The year 1999 stands as a monumental chapter in popular music history, a time when genres blurred, new stars emerged, and the industry reached a commercial peak. It was a year brimming with musical innovation and unforgettable hits, a soundtrack to the anxieties and excitements of the impending millennium. To truly capture the essence of this vibrant period, we delve into 99 songs from 1999 that not only topped charts but also shaped the cultural landscape.
This wasn’t just another year in music; it was a cultural explosion. Pop music in 1999 was a melting pot of genres, styles, and personalities, pushing boundaries and setting trends that resonate even today. From breakthrough artists to seasoned veterans reinventing themselves, the sheer volume of impactful music released in those 12 months is staggering. The industry was booming, with record sales reaching such heights that the Recording Industry Association of America (RIAA) had to introduce a new certification level to acknowledge the blockbuster albums and singles dominating the airwaves. This era of mega-pop was so star-studded that deciphering the hierarchy of hits felt like a task only Carson Daly himself could manage.
This list, far from being exhaustive, aims to highlight 99 standout tracks that encapsulate the spirit of 1999. It celebrates the era’s defining sounds, from the last gasps of grunge influence to the burgeoning sounds of nu-metal and teen pop, and the continued dominance of R&B and hip-hop. Eligibility for this list includes songs released as singles in 1999 or those that first charted on Billboard in 1999, capturing the year’s musical zeitgeist. While some hits that technically broke through in early 2000 are earmarked for next year’s consideration, this collection focuses squarely on the sounds that permeated the airwaves as the 20th century drew to a close.
So, join us as we journey back to 1999, exploring 99 songs that represent the pinnacle of turn-of-the-millennium megapop. Get ready to revisit the tracks that soundtracked your year, and perhaps discover some gems you might have missed. From heartfelt ballads to high-energy anthems, these 1999 Songs are a testament to a truly remarkable year in music.
99. Sarah McLachlan, “I Will Remember You” (Live)
Sarah McLachlan’s “I Will Remember You” is a timeless piano ballad that perfectly encapsulates the bittersweet feeling of farewells and moving on. Originally released years prior, this live version from her Mirrorball album became a surprise hit in 1999, resonating deeply with audiences. Its gentle melody and poignant lyrics evoke images of montages and emotional goodbyes, making it a staple for significant life events, from graduations to memorials. The song’s enduring appeal lies in its universal message of remembrance and cherishing moments past, ironically transforming it into an ode to itself.
98. Maxwell, “Fortunate”
Alt text: Close-up portrait of neo-soul artist Maxwell in 1999, showcasing his sophisticated and soulful image.
“Fortunate” by Maxwell is a smooth, quiet storm jam that showcases his signature neo-soul style. Initially, songwriter R. Kelly convinced Maxwell to choose this track over another for the Life soundtrack, a decision that proved fruitful. After his sophomore album Embrya left some fans seeking direction, “Fortunate” grounded Maxwell’s musical journey. His soaring falsetto immediately captivates, enveloping listeners in a lush, intimate vocal performance. The song’s power lies in its simple yet profound one-word title, “Fortunate,” perfectly capturing the mood Maxwell creates, distinguishing it from countless other songs about being “blessed” or “lucky.”
97. Limp Bizkit, “Nookie”
The nu-metal era of the late 90s and early 2000s was undeniably a unique and often polarizing period in music history. Limp Bizkit’s “Nookie” emerged as one of its defining tracks, a smash hit that cleared away the remnants of grunge. From their album Significant Other, “Nookie” featured frontman Fred Durst’s confrontational and misogynistic lyrics, set against an undeniably catchy and aggressive groove. While the song’s chauvinistic themes remain a point of contention, its raw energy and angsty appeal cemented Limp Bizkit’s place in the 1999 musical landscape.
96. Blur, “Coffee & TV”
Alt text: Group portrait of British band Blur in 1999, featuring Graham Coxon, Damon Albarn, Alex James, and Dave Rowntree, highlighting their Britpop era style.
After their grunge-infused hit “Song 2,” Blur shifted gears with “Coffee & TV,” a mid-tempo, charmingly precious track. Sounding almost Belle & Sebastian-esque, the song explored the soul-crushing banality of a quiet life, reflective of guitarist Graham Coxon’s newfound sobriety, who took lead vocals on this track. Despite its thematic focus, its infectious melody became a hit, further amplified by its memorable music video featuring a milk carton character on an odyssey, even captivating characters like A.J. Soprano.
95. S Club 7, “S Club Party”
S Club 7 performing at Power In The Park concert 1999, Southampton, Britain.
Alt text: S Club 7 performing live at Power In The Park concert in Southampton, Britain in June 1999, capturing their energetic pop performance.
S Club 7, the seven-member British pop group, ensured their lasting memory with “S Club Party.” This high-energy track not only gets any party started but also serves as a perfect introduction to the group itself. While lyrics heavily referencing “S Club” and individual member shout-outs could be seen as self-indulgent, the undeniably catchy melodies and singalong chants made “S Club Party” a convincing anthem in 1999, asserting that there really “ain’t no party like an S Club party.”
94. Foxy Brown, “Hot Spot”
“Hot Spot” by Foxy Brown, despite its modest chart performance, remains a powerful and impactful track from her Billboard 200-topping album Chyna Doll. Co-written with Jay-Z, the song boasts braggadocious lyrics like “My coat is ostrich, flow is the hottest,” set to a sharp, scratchy beat produced by Irv Gotti and Lil Rob. Following collaborations with major artists on previous singles, “Hot Spot” was Foxy Brown’s first solo lead single. With the chorus declaration, “This is our world, me and my girls,” the track transforms into a fierce ladies’ night anthem, celebrating female empowerment.
93. The Get Up Kids, “Ten Minutes”
Alt text: The Get Up Kids band portrait from 1999 featuring band members Matt Pryor, James Dewees, Jim Suptic, Ryan Pope, and Rob Pope, showcasing their emo band image.
In 1999, emo was on the cusp of mainstream breakthrough, and The Get Up Kids were at the forefront. Their album Something To Write Home About and its centerpiece, “Ten Minutes,” became pivotal in the genre’s rise. Originally recorded in a scrappier version, the album version of “Ten Minutes” featured new keyboardist James Dewees, whose swirling synthesizers amplified co-frontman Jim Suptic’s emotionally charged choruses, elevating the song to power-pop glory. The song captured the raw emotion and melodic sensibility that defined late 90s emo.
