As the 20th century drew to a close, music in 1999 felt like a sonic explosion, a year overflowing with creativity and innovation as artists pushed boundaries and genres blurred. It was a year of iconic debuts, triumphant comebacks, and unforgettable hits that continue to resonate today. Trying to capture the full breadth of 1999’s musical landscape in just a few songs would be an impossible task. However, we’ve curated a list of 99 standout tracks that exemplify the vibrant and diverse soundscape of that pivotal year, celebrating the era of turn-of-the-millennium megapop and the sheer star power that defined the charts. Welcome to a journey back to 1999, where we praise the songs that shaped a generation.
99. Sarah McLachlan, “I Will Remember You” (Live) (No. 14, Hot 100)
Sarah McLachlan’s timeless piano ballad, “I Will Remember You,” initially graced the Brothers McMullen soundtrack before finding new life on her live album, Mirrorball. This gently moving track perfectly encapsulates the bittersweet feeling of farewells and moving forward. Its lyrics resonate with anyone who has experienced a significant departure, making it a staple for milestone events and moments of transition. Over time, “I Will Remember You” has evolved into a poignant anthem of remembrance itself, its melody and message echoing across generations.
98. Maxwell, “Fortunate” (No. 4, Hot 100)
“Fortunate,” a smooth quiet storm jam penned by R. Kelly, became a defining track for Maxwell’s neo-soul artistry. Originally intended as the title track for the Life soundtrack, R. Kelly convinced Maxwell to record “Fortunate” instead, a decision that undoubtedly benefited music lovers everywhere. Following his debut Maxwell’s Urban Hang Suite, some felt his sophomore album Embrya lacked focus, but “Fortunate” quickly dispelled those notions. Maxwell’s soaring falsetto and lush vocal delivery create an intimate and enveloping atmosphere, perfectly capturing the mood of feeling truly “fortunate” in love.
97. Limp Bizkit, “Nookie” (No. 80, Hot 100)
The nu-metal explosion of the late 90s and early 2000s was undeniably a unique period in music history, and Limp Bizkit’s “Nookie” stands as a defining anthem of that era. Emerging from their album Significant Other, “Nookie” showcased frontman Fred Durst’s signature blend of angst and aggression, delivered with an undeniably catchy groove. While the song’s lyrical content might be considered controversial today, “Nookie” captured the raw energy and rebellious spirit of the time, marking a shift away from the grunge era and solidifying nu-metal’s place in the mainstream.
96. Blur, “Coffee & TV” (Did not chart)
Blur, known for their Britpop anthems, surprised listeners with the mellow and charming “Coffee & TV.” Following their American breakthrough with the grunge-infused hit “Song 2,” Blur showcased their versatility with this mid-tempo track. Guitarist Graham Coxon took lead vocals on “Coffee & TV,” delivering a song that explored themes of quiet suburban life and sobriety with a touch of British wit. Its infectious melody and endearing music video, featuring a lost milk carton, cemented “Coffee & TV” as a beloved Blur classic, even capturing the attention of pop culture figures like A.J. Soprano.
95. S Club 7, “S Club Party” (Did not chart)
S Club 7 posing at 'Power In The Park' concert in 1999S Club 7 poses at ‘Power In The Park’ concert on June 15, 1999 in Southampton, Britain. Brian Rasic/Getty Images
S Club 7, the British pop group born from a BBC television series, burst onto the scene with the energetic and self-referential “S Club Party.” This infectious track served as both a party starter and a catchy introduction to the seven members of the group. While the numerous S Club references and member shout-outs might seem overtly promotional, the undeniable melodies and singalong nature of “S Club Party” made it a convincing anthem. Twenty years later, the song’s playful energy still evokes the carefree spirit of late 90s pop.
