensibilities and boy bands, then 1998 was the year this bold new world truly took center stage. The transition was complete, and the soundscape was richer and more diverse than ever.
The boy band phenomenon exploded, reaching unprecedented heights of popularity. Backstreet Boys and *NSYNC became household names, achieving diamond-selling albums and achieving a level of cultural saturation that few artists reach. Simultaneously, nu-metal emerged as the dominant force in rock, with bands like KoRn and Limp Bizkit injecting raw energy into an alternative scene that many felt had become too mainstream. Hip-hop in New York experienced a powerful resurgence, fueled by the blockbuster success of Puff Daddy and The Notorious B.I.G. the previous year. Icons like JAY-Z, DMX, and Big Punisher rose to superstardom, each bringing a unique flavor to the genre. The launch of MTV’s Total Request Live (TRL) became a pivotal moment, creating a central hub for young pop fans and fostering a dynamic ecosystem where these diverse genres could coexist and propel each other to even greater commercial success.
But even amidst these monumental shifts and the reign of pop titans, the true essence of 1998’s music scene lay in the eclectic mix of hits that orbited these central stars. These songs, often unexpected and genre-bending, gave 1998 its distinctive character. Aerosmith, after a quarter-century career, finally landed their first Billboard Hot 100 No. 1 single. The Fugees, though officially on hiatus, saw all three of their members achieve significant solo hits. Soundtracks from unlikely movies like Rush Hour, City of Angels, and Dr. Dolittle produced some of the year’s biggest songs. The iconic collaborations of Brandy & Monica and Whitney & Mariah defined the R&B landscape. Novelty hits like “Pretty Fly (For a White Guy)” and international sensations like “Du Hast” became inescapable. Even the swing revival had its moment in the sun. The 90s were roaring on the Billboard charts, a pre-millennial boom where no one could have foreseen the digital revolution just around the corner, poised to fundamentally alter the music industry.
At Billboard, we celebrated this incredible year with a deep dive into 1998, revisiting the unforgettable songs, artists, and cultural moments that defined it. We compiled a list of 98 favorite songs of ’98 – the tracks that best capture the spirit of that year and have resonated through the decades. Our criteria for inclusion were simple: songs released as singles in ’98 or songs that first charted on the Billboard charts in ’98. Songs that broke through the Hot 100 barrier in ’99, even if they debuted in ’98 (like “Ruff Ryders’ Anthem” or “Ex Factor”), or topped the charts in ’99 after a ’98 debut (like “Baby One More Time” or “Believe”), are recognized as songs for the year 1999.
Explore our curated list below – complete with a Spotify playlist at the end for your listening pleasure – and relive the era of Monica Lewinsky, Jesse Camp, and Mark McGwire as we journey back to 1998.
98. Donny Osmond & Chorus, “I’ll Make a Man Out of You” (Did not chart)
Let’s get straight to business: this is undeniably one of Disney’s greatest musical moments. While the song certainly navigates complex racial and gender stereotypes – Osmond voicing a Chinese character and the lyrics leaning heavily into traditional male and female roles – the sheer fun of Osmond’s smooth, almost sarcastic delivery of insults and commands, coupled with the resounding “BE A MAN!” chorus, is simply irresistible. It’s a testament to the song’s infectious energy that transcends potentially problematic elements. – DENISE WARNER
97. Jewel, “Hands” (No. 6, Hot 100)
Jewel successfully navigated the tricky sophomore album challenge with “Hands,” the lead single from her second album, Spirit. The song’s iconic music video, though perhaps unintentionally meme-worthy by today’s standards, featured Jewel serenely walking through the aftermath of a natural disaster while rescue workers aided victims. Despite the video’s somewhat jarring imagery, the song’s heartfelt and empowering lyrics remain resonant, echoing in modern anthems of resilience 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 intended to launch R&B newcomer Nicole Wray from her debut album of the same name. However, its undeniable Missy Elliott vibe propelled it to hit status. It felt less like a debut single and more like a standout bonus track from Missy’s groundbreaking Supa Dupa Fly album. This is no coincidence, considering Missy Elliott herself penned the song, Timbaland produced it, and their signature creeping beats and cool delivery are all over the track. Missy even contributes a rap verse, injecting extra star power into the 17-year-old Goldmind Records signee’s alluring debut single, helping it climb to the Top 5 of the Hot 100. – CHRISTINE WERTHMAN
95. Cherry Poppin’ Daddies, “Zoot Suit Riot” (No. 41, Radio Songs)
Amidst the wave of 90s genre revivals, Cherry Poppin’ Daddies and their inescapable hit “Zoot Suit Riot” stand as perhaps the most memorable artifact of the brief swing revival. Led by Steve Perry (not that Steve Perry, though imagine!), the band briefly graced the Billboard charts from early 1998 to early 1999. What a year it was, prompting pre-Google listeners to scramble to recall the Zoot Suit Riots (or even what a zoot suit was). Now, crack open a cold one and swing! – KEVIN RUTHERFORD
94. Deftones, “Be Quiet and Drive (Far Away)” (No. 29, Mainstream Rock)
Consider “Be Quiet and Drive (Far Away)” as the nu-metal generation’s version of The Smiths’ “There Is a Light That Never Goes Out.” Deftones’ thrashgaze masterpiece encapsulates a generation’s angst within a simple two-chord structure and minimal lyrics. While their hard rock contemporaries spent the late 90s and early 2000s vying to be the loudest and most explicit in expressing their angst, the Sacramento quintet understood the power of restraint. Frontman Chino Moreno’s guttural howl, “I don’t care where just FAR!!” perfectly captured a universal desire for escape. – ANDREW UNTERBERGER
93. Jo Dee Messina, “I’m Alright” (No. 43, Hot 100)
While female empowerment was a recurring theme among late 90s country artists, Jo Dee Messina’s “I’m Alright” took a more lighthearted approach, delivering a feel-good anthem that could lift anyone’s spirits. The lyrics “It’s a beautiful day, not a cloud in sight/ So I guess I’m doing alright” offer a timeless mood boost, amplified by Messina’s confident vocals and the song’s breezy tempo. “I’m Alright” became a classic for both country and pop fans, demonstrating the genre-blurring trends of 1998. – TAYLOR WEATHERBY
92. Puff Daddy feat. The Notorious B.I.G. & Busta Rhymes, “Victory” (No. 19, Hot 100)
Exactly one year and eight days after the tragic passing of Christopher Wallace, his friend and collaborator Sean “Puff Daddy” Combs released “Victory,” the final single from his blockbuster album No Way Out. “Victory” serves as the powerful opening track to Puff Daddy’s debut, and it’s a monumental statement. This is the kind of opener that could equally serve as a closer, a spectacular experience demanding an epic, eight-minute music video featuring cameos from Danny DeVito and Dennis Hopper. The Rocky-inspired sample, the building tension of strings and ringing bells, Puffy’s confident boasts interspersed with Biggie’s ad-libs – it’s all a prelude to the main event. Then, Biggie arrives with the poise and power of a champion boxer emerging from his corner: “In the Commission, you ask for permission to hit ’em.” Except for Biggie himself, of course. – ROSS SCARANO
91. JYP, “Honey” (Did not chart)
Opening with one of K-pop history’s most iconic, whining synth intros, J.Y. Park’s “Honey” exudes confidence from the outset with its funky brass riff and explosive horns. This track became an instant K-pop classic in 1998, and while J.Y. Park is now better known as the founder of JYP Entertainment, home to K-pop giants like TWICE and GOT7, the legacy of “Honey” endures. Countless covers by K-pop’s most popular acts demonstrate the song’s lasting impact and influence. – TAMAR HERMAN
90. Rob Zombie, “Dragula” (No. 6, Mainstream Rock)
For anyone who owned a PlayStation in the late 90s, Rob Zombie’s “Dragula” was practically synonymous with gaming. It became a staple in racing simulations during the console’s early years, and for good reason. Aside from perhaps Molly Hatchet’s “Flirtin’ with Disaster,” there’s no better song to soundtrack high-octane racing games, both then and now. And let’s not forget, the song is literally named after a drag-racing car from The Munsters. Fueled by one of nu-metal’s most memorable choruses and riffs that delivered a sonic punch every time, “Dragula” is pure adrenaline in song form. – K.R.