92. Dead Prez, “Hip Hop”
Immortalized as the intro music for Chappelle’s Show, Dead Prez’s “Hip Hop” has aged into a timeless track. Contrary to being solely a bitter critique, the song offers a magnanimous perspective from MCs Stic.man and M-1. M-1’s verse promotes honesty, trusting listeners to discern truth from falsehood in hip-hop, while Stic.man’s final lines emphasize the ongoing struggle for authenticity and social justice within the genre. The track’s enduring relevance highlights the persistent issues within hip-hop and society at large, particularly Stic.man’s poignant closing, “This real hip-hop, and it don’t stop ’til we get the po-po off the block.”
91. Brandy, “Almost Doesn’t Count”
Brandy portrait 1999, Brandy Norwood in an elegant pose.
Alt text: Elegant portrait of R&B singer Brandy Norwood in 1999, highlighting her poised and sophisticated image during her Never Say Never era.
Following her massive hits “The Boy Is Mine” and “Have You Ever,” Brandy delivered “Almost Doesn’t Count” in spring 1999. This fifth single from Never Say Never presented a more nuanced perspective on failed relationships. While heartbroken by her ex’s “funny hesitation,” Brandy’s laid-back vocals and repetitive lyrics over solemn guitar strumming convey a mature wisdom, choosing to walk away from half-hearted promises. The song showcased Brandy’s growth as an artist, moving beyond youthful heartbreak to a more reflective and discerning perspective on love.
90. No Doubt, “New”
No Doubt’s “New,” featured in the cult classic film Go, signaled both an alt-rock hit and a stylistic evolution for the band. This standalone single bridged the gap between Tragic Kingdom and Return to Saturn. Like classic No Doubt, it features Gwen Stefani’s powerful vocals and a catchy chorus, but “New” introduced synth-heavy instrumentation, hinting at the new wave experimentation that would define their next album and beyond, particularly songs like “Simple Kind of Life.” “New” wasn’t just a song; it was a harbinger of No Doubt’s future sound.
89. 112 feat. Lil Zane, “Anywhere”
“Anywhere” by 112 featuring Lil Zane is a late-90s R&B track that immediately grabs attention with its unmistakable opening note, promising sensuality and playfulness. The silky-smooth vocals of Slim and Q deliver on this promise, making even outdated suggestions like a waterbed scenario sound enticing. “Anywhere” became an anthem for spontaneous romance, capturing the mood of late-night desires and impulsive passion, solidifying 112’s status in the R&B landscape of 1999.
88. B*Witched, “C’est La Vie”
Alt text: BWitched group portrait from 1999, featuring Irish girl group members Edele Lynch, Lindsay Armaou, Sinéad O’Carroll, and Keavy Lynch, highlighting their youthful pop image.*
B*Witched’s “C’est La Vie” opens with playful banter before diving into surprisingly suggestive lyrics. The Irish quartet, all credited as songwriters, seemed to take the Spice Girls’ innuendo-laden songs as a challenge. Lines like “I’ll show you mine if you show me yours” are juxtaposed with a breezy, nursery rhyme-like chorus, creating a duality that made the song enduringly catchy. The thrill of subtle naughtiness hidden within a seemingly innocent pop song is a key element of “C’est La Vie”‘s lasting appeal.
87. Aimee Mann, “Save Me”
After ‘Til Tuesday, Aimee Mann carved a successful solo career as a singer-songwriter, earning critical acclaim and catching the attention of director Paul Thomas Anderson. Anderson used Mann’s music in Magnolia, for which she wrote “Save Me.” This dryly humorous yet sincere plea for a savior, with lines like “You look like a perfect fit/ For a girl in need of a tourniquet,” showcases Mann’s poignant songwriting. Her simple request for salvation, delivered with understated emotion over acoustic guitar, carries a weight that resonates deeply.
86. Kenny Chesney, “She Thinks My Tractor’s Sexy”
Alt text: Kenny Chesney performing live on stage in 1999, playing an acoustic guitar and engaging with the audience during a country music concert.
Kenny Chesney’s “She Thinks My Tractor’s Sexy” significantly altered the course of country music. Preceding “bro-country,” this song humorously touted the allure of farm equipment. While it paved the way for artists like Florida Georgia Line and Luke Bryan, Chesney’s approach in 1999 was more laid-back and winking, never anticipating it would become a dominant genre ethos. The song’s playful take on rural charm and attraction resonated with audiences, marking a turning point in country music’s thematic direction.
85. Filter, “Take a Picture”
Filter, known for their hard-rocking “Hey Man, Nice Shot,” surprised listeners with “Take a Picture.” While their album Title of Record started with the alt-metal track “Welcome to the Fold,” it was “Take a Picture,” a dreamy, introspective song about drunken airplane antics, that became their crossover hit. Its acoustic chug and singalong chorus, “Could you take my picture/ ‘Cause I won’t remember,” resonated with a broader audience, while its shouted climax, “HEY DAD, WHADDYA THINK ABOUT YOUR SON NOW??,” retained the band’s raw edge.
84. Busta Rhymes, “Gimme Some More”
Sampling the unsettling strings from Bernard Herrmann’s “Prelude (Psycho Theme),” Busta Rhymes’ “Gimme Some More” creates an atmosphere of suspense and frenetic energy. Busta’s rapid-fire, voluble rasp takes off at breakneck speed over the stuttering beat. The song maintains a perpetual tension, never quite reaching the fever pitch it promises, leaving listeners on edge, much like Janet Leigh in Psycho, constantly anticipating the next unexpected turn.
83. Marc Anthony, “I Need to Know”
Alt text: Marc Anthony performing passionately on stage in 1999, singing into a microphone during a live concert, capturing his energetic stage presence.
Marc Anthony’s “I Need to Know” perfectly bridges American and Latin pop, achieving success in both English and Spanish as “Dímelo.” While its repeated references to “baby girl” may be outdated by today’s standards, the song’s punchy, percussive rhythm and Anthony’s passionate delivery made it a smash. Its simplicity, with the title phrase repeated over 30 times, emphasizes the directness of desire and the urgency of needing to know, contributing to its broad appeal.
82. Orgy, “Blue Monday”
Orgy’s industrial-rock cover of New Order’s “Blue Monday” stands out as a successful reimagining of a classic. By replacing the original’s four-on-the-floor beat with crushing guitars, Orgy highlighted the song’s inherent angst. The lyric “How does it feel, to treat me like you do?” transforms from a lament into an angry howl, giving a new, harder edge to the synth-pop classic. While New Order’s version remains definitive, Orgy’s rendition offered a powerful and relevant reinterpretation.