94. Foxy Brown, “Hot Spot” (No. 91, Hot 100)
Foxy Brown’s “Hot Spot,” despite its lower chart position, remains a powerful and influential hip-hop track from 1999. Featured on her Billboard 200-topping album Chyna Doll, this song showcases Foxy Brown’s confident flow and lyrical prowess. Co-written with Jay-Z, “Hot Spot” delivers braggadocious lines over a sharp beat crafted by Irv Gotti and Lil Rob. After collaborating with major artists on previous singles, “Hot Spot” marked Foxy Brown’s first solo single, asserting her dominance in the rap scene and creating a fierce anthem for women everywhere.
93. The Get Up Kids, “Ten Minutes” (Did not chart)
The Get Up Kids’ “Ten Minutes” arrived at a pivotal moment for emo music, just before the genre broke into the mainstream. In 1999, emo was still largely underground, and The Get Up Kids were at the forefront of its burgeoning scene. “Ten Minutes,” from their seminal album Something to Write Home About, became an anthem for the introspective and emotionally charged sound that defined the genre. Keyboardist James Dewees’ addition to the band after the initial recording added a layer of swirling synths, elevating the song’s power-pop sensibilities and amplifying the raw emotion in Jim Suptic’s vocals.
92. Dead Prez, “Hip Hop” (No. 49, Rap Songs)
Dead Prez’s “Hip Hop” has become an enduring and resonant track, famously known as the intro music for Chappelle’s Show. This signature single from the Florida-New York duo offers a sharp commentary on the state of hip-hop and society. While often perceived as a purely critical song, “Hip Hop” actually presents a balanced perspective, urging honesty and accountability within the music industry and beyond. MCs Stic.man and M-1’s verses remain strikingly relevant today, particularly Stic.man’s poignant closing lines about staying vigilant until true change arrives.
91. Brandy, “Almost Doesn’t Count” (No. 16, Hot 100)
Brandy photographed in 1999Brandy photographed on Oct. 29, 1999. Matthew Rolston/UPN/Delivered by Online USA via Getty Images
Brandy, riding high from her previous chart-topping hits, delivered a nuanced take on heartbreak with “Almost Doesn’t Count.” Released as the fifth single from her blockbuster album Never Say Never, this song showcased Brandy’s maturity and vocal control. At just 20 years old, she conveyed a complex emotional landscape, capturing the pain of a relationship with someone emotionally unavailable. Her laid-back delivery and repetitive lyrics underscore a quiet wisdom, recognizing the futility of half-hearted promises and choosing to walk away.
90. No Doubt, “New” (No. 7, Alternative Songs)
No Doubt’s “New,” featured in the cult classic film Go, signaled a stylistic evolution for the ska-punk band. This standalone single bridged the gap between their breakthrough album Tragic Kingdom and their fourth album Return to Saturn. “New” retained the band’s signature energy with a powerful chorus delivered by Gwen Stefani, but it also introduced synth-laden instrumentation, hinting at the new wave experimentation that would define their future sound. “New” was not just a song title; it was a harbinger of No Doubt’s exciting musical direction in the years to come.
89. 112 feat. Lil Zane, “Anywhere” (No. 15, Hot 100)
112’s “Anywhere” is a quintessential late-90s R&B track, instantly recognizable from its opening note. This smooth and seductive song is an ode to romance on demand, wherever and whenever the mood strikes. The promise of something sexy and playful is palpable from the first beat, and the silky vocals of Slim and Q deliver on that promise. Even the somewhat dated reference to a waterbed scenario adds to the song’s nostalgic charm, solidifying its place as a classic bedroom jam.
88. B*Witched, “C’est La Vie” (No. 9, Hot 100)
B*Witched, the Irish girl group, surprised listeners with the deceptively playful “C’est La Vie.” The song’s quirky opening banter might seem nonsensical, but it sets the stage for a track loaded with surprising innuendo. The quartet, credited as songwriters, seemed to take inspiration from the Spice Girls’ subtle suggestive lyrics and amplify them. Lines like “I’ll show you mine if you show me yours” and “Do you play with the boys?” add a layer of cheeky double entendre to the breezy, nursery-rhyme chorus, making “C’est La Vie” an enduringly catchy and slightly mischievous pop song.