89. Shakira, “Ciega, Sordomuda” (No. 1, Latin Songs)
Shakira was already a Latin American star, but Dónde Están los Ladrones? propelled her to international recognition, breaking down borders and language barriers. “Ciega, Sordomuda,” a powerful pop-rock anthem boldly equating total love to being blind, deaf, and mute, defied the conventions of popular Latina music at the time. It became Shakira’s first No. 1 on Billboard’s Hot Latin Songs chart and served as the precursor to her groundbreaking crossover success in the English-speaking market. – LEILA COBO
88. Blink-182, “Josie” (Did not chart)
In the late 90s, Blink-182 became the voice of pop-punk for a post-Gen X generation too young for Dookie but still craving a raw, edgy alternative to mainstream rock acts like Sugar Ray and Eve 6. “Dammit” from Dude Ranch broke them in 1997, and a year later, “Josie,” a buzzsaw single from their major-label debut, solidified the Blink-182 brand: slapstick vocal interplay between Mark Hoppus and Tom DeLonge, rapid-fire drumming (from Scott Raynor, before Travis Barker), and lyrics pining for a cool, independent (and imaginary) girlfriend. References to their favorite Mexican food spot (Sombrero) and pop-punk peers Unwritten Law perfectly capture the San Diego vibe of 1998, beyond just the Padres’ World Series sweep by the Yankees. – CHRIS PAYNE
87. Beenie Man, “Who Am I” (No. 40, Hot 100)
Beenie Man had already earned respect in Jamaica through his role in 1997’s Dancehall Queen and party anthems like “Wickedest Slam” and “Romie.” But “Who Am I” brought his signature exaggerated “Woieee nah nah!” wails to a global audience. The track is one of dancehall’s few true pop-culture masterpieces, with Beenie Man playfully referencing Luther Vandross’ 1981 hit “Never Too Much” and Missy Elliott’s “The Rain (Supa Dupa Fly)” over a ground-shaking bassline. “Who Am I” was so beloved that Beenie Man later reimagined it as his 2000 track “Girls Dem Sugar,” a sensual duet with Mya and production by The Neptunes, further cementing the original’s iconic status. – BIANCA GRACIE
86. Alanis Morissette, “Uninvited” (No. 4, Radio Songs)
Alanis Morissette’s 1995 debut Jagged Little Pill remains her undisputed masterpiece, but “Uninvited,” the haunting single from the City of Angels soundtrack, built upon that album’s intensity and critical acclaim. The song earned her Grammys for Best Rock Song and Best Female Rock Vocal Performance and served as a powerful standalone hit, keeping fans engaged until the release of Supposed Former Infatuation Junkie later that year. “Uninvited” also dominated the charts, topping the Adult Mainstream Chart, her third single to achieve this after “Ironic” and “Head Over Feet.” – HILARY HUGHES
85. Monica, “The First Night” (No. 1, Hot 100)
Producer Jermaine Dupri’s brilliant decision to build Monica’s “The First Night” around Diana Ross’ 1976 disco classic “Love Hangover” practically guaranteed its success. While R&B artists often addressed abstinence through emotional ballads (think Janet Jackson’s “Let’s Wait Awhile”), Monica took a cooler, more assertive stance on not giving it up easily, all set to a thumping bassline. Her sassiness and self-assuredness in “The First Night” earned her a Hot 100 No. 1 hit and inspired a generation of female singers to stand their ground with persistent suitors. – B.G.
84. A Tribe Called Quest, “Find a Way” (No. 71, Hot 100)
With a new wave of New York rappers gaining prominence, A Tribe Called Quest felt somewhat like outsiders on 1998 radio, especially with “Find a Way,” arguably their most enigmatic single to date. This Love Movement single, produced by J Dilla, was a curious, hypnotic track with emotionally ambiguous lyrics about love and/or lust and a strangely dense chorus. Yet, the chorus was undeniably catchy, as evidenced by the bouncing-ball singalong in the song’s music video. “Find a Way” didn’t dominate the charts, but it remains etched in the memory of those who experienced it, a song as mysterious and captivating as the complex emotions it explored. – A.U.
83. Everclear, “Father of Mine” (No. 70, Hot 100)
Art Alexakis, the frontman of Everclear, was never afraid to lay bare his vulnerabilities. He addressed his struggles with addiction in hits like “Heroin Girl,” and “Father of Mine,” a swinging single from the band’s second major-label album, hit hard but with a gentler touch. Set against the band’s signature bouncy bubblegrunge sound, Alexakis revealed lingering anger and resentment towards his father who left when he was a child, a “scared white boy in a black neighborhood.” The most poignant line cuts deep: “Daddy gave me a name/ Then he walked away.” – GIL KAUFMAN
82. Wyclef Jean, “Gone Till November” (No. 7, Hot 100)
Following the global success of the Fugees’ The Score in 1996, each member embarked on solo endeavors. Wyclef Jean’s 1997 debut, The Carnival, showcased his versatility as a rapper, singer, and musician. “Gone Till November,” a standout single from the album, marked his most striking departure, a sweeping orchestral ballad offering solace to the loved ones of those living a hustler’s lifestyle. Lyrically poignant with heart-wrenching twists, it added a layer of tenderness to the Fugees’ raw honesty, providing comfort for long-distance relationships. – BRYAN KRESS?
81. Edwin McCain, “I’ll Be” (No. 5, Hot 100)
Long before Ed Sheeran’s chart-topping “Perfect,” Edwin McCain crafted “I’ll Be,” one of the most swoon-worthy and wedding-ready love songs of the 90s. The dynamic chorus, essentially a set of wedding vows (“I’ll be better when I’m older/ I’ll be the greatest fan of your life”), combined with McCain’s passionate delivery and a jazzy saxophone accompaniment, makes his declaration of love perfect for both a heartfelt singalong and a wedding dance floor, whether in 1998, 2018, or 2088. – T.W.