81. *NSYNC, “I Drive Myself Crazy”
NSYNC group portrait 1999, Justin Timberlake, JC Chasez, Chris Kirkpatrick, Joey Fatone, Lance Bass.
Alt text: NSYNC group portrait from 1999, featuring boy band members Justin Timberlake, JC Chasez, Chris Kirkpatrick, Joey Fatone, and Lance Bass, showcasing their late 90s pop star image.
“I Drive Myself Crazy,” the final single from *NSYNC’s debut album, is their most easy-listening track. Featuring Chris Kirkpatrick on lead vocals, this quasi-power ballad, though not a chart-topper, became a TRL staple. Its music video, featuring Clueless‘ Elisa Donovan, captured late 90s pop culture. While the video’s mental health parody is questionable today, the song’s melodic appeal and relatable themes of romantic frustration have ensured its lasting popularity.
80. Armand Van Helden feat. Duane Harden, “You Don’t Know Me”
“You Don’t Know Me” by Armand Van Helden featuring Duane Harden is a dance music Frankenstein, combining sampled 70s disco strings, early 90s house drums, and Duane Harden’s powerful vocals. This potent combination reached No. 2 on the Dance Club Songs chart and topped the UK charts, even dethroning The Offspring’s “Pretty Fly (For a White Guy).” The track’s eclectic mix of samples and driving beat made it a standout dance anthem of 1999.
79. B.G. feat. Baby, Turk, Mannie Fresh, Juvenile & Lil Wayne, “Bling Bling”
Before Lil Wayne became a rap superstar, he and Cash Money Records introduced “Bling Bling” into the cultural lexicon. Driven by a chirping Mannie Fresh beat, “Bling Bling” became a top 40 hit and a cultural phenomenon. The song’s video, led by B.G., showcased countless ways to flaunt wealth, and the term “bling bling” permeated commercials, movies, and everyday language. Though the phrase’s novelty has faded, the song’s flashy energy remains undeniable.
78. Ginuwine, “So Anxious”
Alt text: Ginuwine performing live on stage in 1999, wearing a black leather outfit and singing into a microphone, showcasing his R&B stage presence.
Despite its title, Ginuwine’s “So Anxious” is anything but shy. With Static Major’s songwriting and Timbaland’s production, the track was destined for success, but Ginuwine’s vocal performance, particularly his honey-dripped falsetto on the extended “soooooo anxious,” elevates it. While not as groundbreaking as “Pony,” “So Anxious” delivers everything loved about grown-and-sexy R&B, solidifying Ginuwine’s status as a genre mainstay.
77. Donell Jones feat. Lisa “Left Eye” Lopes, “U Know What’s Up”
Donell Jones’s “U Know What’s Up” featuring Lisa “Left Eye” Lopes is a smooth ode to sundresses and summer vibes. Evoking images of summer days, chromed-out Hummers, and exposed thighs, the song’s sticky hook and Eddie F. and Darren Light’s production create an irresistible groove. Left Eye’s verse adds a playful edge, making “U Know What’s Up” a quintessential late 90s R&B summer anthem, celebrating carefree days and romantic attraction.
76. System of a Down, “Sugar”
System of a Down band portrait 1999, Serj Tankian, Daron Malakian, Shavo Odadjian, John Dolmayan.
Alt text: System of a Down band portrait from 1999, featuring Serj Tankian, Daron Malakian, Shavo Odadjian, and John Dolmayan, capturing their nu-metal band image.
System of a Down’s debut single “Sugar” was the perfect introduction to their raw energy and unique sound. Capturing their chaotic live performances, the song showcased their DNA: pummeling riffs, shifts between singing and screaming, and abrupt tempo changes, all within two and a half minutes. At the dawn of nu-metal’s mainstream reign, “Sugar” demonstrated the genre’s versatility and System of a Down’s distinctive approach.
75. D’Angelo feat. Method Man and Redman, “Left and Right”
The collaboration between D’Angelo and hip-hop duo Method Man and Redman on “Left and Right” seemed unlikely on paper, but resulted in effortless virtuosity. The Voodoo single eases in with smooth chemistry, all three vocalists playing off each other. The track’s laid-back groove and seamless blend of R&B and hip-hop sensibilities highlight the artists’ collective talent and improvisational feel.
74. Monica, “Angel of Mine”
Monica’s “Angel of Mine,” originally a hit for UK girl group Eternal, found even greater success stateside, becoming her third Hot 100 No. 1. This endearing love song, with its sighing lyrics and mid-tempo rhythm, resonated deeply with young lovebirds. Monica’s winning performance and the song’s simple yet profound lyrics, such as “I look at you, looking at me/ Now I know why they say the best things are free,” contributed to its widespread appeal and enduring charm.
73. Mobb Deep feat. Lil Kim, “Quiet Storm” (Remix)
Alt text: Mobb Deep group portrait from 1999, featuring hip-hop duo Prodigy and Havoc, highlighting their hardcore rap image.
Mobb Deep’s “Quiet Storm” remix featuring Lil Kim flipped the quiet storm concept into a chilling club anthem. Sampling a bassline from Grandmaster Flash, and featuring an immaculate verse from Lil Kim, the remix set a precedent for rappers mixing club vibes with somber reflection. Lil Kim’s verse and the track’s dark, atmospheric production solidified its status as a unique and influential hip-hop track.
72. 702, “Where My Girls At”
702’s “Where My Girls At,” penned by Missy Elliott, became a standout ladies’ anthem of the late 90s, alongside classics by Destiny’s Child and TLC. Despite verses less commanding than those megahits, “Girls” boasts an infectious chorus that instantly grabs attention. Its empowering message and catchy hook made it a staple girls’ night out anthem, solidifying 702’s place in the era’s girl group landscape.
71. Rage Against the Machine, “Guerrilla Radio”
Alt text: Rage Against the Machine performing live on stage in 1999, featuring Zack de la Rocha, Tom Morello, Tim Commerford, and Brad Wilk, capturing their energetic and politically charged performance.
Rage Against the Machine’s “Guerrilla Radio” became a scorching call to arms. Adopted by gamers through Tony Hawk’s Pro Skater 2 and awarded a Grammy, its adrenaline-pumping energy resonated widely. The song’s fusion of funk-metal with politically charged lyrics made it both a critical and commercial success, solidifying Rage Against the Machine’s impact on music and activism.