80. Air, “Sexy Boy” (No. 22, Dance Single Sales)
“Sexy Boy,” the lead single and standout track from Air’s enduring debut album, Moon Safari, showcases the French electronic duo at their crossover peak. Featured in the 1999 film 10 Things I Hate About You and the British TV series Queer as Folk, this dreamy and expansive downtempo track reached No. 22 on Billboard’s U.S. Dance/Electronic Singles Sales chart and propelled the critically acclaimed group to international fame. – MATT MEDVED
79. Tamia, “So Into You” (No. 30, Hot 100)
After establishing herself with a pair of hit ballads, Tamia shifted gears with “So Into You,” sampling The Commodores. The hook is the undeniable highlight, featuring buttery vocals perfectly synced with the drum pattern before Tamia effortlessly glides into a sweet high note. The chorus was so captivating that Fabolous sampled it for his hit “Into You,” a No. 4 Hot 100 success in 2003, and it was also prominently featured in Childish Gambino’s BBC Live 1 Lounge set in 2015. – TREVOR ANDERSON
78. Sheryl Crow, “My Favorite Mistake” (No. 20, Hot 100)
Sheryl Crow established herself as a guitar-driven rocker with her star-making 1993 debut Tuesday Night Music Club, effortlessly blending bluesy licks and power chords into pop songwriting. She refined this skill in her eponymous 1996 follow-up and even further in 1998’s The Globe Sessions. “My Favorite Mistake” arguably represents the peak of this skill set. Her toffee-toned vocals combined with the driving force of guitars and organs solidify her status as a true pop star in rocker’s clothing. – STEVEN J. HOROWITZ
77. Cake, “Never There” (No. 78, Hot 100)
While “The Distance” in 1996 was Cake’s breakthrough hit, “Never There” has arguably surpassed it in terms of pop-culture longevity, thanks to its universally relatable lyrics. The feeling of loving someone who is perpetually unavailable, leaving you with only the empty sound of a dial tone, is timeless. Cake successfully tapped into this emotion, hitting our emotional buttons like keys on a landline. – LYNDSEY HAVENS
76. Will Smith, “Miami” (No. 17, Hot 100)
Big Willie Style was Will Smith’s solo debut album, but with five albums as The Fresh Prince and three massive blockbuster film credits (Bad Boys, Independence Day, Men In Black) under his belt, he was far from a newcomer in 1997. This is likely why “Miami” dominated 1998, even as the album’s fifth single. Of course, it also helps that the song is an irresistible funk bop with iconic come-hither backup vocals: “Welcome to Miami / Bienvenidos a Miami” will always sound undeniably sexy. – JOE LYNCH
75. Moby, “Honey” (No. 49, Dance Single Sales)
While Moby’s timeless Play LP is best known for international hits like “Porcelain” and “Natural Blues,” its opener and lead single, “Honey,” deserves equal recognition. Featuring bluesy looped vocal samples from U.S. folk singer Bessie Jones’ “Sometimes” over driving piano and slide guitar, the track briefly charted on Billboard’s U.S. Dance/Electronic Singles Sales chart. More importantly, it kicked 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, moving away from the rap-rock of his previous group Seo Taiji and Boys. While his self-titled album had heavy metal influences from his early days, “Take Five” adopted a sunnier disposition with hints of late-90s college rock. “Take Five” was intended as a message to fans, signaling his return to music after a retirement announcement in 1996. – CAITLIN KELLEY
73. Boards of Canada, “ROYGBIV” (Did not chart)
“ROYGBIV” could aptly describe almost any Boards of Canada song. Their brand of effervescent downtempo music is both polychromatic and naturalistic, evoking a rainbow within its sonic atmosphere. However, this two-and-a-half-minute instrumental is prismatic even by their high standards: simple, stunning, and organized with impossible geometric precision. Like all fleetingly beautiful phenomena, it vanishes far too quickly. – 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 coy with overtly sensual. But it was his third single, “My Way,” that solidified his persona as a freaky philanderer, the original Mr. Steal Your Girl: “She likes it my way,” Usher croons over a driving beat and ad-libs from Jermaine Dupri, one of the album’s co-producers. His boastful attitude and the song’s infectious bounce have stood the test of time. The music video, however, with Usher dressed in a bizarre Clockwork Orange-esque outfit squaring off against Tyrese in a junkyard (complete with a bounce house), is perhaps less timeless. – C.W.
71. Janet Jackson, “Go Deep” (No. 28, Radio Songs)
“Go Deep” is more than just a party starter; it’s a self-contained party in song form. From the opening crowd murmurs to the singalong chorus, the track exudes a loose, irresistible vibe. The infectious snare intro and playful sound effects create a danceable energy, perfectly mirroring the music video’s foamy house party, hilariously interrupted by a pre-SNL Bill Hader as a pizza delivery boy. – 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 toned down some of the original’s menacing funk, but compensated with new attitude-filled verses from Missy Elliott, a moody, Björk-sampling coda from Timbaland, and even some random horse neighs for good measure. One constant was Lil’ Kim’s fiery opening verse, remaining one of her best guest appearances, packed with quirky pop-culture references (Finnegan’s Wake! Sarafina!) and tongue-twisting lines 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 of an unknown Puerto Rican merengue singer was both 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, a rare feat for a Spanish-language album, especially a merengue album. Remixed countless times, this evergreen party track has been played everywhere from Egypt to Australia, and even the moon. “Suavemente” was the only Spanish-language song chosen by astronauts for the 2006 Discovery mission. – L.C.
68. Brian McKnight, “Anytime” (No. 6, Radio Songs)
It’s difficult to discuss Brian McKnight’s “Anytime” without lamenting the lack of similar songs in contemporary music. The nocturnal ballad possesses a delicate stillness almost antithetical to the streaming era and modern radio. McKnight’s soft chorus cry – “Do I ever cross your mind… anytime?” – is more understated than dramatic, accompanied by a Bruce Hornsby-esque piano loop. Only in the bridge does he unleash, revealing nights of crying himself to sleep, pleading for her return – but quickly receding, leaving only the devastating simplicity of “I miss you.” – A.U.
67. Sarah McLachlan, “Angel” (No. 4, Hot 100)
Despite its frequent use in TV specials, films, and commercials, the hauntingly real origin of “Angel” should not be forgotten. McLachlan wrote the song in response to the heroin overdose death of Smashing Pumpkins touring keyboardist Jonathan Melvoin and the increasing number of musicians turning to drugs to cope with industry pressures (“Fly away from here/ From this dark, cold hotel room”). This specificity enhances the song’s poignancy, preventing it from becoming a generic ballad and adding depth to its emotional core. – T.A.
66. Elliott Smith, “Waltz No. 2” (Did not chart)
In contrast to Smith’s typically hushed, downtempo singles, “Waltz No. 2,” the lead single from his fourth album XO, explores a richer, fuller sound. The jangly production and Smith’s trembling vocals create a well-crafted and arguably more accessible track from the intensely intimate indie-rock icon. The timelessly poignant line “I’m never gonna know you now/ But I’m gonna love you anyhow” continues to resonate deeply. – L.H.
65. K-Ci & JoJo, “All My Life” (No. 1, Hot 100)
Typically, being told your love reminds someone of their mother, father, brother, and sister is a red flag. However, K-Ci & JoJo were sincere in declaring that one lucky woman was their everything. They delivered this sentiment with a yearning chorus that proved K-Ci and JoJo were more than just members of Jodeci filling time during a hiatus. While the sentiment might be cheesy, the high-quality songwriting is timeless. It’s no wonder fragments of “All My Life” continue to surface in contemporary hits. – N.F.
64. Rammstein, “Du Hast” (No. 20, Mainstream Rock)
Every year seems to have a breakthrough hit from a German industrial-metal band, and 1998 was no exception. Wait, really? Yes, for some reason, 1998 saw a metal sextet from Berlin break into TRL and the American charts with an industrial track infused with 90s house and operetta influences. The German wordplay – “duhast mich” (you have me) and “du hasst mich” (you hate me) sound identical – was lost on most U.S. listeners, but the song’s meaty guitar riff transcended language barriers. – J.L.
63. Whitney Houston & Mariah Carey, “When You Believe” (No. 15, Hot 100)
What happens when two of the 90s biggest powerhouse divas collaborate for a major motion picture soundtrack? Surprisingly, a fairly traditional, saccharine power ballad. But no criticism intended: Whitney and Mariah sound phenomenal trading verses, and their harmonies are flawless. While the song only reached No. 15 on the Hot 100, the pair had the last laugh: this Prince of Egypt track won the Academy Award for Best Original Song. – P.C.
62. All Saints, “Never Ever” (No. 4, Hot 100)
Spice Girls aside, numerous UK girl groups remained largely unknown in the US during the late 90s. However, All Saints’ “Never Ever” managed to break through on US radio, thanks to its catchy chorus and earnest spoken-word intro. While some lyrics may be slightly awkward (the “shower”/”scour” rhyme), the song served a public service by introducing American audiences to the proper British pronunciation of “Z.” – K.A.
61. Goo Goo Dolls, “Slide” (No. 8, Hot 100)
While its soundtrack predecessor propelled the band to household name status, “Slide” proved that Goo Goo Dolls were still masters at crafting songs that bridged adult rock and adult contemporary. “Put your arms around me/ What you feel is what you are, and what you are is beautiful,” frontman Johnny Rzeznik belts with urgency and heartfelt sincerity, perfectly capturing the fraught young relationship described in the verses. It was clear that Goo Goo Dolls were determined to avoid being labeled as one-hit wonders. – A.U.
60. N.O.R.E., “SuperThug (What What)” (No. 36, Hot 100)
The helicopter whirring at the beginning signals the arrival of the artist who would shape pop music at the turn of the millennium. Not necessarily Noreaga (though he has more classic singles than you might realize, starting with this one), but rather the production duo The Neptunes. Their groundbreaking beat for “SuperThug” blended old-school hardness with electro-funk futurism and New Jack Swing hooks (and even a Puffy-esque “Heart of Glass” lift), resulting in one of the most potent hip-hop singles of the late 90s. This was just the beginning of what was to come, thankfully. – A.U.
59. Radiohead, “No Surprises” (Did not chart)
Before Radiohead became pioneers of dystopian electronic music, they crafted melancholic, visionary rock that could soundtrack any mental breakdown. Pairing fatalistic grievances (“a job that slowly kills you”) with the visual of Thom Yorke’s stoic face submerged in a water tank, “No Surprises” subtly conveys existential dread through a deceptively pleasant guitar melody. The “final fit” offers a sense of release, like breaking the surface just in time. – B.K.
58. Massive Attack, “Teardrop” (Did not chart)
While its American legacy began as the theme song for House, “Teardrop” was Massive Attack’s first – and only – top 10 hit in the UK six years prior. The trip-hop trio’s most accessible hook certainly contributed to its success, but the details elevate the song: Liz Fraser’s delicate vocals, stormy piano chords, and haunting harpsichord riff. It’s atmospheric dejection perfected, explaining why music supervisors still gravitate towards it. – K.R.
57. Faith Hill, “This Kiss” (No. 7, Hot 100)
For anyone who’s experienced falling in love, “This Kiss” perfectly captures the joyous, surreal feeling of kissing someone special. Faith Hill’s smooth vocals embody the universal emotion that words often fail to express, making it easy for listeners to sing along to the infectious refrain as if it were their own story. Still a radio staple, “This Kiss” paved the way for Hill’s country icon status and became her first top 10 hit on both the Hot 100 and AC charts. – GAIL MITCHELL
56. Barenaked Ladies, “One Week” (No. 1, Hot 100)
“One Week” is a song that feels uniquely tied to the late 90s American pop music scene. A catchy, guitar-driven confessional with a tongue-in-cheek tone and verses that owe more to rap than traditional rock, it’s a quintessential snapshot of the melting pot that was late-90s mainstream music. Adding to its 90s credentials, it was even parodied by Weird Al, arguably even surpassing 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 their platinum-certified sophomore album Version 2.0, live in May 1998. By September, it was climbing the US Alternative Songs chart, driven by its killer electric bassline, inspired 60s pop interpolation, and Shirley Manson’s cleverly distorted vocals. The song also appeared in the first Rock Band video game, introducing Garbage to a new generation of millennials. – GAB GINSBERG
54. Backstreet Boys, “As Long As You Love Me” (No. 4, Radio Songs)
While Backstreet Boys had already achieved international success with “Quit Playing Games With My Heart,” they hadn’t truly showcased their sentimental side with a single until “As Long As You Love Me.” This track proved they could be sappy without sacrificing their energetic pop sound. It also highlighted their impressive harmonizing abilities, solidifying BSB as more than just a group of heartthrobs with catchy tunes. – T.W.
53. Eve 6, “Inside Out” (No. 28, Hot 100)
“Inside Out” is a quintessential example of inoffensive, radio-ready rock that dominated the 90s, from Spin Doctors’ “Two Princes” to Blessid Union of Souls’ “Hey Leonardo.” The genre’s peak was defined by instantly catchy hooks that dared you to sing along, even with a dictionary’s worth of words crammed into them. With words like “oblivion” and “rendezvous” haphazardly thrown into the nonsensical hook, this song challenges even the most skilled karaoke enthusiasts – yet remains irresistible to try. – P.C.