70. H.O.T., “I Yah!”
H.O.T.’s 1999 hit “I Yah!” is considered a landmark in K-pop history. Fueled by rage and grief, the song blends smooth orchestral elements with dramatic metal and hard rock influences, including wailing guitar riffs and screaming vocals. Inspired by a tragic fire caused by corruption, “I Yah!” became an anthem for youth frustration and a call against societal corruption, reflecting H.O.T.’s role as socially conscious K-pop pioneers.
69. Moby, “Bodyrock”
Alt text: Moby performing a live DJ set in 1999, showcasing his electronic music artistry and stage presence during a concert.
“Bodyrock” from Moby’s Play captures his genius as a dance artist. With Gang of Four-inspired guitar riffs and Spoonie Gee samples, the track delivers euphoric release. Despite initial Fatboy Slim comparisons, “Bodyrock” achieves a unique ecstatic energy. Its music video embodies its spirit, encouraging listeners to embrace freedom and uninhibited expression on the dance floor.
68. Black Star feat. Common, “Respiration”
Black Star’s “Respiration” featuring Common, from their album Mos Def and Talib Kweli Are Black Star, is a tribute to the relentless spirit of New York City. Released in 1998, it charted in 1999, paying homage to the city’s grit while grappling with its influence. “Respiration” remains Black Star’s last single, but its impact as a poetic and socially conscious hip-hop track endures, with lingering hopes for future music from the duo.
67. TLC, “Unpretty”
TLC group portrait 1999, T-Boz, Left Eye, Chilli posing in studio.
Alt text: TLC group portrait from 1999, featuring T-Boz, Left Eye, and Chilli posing in a studio, highlighting their iconic 90s girl group style.
TLC’s “Unpretty” from FanMail continued their legacy as an empowering girl group. This alt-rock-influenced track, their second straight Hot 100 No. 1, tackles insecurities and promotes self-worth. Twenty years later, “Unpretty” remains relevant, emphasizing that true beauty comes from within, beyond superficial standards. Its message of self-love and acceptance resonates across generations.
66. Wilco, “A Shot in the Arm”
Wilco’s “A Shot in the Arm,” from Jeff Tweedy, is a drug-themed song with clever, evocative lyrics like “The ashtray says you’ve been up all night.” Driven by repetition, like an addiction, the song builds to a powerful climax as Tweedy embraces his fix, synths dissonant, shouting “something in my veins, bloodier than blood.” The harrowing comedown, with the line “What you once were isn’t what you want to be any more,” adds depth to this raw, unflinching portrayal of addiction.
65. Garbage, “Special”
Garbage’s “Special,” led by Shirley Manson’s lethal pen, dismantles unrequited love with directness. Lyrics like “Now you’re here and begging for a chance/ There’s no way in hell I’d take you back” are delivered over Butch Vig’s electronic-influenced production and Manson’s harmonies. Borrowing a lament from Chrissie Hynde, “Special” secured Garbage’s enduring place in music, showcasing Manson’s fierce persona and the band’s innovative sound.
64. Phil Collins, “You’ll Be in My Heart”
Alt text: Phil Collins performing live on stage in 1999, singing into a microphone during a concert, highlighting his iconic singing style.
Phil Collins’ “You’ll Be in My Heart,” from the Tarzan soundtrack, became another chart-topping success for the legendary artist. Collins’ memorable performance transforms what could have been cheesy into a heartfelt lullaby, solidifying its status as a top Disney song. Winning an Oscar, Golden Globe, and a Super Bowl halftime gig, “You’ll Be in My Heart” underscored Collins’ enduring musical talent and cross-generational appeal.
63. Kelis, “Caught Out There”
Kelis’ debut single “Caught Out There” made a strong, visceral impact in 1999. Her raw, bilious chorus and The Neptunes’ explosive beat created a domestic drama turned anthem. The track’s blend of raw emotion and futuristic production signaled Kelis and Pharrell Williams as potential rivals to Missy Elliott and Timbaland, promising a dynamic future in music.
62. Jamiroquai, “Canned Heat”
Alt text: Jamiroquai frontman Jay Kay performing energetically on stage in 1999, dancing and singing during a live concert, showcasing his dynamic stage presence.
Jamiroquai’s “Canned Heat,” with its jazzy intro and striking bass groove, vibrated through a period of global political turmoil. Jay Kay’s focus on the boogie and dancing through chaos resulted in a dance club hit reminiscent of disco’s peak. “Canned Heat” offered escapism and pure musical energy, becoming a dance floor staple in 1999.
61. Fastball, “Out of My Head”
Fastball’s “Out of My Head” features an iconic organ moment and an unusual structure, largely consisting of its chorus repeated without traditional verses. This unconventional approach worked, making it a slow-burning top 40 hit. Its catchy chorus and unique structure were so effective that Machine Gun Kelly and Camila Cabello interpolated it in their hit “Bad Things” in 2017, demonstrating its lasting melodic appeal.
60. Vengaboys, “Boom Boom Boom Boom”
Alt text: Vengaboys group portrait from 1999, featuring Denise Post-Van Rijswijk, Robin Pors, Roy den Burger, and Yorick Bakker in colorful and playful outfits, highlighting their Eurodance group image.
Vengaboys’ “Boom Boom Boom Boom” is a euphoric Eurodance anthem. Despite seemingly childlike lyrics, its synth melodies and chord progression evoke a complex mix of joy and underlying melancholy. The song’s simple yet effective structure and high-energy beat made it a club hit, demonstrating that even seemingly cheesy Eurodance can create complex emotional responses.
59. Lauryn Hill, “Everything Is Everything”
Lauryn Hill blurred genre lines in the late 90s, excelling as both rapper and singer, as showcased in “Everything Is Everything.” Her verses address injustice and inner-city struggles, while her soothing vocals on the chorus offer hope and change. Hill’s elastic flow as an MC and her powerful message made “Everything Is Everything” a standout track, solidifying her multifaceted talent.
58. Sugar Ray, “Every Morning”
Sugar Ray performing on The Tonight Show with Jay Leno in 1999, Mark McGrath in lead vocals.
Alt text: Sugar Ray performing on The Tonight Show with Jay Leno in 1999, featuring Mark McGrath singing lead vocals, capturing their pop-rock band performance.