52. Lord Tariq & Peter Gunz, “Deja Vu (Uptown Baby)” (No. 9, Hot 100)
In a surprising twist, Donald Fagen of Steely Dan, known for his jazz snobbery, is credited as a writer on “Deja Vu (Uptown Baby),” including the lyric “cuz I’m quick to slide off and slide this dick up in your wife.” Peter Gunz of the Bronx delivers the line with finesse on this ode to hip-hop’s birthplace. The song samples Steely Dan’s “Black Cow,” transforming the past into the present. Despite the unorthodox publishing arrangement, the fat bassline and guitar lick still resonate, reminding us of rap music’s transformative power and the industry’s sometimes-dirty side. – R.S.
51. Lenny Kravitz, “Fly Away” (No. 12, Hot 100)
Lenny Kravitz had established himself as a modern-rock mainstay with “Are You Gonna Go My Way” in 1993, but then seemed to fade from the mainstream conversation – until “Fly Away,” the fourth single from 1998’s 5. This track became an unavoidable crossover smash. A simple, guitar-heavy song with an electric hook about wanting to escape – be it New York City, the world, or the news – “Fly Away” earned him his second top 10 radio hit and his first Grammy for Best Male Rock Vocal Performance, a category he would win again in 1999 and 2000. – XANDER ZELLNER
50. Third Eye Blind, “Jumper” (No. 5, Hot 100)
In an era where angst dominated the Billboard Hot 100, 3EB’s Stephan Jenkins was the king of pain. This creamy slice of acoustic power-pop, featuring a killer wah-wah guitar solo and surprisingly empathetic lyrics about desperation, continues to resonate today. Often called the band’s “suicide song,” it’s truly a longing prayer for connection, hope, and second chances. If teen angst ever needed an anthem, this is it. – G.K.
49. Uhm Jung Hwa, “Invitation” (Did not chart)
“Invitation,” Uhm Jung Hwa’s alluring 1998 hit, is characterized by breathy vocals and sleek synths. Written by J.Y. Park, the song showcases his signature smooth grooves. With dreamy sensuality and angsty raps from g.o.d’s Joon Park and Danny Ahn, “Invitation” remains one of the most memorable Korean songs from the 90s, and Uhm still performs it regularly. – T.H.
48. The LOX feat. Lil Kim & DMX, “Money, Power & Respect” (No. 17, Hot 100)
In 1998, New York rap was defined by grit and grime. Dark hoodies, Timberlands, and FUBU jerseys were the uniform of Gotham. While JAY-Z and DMX led the charge with their hard-hitting styles, The LOX cemented their place in Big Apple hip-hop history with “Money, Power & Respect.” The Yonkers trio relentlessly targets rap pretenders with their gritty delivery, while DMX adds a pulverizing verse and Lil’ Kim delivers the essential “key to life” hook. Twenty years later, “Money, Power & Respect” remains the unwritten code in hip-hop. – CARL LAMARRE
47. Marilyn Manson, “The Dope Show” (No. 15, Alternative Songs)
Marilyn Manson went pop? Sort of. Upon the release of “The Dope Show,” it was hard to say what was more shocking: Manson’s glam-rock stomp or his androgynous Hollywood alien look in the video. The song was more electronic and slinky than previous Manson tracks, but still retained the dark, rock power chords of songs like “The Beautiful People.” While more melodic and accessible, it wasn’t entirely unexpected: Manson had already covered “Sweet Dreams (Are Made of This)” and (eventually) “Tainted Love.” – C.W.
46. Deborah Cox, “Nobody’s Supposed to Be Here” (No. 2, Hot 100)
In the era of Mary J. Blige, Mariah Carey, and Whitney Houston, breaking through with a big ballad was a challenge. Deborah Cox’s “Nobody’s Supposed to Be Here” defied the odds, setting a record on the R&B charts. Co-written by Montell Jordan, the song held the top spot on Hot R&B/Hip-Hop Songs for 14 weeks. A textbook example of R&B-gospel fusion, “Nobody’s Supposed to Be Here” depicts a heartbroken woman finding love again, culminating in an extended high note that has intimidated reality competition hopefuls for decades. – T.A.
45. Neutral Milk Hotel, “Holland 1945” (Did not chart)
On the surface, “Holland, 1945” fits into the fuzz rock of the post-grunge indie era. However, digging into Jeff Mangum’s lyrics reveals a uniquely sincere ode to Holocaust victim Anne Frank, central to the band’s seminal album In The Aeroplane Over The Sea. Beyond any mainstream recognition, Neutral Milk Hotel’s work remains relevant as an early blueprint for bookish indie rock that distorts past and present to create a world uniquely its own. – B.K.
44. Ricky Martin, “The Cup of Life” (No. 45, Hot 100)
Ricky Martin exploded into mainstream consciousness in 1999 with a performance of “The Cup of Life” at the Grammy Awards. While “The Cup” didn’t dominate the Hot 100 (peaking at No. 45 in 1998 and again in 1999), it ignited the original “Latin Explosion” in English-language pop, paving the way for Shakira, Marc Anthony, Jennifer Lopez, and Enrique Iglesias. 1998 became a pivotal year for Latin music. “The Cup of Life” remains the most iconic World Cup anthem in modern history, setting the stage for the competitive quest for subsequent World Cup songs. 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)
The mesmerizing opening beats of “Love Like This” instantly draw you into what has become a party, club, and skating-rink classic. The latter even serves as the backdrop for the song’s video, with skaters moving to its mellow groove and Faith Evans’ smooth vocals. A compelling precursor to the R&B and hip-hop fusion that would dominate Top 40, Evans’ Grammy-nominated hit undoubtedly celebrates her romance with the late Notorious B.I.G., who passed away the year prior. – G.M.
42. D’Angelo, “Devil’s Pie” (No. 69, Hip-Hop/R&B Airplay)
“Devil’s Pie” is loose, low-key, and yet pointed in its themes. Some see it as an attack on materialism, others as an indictment of capitalism. D’Angelo himself compared its feel to the chants of a chain gang or slaves in a field. With biblical and apocalyptic undertones, it can be interpreted as a commentary on the trials people endure for perceived gains, often perpetuating cycles of repression. D’Angelo conveys this complex message without overtly stating it, allowing listeners to lose themselves in the improvisational flow. – D.R.
41. Master P feat. Fiend, Silkk the Shocker, Mia X & Mystikal, “Make ‘Em Say Uhh!” (No. 16, Hot 100)
It takes a collective effort to transform a local label into a global phenomenon. Master P and his No Limit soldiers took their New Orleans-based label from regional institution to the Bad Boy of the South with “Make ‘Em Say Uhh.” The breakthrough hit featured the label’s heavy hitters at their peak, laying the foundation for the song’s bleating horns and infectious singalong chorus. Even decades later, the sound of the tank rolling in still demands respect. – A.U.
40. Shania Twain, “You’re Still the One” (No. 2, Hot 100)
By 1998, Shania Twain was already a major country star with five Hot Country Songs No. 1s. However, “You’re Still the One” marked a new level of success, reaching No. 2 on the Hot 100 and solidifying her status as a superstar beyond country music. While Twain has had numerous hits since, nothing evokes the same feelings as her breathy vocals on the piano-tinged verses and the powerful build-up to the chorus. For couples who soundtracked their weddings with this song in 1998, Twain likely remains “the one” for musical romance two decades later. – T.W.