Sugar Ray’s “Every Morning” cleverly masked raunchy lyrics with irresistible hooks. Its upbeat riff and catchy melody made the opening line, “Every morning there’s a halo hanging from the corner of my girlfriend’s four-post bed,” deceptively fun to sing. Whether listeners grasped the song’s suggestive themes or not, its playful melody propelled it to No. 3 on the Hot 100, cementing Sugar Ray as sly pop innovators.
57. Brad Paisley, “He Didn’t Have to Be”
Brad Paisley’s earnest performance of “He Didn’t Have to Be” sells its heartfelt story of a stepfather’s bond with his stepson. Co-written by Kelley Lovelace, the song became Paisley’s first of 19 country radio No. 1s. Its relatable narrative of growing familial love resonated deeply, making it one of Paisley’s most enduring and popular songs, especially among stepfamilies.
56. Creed, “Higher”
Alt text: Creed performing live on stage in 1999, featuring Scott Stapp singing lead vocals and Mark Tremonti playing guitar, capturing their rock band performance.
Creed’s “Higher” is defined by Scott Stapp’s soaring vocals and Mark Tremonti’s iconic guitar riff. The lead single from Human Clay, it epitomized Creed’s Christian-inspired blue-collar rock. Despite not being “cool,” their hits, particularly “Higher,” demonstrated the power of uninhibited rock anthems, resonating with a massive audience and achieving Diamond certification for the album.
55. Lil Wayne, “Tha Block Is Hot”
Lil Wayne was only 16 when he released “Tha Block Is Hot,” his debut single. Despite limited cursing on the album, the title track showcased his irrepressible confidence and charisma. His nimble flow over Mannie Fresh’s skittering beat and playful “tssssss!!” sizzle sound effects highlighted the young rapper’s burgeoning star power, foreshadowing his future superstardom.
54. Faith Hill, “Breathe”
Faith Hill’s “Breathe” solidified her crossover appeal with its sultry balladry. Her effortless vocal transitions from whisper to belt resonated on both pop and country radio. Spending six weeks atop Hot Country Songs and reaching No. 2 on the Hot 100, “Breathe”’s timeless quality and minimal production have made it a radio and karaoke staple.
53. Q-Tip, “Vivrant Thing”
Alt text: Q-Tip performing live on stage in 1999, rapping into a microphone during a concert, highlighting his hip-hop stage presence.
Q-Tip’s solo hit “Vivrant Thing” is a romantic tribute reminiscent of A Tribe Called Quest’s “Bonita Applebum.” Its airtight groove, slapping guitar, and hissing hi-hat create a funky, fresh sound. Q-Tip’s reverent lyrics about his girl’s conversational skills and intimate connection set “Vivrant Thing” apart as a genuinely appreciative and sensual hip-hop track.
52. Basement Jaxx, “Red Alert”
Basement Jaxx’s “Red Alert” is a dance floor classic with a monster hook. Its funky bassline builds tension before exploding into blissful 4/4 oblivion. Fluttering electro echoes, screaming synths, and a powerhouse vocal propelled this soulful house track to No. 1 on the Dance Club Songs chart, becoming a defining anthem of late 90s dance music.
51. Shania Twain, “That Don’t Impress Me Much”
Shania Twain portrait 1999, country-pop artist in stylish pose.
Alt text: Shania Twain portrait from 1999, showcasing her country-pop artist image with a stylish pose, during her Come On Over era.
Shania Twain’s “That Don’t Impress Me Much” remains culturally relevant decades later. Revealing the Brad Pitt reference origin in 2017 underscored its enduring legacy. The song’s pop-country sound foreshadowed Taylor Swift’s pop revolution a decade later. “That Don’t Impress Me Much” was a crossover hit, modeling a sound that would redefine pop-country.
50. Blink-182, “What’s My Age Again?”
Blink-182’s “What’s My Age Again?” is synonymous with its iconic music video featuring the band running naked through the streets. The anthem of immaturity, it defined Blink-182’s mission statement. Its pop-punk energy and lyrics celebrating youthful antics resonated widely, making it a defining track of late 90s pop-punk.
49. Fiona Apple, “Fast As You Can”
Fiona Apple stood apart from manufactured pop, establishing herself as a singular talent. “Fast As You Can” shattered any trace of youthful vulnerability. Lyrics hint at relationship highs and lows, while her moody vocals and the song’s spellbinding drums and percussion create a mature, intense atmosphere, showcasing Apple’s unique artistry.
48. Aphex Twin, “Windowlicker”
Alt text: Aphex Twin Windowlicker album art from 1999, showcasing abstract and surreal electronic music artwork, associated with experimental electronic music.
Aphex Twin’s “Windowlicker” parodied hip-hop music videos long before The Lonely Island. Its bizarre blend of slow-motion bikini-clad women and fundamentally weird dance music created a surreal and unforgettable visual and sonic experience. The track’s out-of-time quality, mixing noise, ambient, breakbeats, and turntable techniques, defied pop conventions, making it a unique and enduring piece of electronic music.
47. Backstreet Boys, “Larger Than Life”
Backstreet Boys’ “Larger Than Life” lived up to its title in 1999. From its expensive music video to AJ McLean’s opening scream and a guitar solo, it was an event. Millennium‘s way of ringing in the new era, “Larger Than Life” remains titanically catchy, with a chorus that no BSB song has surpassed, solidifying its status as a boy band anthem.
46. OutKast, “Da Art of Storytellin’ (Pt. 1)”
OutKast’s “Da Art of Storytellin’ (Pt. 1)” showcased Big Boi and André 3000’s lyrical prowess. Positioning hip-hop as storytelling, the duo traded tales over a hustling beat. Its multigenerational impact endures, from Watch the Throne samples to J. Cole homages, highlighting OutKast’s lasting influence on hip-hop narrative.
45. Hole, “Malibu”
Alt text: Hole band portrait from 1999, featuring Courtney Love, Eric Erlandson, Melissa Auf der Maur, and Samantha Maloney, showcasing their grunge-era rock band image.
Hole’s “Malibu” contrasted sharply with the snarling “Celebrity Skin.” Instead of Courtney Love’s wit and power chords, “Malibu” revealed a cathartic, grieving softness. Co-written with Eric Erlandson and Billy Corgan, it showcased a vulnerable side, earning a Grammy nomination and highlighting Hole’s range.
44. Brian McKnight, “Back at One”
Brian McKnight’s velvety vocals shine on “Back at One.” This heartfelt R&B ballad, penned solo by McKnight, promises enduring love, making women swoon. Covered by numerous artists and a wedding song staple, “Back at One”’s romantic sincerity and McKnight’s vocal delivery made it a lasting hit.
43. LFO, “Summer Girls”
Alt text: LFO group portrait from 1999, featuring boy band members Rich Cronin, Devin Lima, and Brad Fischetti in casual outfits, highlighting their late 90s boy band image.
LFO’s “Summer Girls” is an oddball love song referencing Paul Revere, New Kids on the Block, and Abercrombie & Fitch. Its random lyrics somehow convey a summer romance, while Rich Cronin’s rap-like delivery and pop culture references create a unique charm. Tied together by a catchy riff and record-scratching effect, “Summer Girls” proved that outlandish tunes can become timeless.
42. Mos Def, “Ms. Fat Booty”
Mos Def’s debut solo single “Ms. Fat Booty” samples Aretha Franklin, creating a timeless sound. Mos Def’s story of attraction feels surprisingly modern, portraying the titular woman as a “thirst trap” before social media terminology existed. The song’s twist ending and Mos Def’s smooth flow made it a standout hip-hop track.
41. Lit, “My Own Worst Enemy”
Alt text: Lit band portrait from 1999, featuring pop-punk band members A. Jay Popoff, Jeremy Popoff, Kevin Baldes, and Allen Shellenberger, showcasing their late 90s rock band image.
Lit’s “My Own Worst Enemy” is a pop-punk anthem defined by its opening guitar roar. Its repetitive riffs, sing-song melodies, and lyrics about youthful mistakes exemplified the pop-punk sound of 1999. The song’s universal message of drunken misadventures and catchy energy made it a lasting hit.
40. Lou Bega, “Mambo No. 5”
Lou Bega’s “Mambo No. 5” arrived perfectly in 1999, with its invigorating horns and danceable rhythm. A German artist reworking a Cuban song, its global appeal was undeniable. Even a Radio Disney edit with Disney characters broadened its reach. Despite legal issues over sampling, “Mambo No. 5” became a ubiquitous summer anthem with something for everyone.
39. Britney Spears, “(You Drive Me) Crazy” (The Stop Remix)
Britney Spears’ “(You Drive Me) Crazy” remix amplified the drama of “…Baby One More Time.” Featured on the Drive Me Crazy soundtrack, the remix transformed yearning into obsession. Spears’ re-recorded vocals, a new intro, and her “Stop!” interjection in the bridge made it a truly mind-blowing track.
38. Dixie Chicks, “Cowboy Take Me Away”
Alt text: Dixie Chicks group portrait from 1999, featuring Natalie Maines, Emily Strayer, and Martie Maguire in country outfits, showcasing their country music group image.
Dixie Chicks’ “Cowboy Take Me Away” held down the country fort with powerful harmonies and yearning fiddle. Expressing the melancholy of a different time, the song’s dream of love as salvation resonated deeply. Listening now, it reminds of their vocal power, before political controversies impacted their career.
37. Lee Jung Hyun, “Wa”
Lee Jung Hyun’s “Wa” marked a transformative moment in K-pop. Known as the Queen of Transformation, her shapeshifting performances were theatrical. “Wa” blended traditional instruments with pulsating beats, introducing techno to Korean pop. Her futuristic vision and performance artistry made “Wa” a first-generation K-pop classic.
36. KoRn, “Freak on a Leash”
KoRn’s “Freak on a Leash” is synonymous with its cinematic music video and MTV dominance. The song distills KoRn’s turn-of-the-millennium appeal: full choruses, twitchy guitar effects, Jonathan Davis’ creepy vocals, and nonsensical bridges. Defenders of nu-metal point to “Freak on a Leash”’s enduring energy as a prime example of the genre’s appeal.
35. Mandy Moore, “Candy”
Mandy Moore attending Billboard Music Awards 1999, teen pop artist in red dress.
Alt text: Mandy Moore attending the 1999 Billboard Music Awards in a red dress, showcasing her teen pop artist image during the Candy era.
Mandy Moore’s debut single “Candy” positioned her as the younger sister in teen pop. Compared to Britney and Christina, her sugary-pop sound was tween-focused. Despite modest chart peak, “Candy”’s shimmering sound, “missing you like candy” lyric, and spoken-word bridge made it addictive and unmissable.
34. Enrique Iglesias, “Bailamos”
Enrique Iglesias’ “Bailamos” demonstrated pop music’s Latin industry dominance in 1999. This flamenco-infused anthem became irresistible, topping the Hot 100. Featured on the Wild Wild West soundtrack and his English-language debut, “Bailamos” marked Iglesias’ crossover success and enduring presence on pop and Latin radio.
33. Tal Bachman, “She’s So High”
Tal Bachman’s “She’s So High” is a buoyant pop-rock ode to an unattainable woman. References to Cleopatra and Aphrodite, a 90s music video, and the euphoric “hiiiiiiigh” chorus create a wholesome, earnest depiction of hopeless love, making it a one-hit wonder with lasting appeal.
32. The Roots feat. Erykah Badu, “You Got Me”
The Roots’ “You Got Me” featuring Erykah Badu, their only top 40 Hot 100 hit, told a dual-perspective relationship story. Its focus on commitment and consistency resonated with both their cult following and pop audiences. The song’s minor-key melody and drum-and-bass outro added depth, making it a standout love song of the era.
31. Madonna, “Beautiful Stranger”
Alt text: Madonna performing live on stage in 1999, showcasing her iconic pop star persona and stage presence during a concert performance.
Madonna’s “Beautiful Stranger” featured psychedelic accents, a new sound for her. Its 60s influences appealed to older fans, while younger listeners embraced its modern pop sensibility. Co-written with William Orbit for Austin Powers, it won a Grammy for best song for visual media, her only songwriting Grammy to date.
30. Eiffel 65, “Blue (Da Ba Dee)”
Eiffel 65’s “Blue (Da Ba Dee)” is the best song about a color from an Italian group with a French name. Dismissed as Eurocheese, its high camp vocal delivery and baby-talk lyrics became its charm. “Blue” is the absurd European dance-pop song to end all absurd European dance-pop songs, achieving iconic status through its sheer ridiculousness.