39. Usher, “Nice & Slow” (No. 1, Hot 100)
Credit Jermaine Dupri and the Casey twins of Jagged Edge for crafting one of the freakiest R&B slow jams of all time. Usher’s “Nice & Slow” is likely responsible for the conception of countless individuals. The ballad drips with sex appeal, with a young Usher detailing his plans for making love, even spelling out his 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, Usher channeled the confidence of R&B greats, his tender vocals caressing the song’s languid production. “Nice & Slow” became Usher’s first Hot 100 No. 1 and likely remains on many “get it on” playlists. – B.G.
38. The Offspring, “Pretty Fly (For a White Guy)” (No. 53, Hot 100)
Following the artifice of the 80s, being labeled a poser was a major insult in the 90s. The Offspring eviscerated wannabes with their ubiquitous rock-radio hit “Pretty Fly (For a White Guy),” an O.C. punk anthem sampling Def Leppard, referencing Ricki Lake, and satirizing kids who claimed to love hip-hop but listened to Vanilla Ice. Few songs are as sonically tied to their era, but the delivery – more smirk than fury – gives it a timeless quality. – J.L.
37. Aerosmith, “I Don’t Want to Miss a Thing” (No. 1, Hot 100)
Aerosmith’s catalog is full of classic rock anthems, but they didn’t achieve their first Hot 100 No. 1 until “I Don’t Want to Miss A Thing,” holding the top spot for four weeks. The Diane Warren-penned single for the Armageddon soundtrack, starring Steven Tyler’s daughter Liv, delivered one of Tyler’s most impressive vocal performances and became a slow-dance staple. The platinum-certified family affair earned an MTV Moonman, a Grammy nomination, and Aerosmith’s first Oscar nod in 1999. – H.H.
36. Fastball, “The Way” (No. 5, Radio Songs)
In the tradition of radio hits that sound happier than their origins, “The Way” was inspired by the tragic story of an elderly couple whose aimless road trip ended with their car plunging off a cliff. The song’s deceptive brilliance lies in its catchy melody and singalong lyrics, masking the tragic narrative: “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 after Reasonable Doubt, JAY-Z maintained momentum with Vol. 2…Hard Knock Life. Solidifying his rap titan status, Jay enlisted Amil and Ja Rule for “Can I Get A…”. While JAY-Z’s verse resonated in clubs, Amil’s swagger and Ja Rule’s rugged style stole the show. The song’s infectious hook remains a fixture at summer brunches and after-hour spots. Grab a drink and bounce with Jigga. – C.L.
34. KoRn, “Got the Life” (No. 15, Mainstream Rock)
“Got the Life” proved nu-metal’s power in the late 90s music scene. An absolute juggernaut: a ripping guitar riff over a chugging bass groove, anchored by Jonathan Davis’s vocal performance. He howls, whimpers, and scats, questioning God and facing a harsh reality: “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 soon understand. – A.U.
33. Next, “Too Close” (No. 1, Hot 100)
This sexy track about physical proximity combines a melodic mid-tempo beat with a sly, mischievous hook that left listeners questioning the 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 smooth harmonies, the R&B trio reached platinum status and No. 1 on the Hot 100 and R&B charts. – G.M.
32. Spice Girls, “Stop” (No. 16, Hot 100)
The Spice Girls embraced kitsch. By 1996’s Spice, they’d moved from girl-power anthems (“Wannabe”) to shiny pop bangers (“Say You’ll Be There”). Known for taking chances, “Stop” from 1997’s Spiceworld was all pomp and circumstance, the perfect movie montage soundtrack. – S.J.H.
31. Madonna, “Frozen” (No. 2, Hot 100)
The lead single from Ray of Light, “Frozen,” is a William Orbit-produced electro-pop masterpiece, arguably aging better than any Madonna hit since. Released before her 40th birthday and shortly after becoming a mother, the lyrics and lush production showcase a wiser, more mature Madonna. “If I could melt your heart,” she sings, and with “Frozen,” she does. – FRANK DIGIACOMO
30. Eagle-Eye Cherry, “Save Tonight” (No. 5, Hot 100)
Eagle-Eye Cherry, son of jazz trumpeter Don Cherry, debuted firmly in pop with “Save Tonight,” courting Top 40 radio with driving acoustics and a catchy chorus. Despite his debut album Desireless and subsequent releases, Eagle-Eye remained a one-hit wonder. However, his teary-eyed one-night stand anthem was a massive hit (peaking at No. 5), securing its place in 90s Night playlists. – C.P.
29. Dixie Chicks, “Wide Open Spaces” (No. 41, Hot 100)
The title track from their fourth album, “Wide Open Spaces,” marked the Dixie Chicks’ breakthrough with lead vocalist Natalie Maines. Featuring beautiful harmonies, an angsty-hopeful storyline, and a twangy violin solo, this hit led a diamond-certified album, proving there was plenty of space for women in country music. – D.W.
28. Stardust, “Music Sounds Better With You” (No. 62, Hot 100)
This 1998 dance-club gem is often mistaken for Daft Punk. While Daft Punk used it in their Alive 2007 tour, Stardust is a trio featuring only one-half of Daft Punk, Thomas Bangalter, with Alan Braxe and Benjamin Diamond. A dance floor filler, topping Billboard’s Dance Club Songs chart and cracking the Hot 100, “Music Sounds Better With You” boasts Daft Punk’s early hallmarks, inspiring copycat releases. Bangalter declined $3 million for a full Stardust album, making this anomaly one of dance music’s beloved one-hit wonders. – M.M.
27. Jennifer Paige, “Crush” (No. 3, Hot 100)
Before Britney Spears and Christina Aguilera dominated with bubblegum pop, Jennifer Paige played a key role in shaping the Y2K pop sound with her debut single “Crush.” With a “not that serious” attitude and soulful vocals, she casually dismissed a suitor: “Don’t make a fuss / And go crazy over you and me.” “Crush” became a transatlantic hit, and while Paige’s sound has evolved, the unforgettable “sha-la-la-la” intro remains iconic. – B.G.
26. Mariah Carey feat. Bone Thugs n Harmony, “Breakdown” (No. 53, Radio Songs)
The soul ballad that starts gently then explodes with heartbreak, “Breakdown” is elevated by Mariah Carey’s performance. The lyrics tell the story: “You called yesterday to basically say/ That you care for me but you’re just not in love.” Mariah, knowing her strengths, claims to feel the same, even though it’s “pretending.” Bone Thugs-n-Harmony’s Krayzie Bone and Wish Bone add controlled verses. By 3:10, Mariah’s mask slips, riffing and wailing, “How do I feel? I’m losing my mind.” If you don’t get chills, you might not understand life, loss, and R&B. – R.S.