29. Björk, “All Is Full of Love”
Björk’s “All Is Full of Love” featured a sweet, unsettling music video with android Björk making out with another robot. Advanced CGI and a trip-hop beat, spine-tingling harps, and violins carried the song’s gently uplifting message of universal affection. The video and song combined for a uniquely moving and futuristic artistic statement.
28. Ol’ Dirty Bastard feat. Kelis, “Got Your Money”
Ol’ Dirty Bastard’s “Got Your Money” featuring Kelis showcased his unique and eccentric artistry. From literal opening verse to deranged flow, ODB’s one-of-a-kind style, combined with Kelis’ earworm hook, created a surreal world of excess and insanity, becoming his biggest crossover hit.
27. Sixpence None the Richer, “Kiss Me”
Sixpence None the Richer performing on The Tonight Show with Jay Leno in 1999, Leigh Nash singing lead vocals.
Alt text: Sixpence None the Richer performing on The Tonight Show with Jay Leno in 1999, featuring Leigh Nash singing lead vocals, showcasing their folk-pop band performance.
Sixpence None the Richer’s “Kiss Me” is mushy, cute, sweet, and vulnerable, perfectly capturing the feeling of falling in love. Its connection with Dawson’s Creek and teen movies cemented its place in pop culture. Spending 16 weeks in the Hot 100 top 10, “Kiss Me” became a wedding and romance staple, embodying the language of falling in love.
26. Mariah Carey feat. Jay-Z, “Heartbreaker”
Mariah Carey bridged pop and hip-hop in the 90s, and “Heartbreaker” featuring Jay-Z perfected this formula. Sampling Stacy Lattisaw, it blended Mariah’s vocals with Jay-Z’s rhymes. The expensive music video, featuring Mariah fighting her alter ego Bianca, became iconic. “Heartbreaker” solidified Mariah’s pop-hip-hop fusion and video artistry.
25. Celine Dion, “That’s the Way It Is”
Celine Dion’s “That’s the Way It Is” shifted from her high drama hits towards a pillowy, adult-contemporary sound. Released as a new single on a greatest hits compilation, it embraced corniness with self-affirming lyrics. Dion’s stellar vocal performance and the song’s message resonated, marking a blissful high note before her pop radio impact waned.
24. Red Hot Chili Peppers, “Scar Tissue”
Alt text: Red Hot Chili Peppers performing live on stage in 1999, featuring Anthony Kiedis, Flea, John Frusciante, and Chad Smith, capturing their funk-rock band performance.
Red Hot Chili Peppers’ “Scar Tissue” marked a comeback after motorcycle accidents and guitarist changes. Wistful lyrics, subtle motivation, and John Frusciante’s guitar solo defined this Grammy-winning hit. Anthony Kiedis described it as a “phoenix-rising-from-the-ashes vibe,” leading to the Californication album and RHCP’s superstar resurgence.
23. Jay-Z feat. Amil, “N—a What, N—a Who (Originator 99)”
Jay-Z and Timbaland’s musical relationship began with “N—a What, N—a Who (Originator 99).” Jay-Z returned to rapid-fire flow over Timbaland’s beat, which sounded like a race against time. The track’s frenetic energy and Jay-Z’s intense delivery paid homage to his and Jaz-O’s earlier collaboration, “The Originators.”
22. Whitney Houston, “It’s Not Right, But It’s OK”
Whitney Houston performing at Brit Awards 1999, pop diva singing live.
Alt text: Whitney Houston performing live at the 1999 Brit Awards, singing into a microphone and showcasing her pop diva stage presence during the performance.
Whitney Houston’s “It’s Not Right, But It’s OK” showcased a fierce persona. Scolding a cheating partner over a Darkchild beat, she declared, “There’s no more tears left here for you to see.” Her revamped look in the music video and powerful performance hinted at a fuller personality, leaving fans wondering what her career could have been had this been displayed from the start.
21. Smash Mouth, “All Star”
Smash Mouth’s “All Star” became a cultural phenomenon. Catchy verses and off-kilter lyrics made it immediately popular. Featured in Shrek in 2001, it experienced a meme-driven resurgence in 2017, highlighting its enduring appeal and meme-ability, driving it back onto charts years later.
20. DMX, “Ruff Ryders Anthem”
Alt text: DMX performing live on stage in 1999, rapping into a microphone during a concert, highlighting his raw and energetic hip-hop performance.
DMX’s “Ruff Ryders Anthem” was a rowdy hood banger. X’s persona and genius for anthems made him a game-changer. The song’s raw energy and call-to-action made it a staple at concerts and sporting events, elevating team morale and embodying late 90s hip-hop aggression.
19. Len, “Steal My Sunshine”
Len’s “Steal My Sunshine” became the song of summer 1999. Driven by a giddy sample from Andrea True Connection, it offered a breezy balm amidst Y2K anxieties. Its repeated piano-and-wood-block earworm and sibling interplay created a beach-day vibe, while lyrics, reportedly written after a rave, added to its quirky charm.
18. Fatboy Slim, “Praise You”
Fatboy Slim’s “Praise You” was elevated by its iconic music video featuring the Torrance Community Dance Group. Directed by Spike Jonze, the video’s goofy charm matched the song’s communal, piano-led jubilance. The song and video combined for an iconic four minutes of late-90s dance-pop, winning MTV Video Music Awards and Grammy nominations.
17. Missy Elliott feat. Nas, Eve & Q-Tip “Hot Boyz”
Alt text: Missy Elliott performing live on stage in 1999, rapping into a microphone during a concert, highlighting her innovative and energetic hip-hop performance.
Missy Elliott’s “Hot Boyz” remix featured Nas, Eve, and Q-Tip, showcasing Missy’s collaborative brilliance. Setting a Hot Rap Singles record, the posse remix brought out the best in her collaborators. Timbaland’s futuristic production and Missy’s sultry hook combined with vivid verses from guest rappers to create a hot hip-hop track.
16. Foo Fighters, “Learn to Fly”
Foo Fighters’ “Learn to Fly” is a triumph from its opening riff. Sunny, catchy, and poppy, it followed action-packed hits like “Everlong” and “My Hero.” Its chorus and bridge are gems, while the music video, featuring Dave Grohl as pilot and flight attendant, added comedy gold, making it a complete package of music and visual wit.
15. Destiny’s Child, “Bills, Bills, Bills”
Destiny’s Child’s “Bills, Bills, Bills” told off deadbeat men through playful R&B. Penned by Kevin “She’kspere” Briggs and Kandi Burruss, it hit No. 1 on the Hot 100. Beyoncé’s pre-solo shine, sassy lyrics, and harpsichord-synth sound defined this anthem against freeloaders, marking Destiny’s Child’s breakthrough.
14. Dr. Dre feat. Snoop Dogg, “Still D.R.E.”
Alt text: Dr. Dre and Snoop Dogg performing live on stage in 1999, rapping into microphones during a concert, highlighting their iconic West Coast hip-hop partnership.
Dr. Dre’s “Still D.R.E.” featuring Snoop Dogg marked his comeback with an iconic staccato piano hook. Co-written by Jay-Z, it weaved Dre’s accomplishments into an indisputable flex. Though Dre’s voice may not always dominate conversation, his enduring influence on hip-hop, cemented by this track, speaks for itself.
13. Ricky Martin, “Livin’ La Vida Loca”
Ricky Martin’s “Livin’ La Vida Loca” became a pop phenomenon in 1999. Despite questionable lyrics, its canned horns, surf-rock guitar, and Martin’s charm made it inescapable. Sparking a Latin-pop explosion, it turned Martin into a superstar. Its energy and infectious rhythm made it a lasting party anthem.
12. Shania Twain, “Man! I Feel Like a Woman”
Shania Twain’s “Man! I Feel Like a Woman” is an explosive anthem. Its six-note synth riff and Twain’s powerful vocals declare a woman’s prerogative to have fun. A four-minute romp of raised voices and short skirts, it sounds like it’s setting a new high score every time that synth hook goes off, embodying female empowerment and joy.
11. Christina Aguilera, “Genie in a Bottle”
Christina Aguilera’s “Genie in a Bottle” launched her career and set her apart from teen-pop peers. Its soulful sound, squelching beat, and self-respecting lyrics about early sexual encounters established Aguilera’s vocal prowess and mature themes, making it a defining debut single.
10. Eminem, “My Name Is”
Alt text: Eminem performing live on stage in 1999, rapping into a microphone during a concert, highlighting his provocative and raw hip-hop performance style.
Eminem’s “My Name Is” introduced his witty and controversial humor. Over Dr. Dre’s cartoonish sample, Slim Shady previewed his infamous elements: mother-bashing, misogynistic jokes, and pop culture mockery. Becoming a top 40 smash and Grammy-winning track, it signaled that Eminem’s unapologetically flippant formula would be his path to success.
9. Jennifer Lopez, “Waiting For Tonight”
Jennifer Lopez’s “Waiting For Tonight” from On the 6 stands out among her hits. Universal themes, infectious music, and a timeless chorus define this track. Oozing sex appeal with sultry vocals and a jungle-themed video, its guitar strums and pulsating beat perfectly complement lyrics of longing and breathless “ohhhhhh-ohhhh-ohhhs,” making it a timeless hit.
8. Blink-182, “All the Small Things”
Blink-182’s “All the Small Things” is a glistening pop moment, clowning on boy bands while being a boy band in their own right. Tom DeLonge wrote it about his girlfriend, and the video cast them as a snickering, skate park boy band. Producer Jerry Finn’s pop-punk polish and infectious “na-na, na-na’s” made it a pop-punk masterpiece.
7. Cher, “Believe”
Cher singing national anthem at Super Bowl XXXIII 1999, pop icon in concert.
Alt text: Cher singing the national anthem at Super Bowl XXXIII in 1999, showcasing her iconic pop star image and powerful vocal performance.
Cher’s “Believe” is famed for its Auto-Tune vocal effects, but its power goes beyond technology. Cher’s delivery of “believe” pierces the pleasure center, and her empowering lyrical changes transformed it from a whiny song to an “I Will Survive: Ibiza” anthem. Her musical reinvention and the song’s dance floor resonance made it a timeless hit.
6. Lauryn Hill, “Ex-Factor”
Lauryn Hill’s “Ex-Factor” is a compositional and performance masterpiece. Its opening line, “It could all be so simple/ But you’d rather make it hard,” encapsulates its pain, confusion, and misery. Hill’s voice and self-harmonizing create emotional depth, while the Wu-Tang Clan sample provides its backbone, making it a soul-bursting track that transcends simple elements.
5. Santana feat. Rob Thomas, “Smooth”
Santana’s “Smooth” featuring Rob Thomas became deeply embedded in pop culture. From its drum fill to Santana’s guitar licks and Rob Thomas’ growl, every element is iconic. Phrases like “Man, it’s a hot one” instantly evoke the song. Despite being remembered as “that Rob Thomas song,” Santana’s guitar genius shines, making it a multi-generational hit.
4. Juvenile feat. Mannie Fresh & Lil Wayne, “Back That Azz Up”
Juvenile’s “Back That Azz Up” featuring Mannie Fresh and Lil Wayne creates a social experience. Its 15-second string intro acts like an alarm clock, waking up any party. Mannie Fresh’s club DJ background and Juvenile’s simple yet effective lyrics, like “Girl you’re working with some ass,” make it a dance floor command. Breaking regional hip-hop barriers, its influence extends to post-regional styles and Drake’s Nola-inspired sound.
3. Backstreet Boys, “I Want It That Way”
Backstreet Boys’ “I Want It That Way” didn’t need chart validation to become their biggest hit. The plucking guitar intro transports 90s babies back to poster-plastered bedrooms. Its bombastic production, epic key changes, and singalong chorus “You are my fire/ The one desire” made it a pop staple. Despite baffling lyrics, its emotional resonance and pop perfection earned it a record of the year Grammy nomination.
2. TLC, “No Scrubs”
TLC’s “No Scrubs” is a public service announcement against freeloaders. Defining a “scrub” as a car-less, mom-living, non-child-supporting man, it became a sassy anthem. Kandi Burruss and Kevin “She’kespere” Briggs’ production combined acoustic guitar with a hip-hop beat for a timeless sound. Left Eye’s inimitable rap verse and the space-age music video further solidified its iconic status.
1. Britney Spears, “…Baby One More Time”
Britney Spears’ “…Baby One More Time” is not just a career-making song but a watershed moment in pop music. Minimalist yet maximalist, instantly memorable yet endlessly listenable, it’s a shotgun wedding between funk-pop and the Swedish music machine. Everything that shouldn’t work, tracks as dangerous, bold, and visionary. Spears’ calculated blend of teenage naïveté and Lolita charm, combined with Max Martin’s production, created a pop game-changer that continues to resonate 20 years later.