25. Janet Jackson, “I Get Lonely” (No. 3, Hot 100)
Desperation isn’t typically sexy, but Janet Jackson makes it so in “I Get Lonely.” Over a Jimmy Jam and Terry Lewis beat, she sings about loneliness with a snap and glide that makes you move despite vulnerability. From The Velvet Rope, “Lonely” hits all the right notes: a multi-layered chorus plainly stating her feelings, verses of waiting by the phone, and a breakdown where she coos “gonna break it down.” The chorus, repeated six times with the same insistent lyrics, provides repeated release, a Janet Jackson specialty. – C.W.
24. Goo Goo Dolls, “Iris” (No. 9, Hot 100)
“Iris,” from the City of Angels soundtrack, is a blockbuster doe-eyed drama distilled into a five-minute rock ballad. Johnny Rzeznik’s lyrics mirror Nicholas Cage’s lovelorn angel: “You’re the closest to heaven that I’ll ever be.” Before commercial release, it topped Billboard’s Radio Songs chart for 18 weeks and Mainstream Top 40 for four. Twenty years later, the magic remains: acoustic guitar and mandolin interplay, lingering bass notes, and a soaring electric solo. They don’t make ballads like this anymore. – C.P.
23. DMX feat. Sheek, “Get at Me Dog” (No. 39, Hot 100)
“Where my dogs at?” Everywhere, soon. “Get at Me Dog” launched DMX to stardom and It’s Dark and Hell Is Hot to the top of the Billboard 200, the first of four consecutive chart-toppers. Ferocious even before the rapper’s barks at the chorus’ end, few breakthrough singles are this focused, determined, and nasty. Credit X and producer Dame Grease, who called it “the first song of the bring-it-back-to-the-streets era” in a Hell Is Hot oral history. – A.U.
22. Marcy Playground, “Sex & Candy” (No. 8, Hot 100)
Marcy Playground’s quirky hit “Sex & Candy” spent 15 weeks atop the Alternative Songs chart, making little sense. Inspired by a comment about post-coital smells, phrases like “platform double-suede” and “disco lemonade” remain alt-rock “covfefe.” While MP remained a one-hit wonder, “S&C” marks the end of an era where grunge remnants and teen-pop revolution coexisted. – G.K.
21. Will Smith, “Gettin’ Jiggy Wit It” (No. 1, Hot 100)
“Gettin’ Jiggy Wit It” is quintessential dad rap. Will Smith brags about dance moves over a Sister Sledge sample, pretends to smoke cigars (“it’s for the look”), and charms a woman with a “Prada bag.” The G-rated brother to “Miami,” it’s a song you might eye-roll at but can’t help dancing to. The MTV VMA-winning video is equally entertaining. Meaningless fun, it topped the Hot 100 for three weeks in 1998. – T.C.
20. Harvey Danger, “Flagpole Sitta” (No. 38, Radio Songs)
Harvey Danger’s “Flagpole Sitta” is one of the most memorable alt-rock radio hits of the 90s, an ode to hipsters and “raging against machines.” Still relevant, it embodies an era, shaking a fist at television and the tech boom, preferring to “publish ‘zines” or get a tongue piercing. Ironically, this anti-anthem went mainstream, reaching No. 3 on Alternative Songs and Top 40 on Radio Songs. Sean Nelson explained its shelf life due to self-awareness: “it is really conscious of the fact it is a piece of garbage.” – X.Z.
19. Big Punisher, “Still Not a Player” (No. 24, Hot 100)
“Still Not A Player,” by Big Punisher and Joe, was ahead of hip-hop’s mainstream pop pivot. A sequel to “I’m Not a Player,” it was two decades ahead of trends where remixes surpass originals and Top 40 hits blend Spanish and English. Whether a promise of faithfulness or wordplay (“I’m not a player I just fuck a lot”), it propelled Pun’s debut Capital Punishment to No. 5 on the Billboard 200, becoming the first Latin hip-hop platinum album. – B.K.
18. Fatboy Slim, “The Rockefeller Skank” (No. 76, Hot 100)
Fatboy Slim’s “The Rockefeller Skank” melded surf guitar, hip-hop, funk, and process music into a dance anthem. Endless TV and trailer appearances have diluted its impact, but initially, it was unprecedented in mainstream music. Listeners genuinely thought their CD players were skipping at the end’s seemingly endless vocal loop. – J.L.
17. Pras feat. Mya & Ol’ Dirty Bastard, “Ghetto Supastar (That Is What You Are)” (No. 15, Hot 100)
Ol’ Dirty Bastard on a song repurposing Dolly Parton and Kenny Rogers’ “Islands in the Stream” sounds like a skit, but incongruity made “Ghetto Supastar” irresistible in 1998. From the Bulworth soundtrack, this hip-pop confection alternates between Mya’s sweet vocals and Pras and ODB’s rhymes. The music blends Lalo Schifrin and Queen, with sonic gifts like ODB’s “in the hooooooood” and a fuzzy guitar solo. – F.D.
16. New Radicals, “You Get What You Give” (No. 36, Hot 100)
“You Get What You Give” is a great pop song for many reasons. Clever lyrics, including the “frenemies” portmanteau, are sincere platitudes empowering young fans to 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.” The “machine” includes health insurance, the FDA, and bankers. Despite dense lyrics, it’s infectious, thanks to Gregg Alexander, who, despite dissolving New Radicals after one album, remains a successful producer and songwriter. — K.A.
15. 2Pac, “Changes” (No. 32, Hot 100)
Released from his Greatest Hits set, “Changes” became a cultural touchstone, commenting on racial injustice, police brutality, and packed penitentiaries – issues arguably more prevalent today. In ’98, pre-Obama, 2Pac stated: “We ain’t ready to see a black president,” foreshadowing post-Obama realities. While Pac pleads for change over Bruce Hornsby-borrowed keys, the resignation of “That’s just the way it is” hits hardest, then and now. – L.H.
14. Celine Dion, “My Heart Will Go On” (No. 1, Hot 100)
Talent shows were forever changed. Celine Dion, despite vocal powerhouses like “The Power of Love,” topped herself with “My Heart Will Go On,” marrying everything loved (or hated) about Dion: breathy whispers, building crescendos, making cynics believe in good again. The James Horner- and Will Jennings-penned song debuted at No. 1, earned an Oscar and Grammys for record and song of the year. Appreciation continues, with Dion revisiting it on award shows decades later. “My Heart Will Go On” will endure. – T.A.
13. Hole, “Celebrity Skin” (No. 85, Hot 100)
With three power chords and a threatening “Oh, make me over,” Courtney Love propelled Hole from alt-rock heroes to TRL contenders. Co-written by Billy Corgan, the title track from their third album condemned fame and beauty standards on a grunge platter. Its deafening sound, sarcasm, and singalong chorus hooked listeners, topping the Alternative Songs chart and breaking the Billboard 200 top ten. – H.H.
12. Beastie Boys, “Intergalactic” (No. 28, Hot 100)
Decades before EDM’s vocal chops, Beastie Boys used a vocoder and two words to ignite dance floors. Once the beat drops, escape is impossible from goofy rhymes and one-liners that remain schoolyard-rhyme easy. Hello Nasty’s lead single hit Billboard’s pop, rhythmic, alternative, and mainstream rock charts simultaneously. 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.” Turning a bartender’s line into a signature hook is “forever money.” Dan Wilson’s “Closing Time,” an ode to last call, spent 25 weeks on the Adult Alternative Song charts. More than a bar anthem, Wilson wrote about his first child’s impending birth. But what resonates is the warm guitar, triumphant refrain (“I know who I want to take me home!”), and tear-in-your-beer 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)
“Hard Knock Life (Ghetto Anthem)” is titled “Ghetto Anthem” for a reason. By Vol. 2, Jay had arrived, telling his story universally. Co-opting “Hard Knock Life” from Annie, Jay flipped the narrative, referencing other rappers and tracks, displaying confidence from his climb to the top. Establishing Hov as a hip-hop force, it reached No. 15 on the Hot 100 and launched a string of 14 No. 1 albums. – D.R.
9. Madonna, “Ray of Light” (No. 5, Hot 100)
The world seemed tiring of Madonna, so she re-conquered it and reached new creative heights. Working with William Orbit and drawing on a 1971 folk song, Madonna delivered a joyous, life-affirming dance banger. Cool kids had been raving for years, but Madonna, a 39-year-old mom with 11 No. 1s, cracked open the top 40 for electronica’s pop takeover. – J.L.
8. Backstreet Boys, “Everybody (Backstreet’s Back)” (No. 4, Hot 100)
By 1998, Backstreet Boys weren’t alone; *NSYNC was rising. But with “Everybody,” they were original, and “sex-u-aaaal,” thanks to the synth bass cooked up by Max Martin and Denniz Pop. (Nick Carter was only 17 singing about body-rockin’). Initially excluded from their US debut, the stomping track’s fusion of European pop, R&B, and stadium-rock choruses became the Cheiron Studios sound, proving a perfect introduction – alright! – N.F.
7. OutKast, “Rosa Parks” (No. 55, Hot 100)
Atlanta’s hip-hop hub status was known by the late 90s. Big Boi and Andre, prepping their third album, had hits and were three years past being booed at the Source Awards. By Aquemini, both had much to say. Years before their split, they created Aquemini, a funky, spaced-out triumph. “Rosa Parks” became its biggest hit. Big Boi’s hook and verse meld with Andre’s gypsy tale, and Andre’s stepfather’s harmonica solo seals the deal. Even Rosa Parks herself eventually approved. – C.P.
6. The Verve, “Bitter Sweet Symphony” (No. 12, Hot 100)
“Bitter Sweet Symphony” feels like slow motion, with strings and Richard Ashcroft’s melancholy voice. The music video and its use in Cruel Intentions are unforgettable. Sampling an orchestral version of Rolling Stones’ “Last Time,” proved costly for The Verve, but resulted in the best song Mick Jagger and Keith Richards have “written” in 30 years. – D.W.
5. Brandy & Monica, “The Boy Is Mine” (No. 1, Hot 100)
Brandy and Monica, both successful artists, reached new heights with “The Boy Is Mine.” The Rodney “Darkchild” Jenkins duet featured the divas battling over a two-timing man. Mint vocals, timeless production, and attitude created a perfect storm. “The Boy Is Mine” became their first No. 1, spending 13 weeks at the top, becoming a revered song in both catalogs despite rumored rivalry. – S.J.H.
4. *NSYNC, “Tearin’ Up My Heart” (No. 59, Hot 100)
Despite a lack of boy bands in 2018, 1998 had countless teenage heartthrobs vying for pop supremacy. *NSYNC surged with their US debut, making the world dance to “I Want You Back” and “Tearin’ Up My Heart.” The latter, the album opener, remains undeniable. Agonizing love never sounded so good. Stay? Work it out? Or dance to blissful pop and worry about drama later? – C.L.
3. Natalie Imbruglia, “Torn” (No. 42, Hot 100)
Every year, an article reveals the “shocking truth”: Natalie Imbruglia’s “Torn” is a cover. Originally by Ednaswap in 1993, released in Danish by Lis Sorensen, then by Ednaswap again, it found little success until Imbruglia’s version. The story is well-circulated, yet each exposé feels like breaking news. Because Imbruglia’s “Torn” feels undeniably hers. Her pacing, from panicked to distraught, feels too lived-in to be borrowed. Every moment, from intro to outro, is exquisite ruination, recently interpolated by Brockhampton. Imbruglia couldn’t replicate its success, but capturing magic once is tough to recapture. Wait, “Torn” was a cover? Damn. – A.U.
2. Lauryn Hill, “Doo Wop (That Thing!)” (No. 1, Hot 100)
“Doo Wop (That Thing!)” was inescapable in late 1998, warning about being used “for that thing.” Lauryn Hill, already known from The Fugees, achieved solo superstardom with this track. “Which samples” 5th Dimension’s “Together Let’s Find Love,” “Doo Wop” earned Hill her first No. 1, making her one of few female rappers to top the chart solo. It also won Grammys and MTV VMAs, including Video of the Year, making her the first MC to win the top honor. Beyond accolades, “Doo Wop” is egalitarian, advising both sexes without pitting them against each other. Ahead of her time, Hill proved rap could unite and empower. – T.C.
1. Aaliyah, “Are You That Somebody?” (No. 21, Hot 100)
“Are You That Somebody?” is currently inaccessible on streaming platforms due to rights issues. It remains elusive, like something to be chased. From the past – 20 years ago – yet sounding futuristic. Produced and written by Timbaland and Static Major, sung by Aaliyah, it was created like a dream. Timbaland received a 4 a.m. call for a Dr. Doolittle soundtrack hit by 8 a.m. Eddie Murphy and talking animals hardly mattered – the payday beckoned. Timbaland, Aaliyah, and Static created magic. Before the baby sample, the staccato bass and drums create empty pockets in the beat, like dodging raindrops. The clucking and popping are Timbaland’s mouth tap-dancing. Aaliyah’s vocals create sound bubbles. Lyrics describe love as a secret. At 53 seconds, the baby sample drops, unexpected and awe-inspiring. Prince used the same sample in 1982, but the chutzpah to let it coo repeatedly through this skeletal beat is unique. Grammy-winning producer Bryan-Michael Cox told Vibe in 2008, “It ain’t been a record like that since.” Drake interpolated Static’s hook for Young Money’s “BedRock,” and James Blake sampled Aaliyah’s voice for “CMYK.” Sasha Frere-Jones wrote in The New Yorker, it’s “still effervescing.” Ten out of ten agree: this is not regular. “Are You That Somebody?” persists in cultural memory despite being unavailable for purchase or streaming. Millions know the 1969 baby sample by heart. Aaliyah passed in 2001. “Somebody” remains sacred territory, hidden in plain sight, accessible only to Aaliyah and Timbaland. – R.S.