87. Aimee Mann, “Save Me” (Did not chart)
Aimee Mann, known for her introspective songwriting, gained a new wave of recognition with “Save Me,” featured in Paul Thomas Anderson’s film Magnolia. After her band ‘Til Tuesday’s success in the 80s, Mann established herself as a critically acclaimed solo artist, and Anderson’s use of her music in Magnolia introduced her to a wider audience. “Save Me” is a darkly humorous yet sincere plea for rescue, delivered with Mann’s signature dry wit and poignant vocals. Her simple request, “Can you save me? Come on and save me,” resonates with a powerful vulnerability, making it a standout track from the film and her catalog.
86. Kenny Chesney, “She Thinks My Tractor’s Sexy” (No. 74, Hot 100)
Kenny Chesney’s “She Thinks My Tractor’s Sexy” became a pivotal song in country music, paving the way for the “Bro Country” movement. Before the rise of Florida Georgia Line and Luke Bryan, Chesney’s track celebrated rural charm with a lighthearted and playful approach. While it became a precursor to the more overtly commercial and sometimes controversial “Bro Country” sound, “She Thinks My Tractor’s Sexy” in 1999 exuded a more laid-back and winking take on love and rural life, never anticipating the genre evolution it would inspire.
85. Filter, “Take a Picture” (No. 12, Hot 100)
Filter, initially known for their industrial rock sound with “Hey Man, Nice Shot,” surprised audiences with the introspective and melodic “Take a Picture.” While their album Title of Record started with the heavier alt-metal track “Welcome to the Fold,” “Take a Picture” proved to be the album’s secret weapon. This dreamy, acoustic-driven song about drunken airplane antics resonated with a wider audience, crossing over into top 40 radio. The song’s singalong chorus and unexpected shouted climax (“HEY DAD, WHADDYA THINK ABOUT YOUR SON NOW??”) showcased Filter’s dynamic range and songwriting depth.
84. Busta Rhymes, “Gimme Some More” (No. 24, R&B/Hip-Hop Songs)
Busta Rhymes’ “Gimme Some More” is a frenetic and innovative hip-hop track built around a sample from Bernard Herrmann’s “Prelude (Psycho Theme).” The disorienting strings from the Psycho theme create an unsettling atmosphere, perfectly complementing Busta Rhymes’ rapid-fire delivery. The stuttering beat and Busta’s inimitable rasp keep listeners on edge, mirroring the suspenseful tension of the sampled Hitchcock film. “Gimme Some More” is a testament to Busta Rhymes’ unique style and his ability to create captivating and unpredictable hip-hop.
83. Marc Anthony, “I Need to Know” (No. 3, Hot 100)
Marc Anthony’s “I Need to Know” successfully bridged the gap between American and Latin pop, becoming a hit in both English and Spanish (as “Dímelo”). This punchy and rhythmic track showcased Anthony’s crossover appeal and vocal power. While the repeated phrase “baby girl” might be considered somewhat dated by today’s standards, the song’s central theme of needing reassurance in a relationship is timeless. The sheer repetition of the title phrase, over 30 times, ensures that listeners clearly understand the song’s core message.
82. Orgy, “Blue Monday” (No. 56, Hot 100)
Orgy’s industrial rock cover of New Order’s “Blue Monday” is a prime example of a successful cover song that reinvents and reveals new dimensions of the original. While New Order’s original is a synth-pop classic, Orgy’s version injects heavy guitars and a raw energy, transforming the song into a powerful rock anthem. The lyric “How does it feel, to treat me like you do?” evolves from a lament into an angry roar, adding a new layer of intensity to the familiar lyrics. Orgy’s “Blue Monday” stands as a compelling reinterpretation that brought the song to a new audience.
81. *NSYNC, “I Drive Myself Crazy” (No. 67, Hot 100)
*NSYNC posing for a portrait in 1999*NSYNC pose for a portrait in August 1999 portrait in Los Angeles. Bob Berg/Getty Images
*NSYNC’s “I Drive Myself Crazy,” the final single from their self-titled debut album, showcased a softer side of the boy band. This quasi-power ballad highlighted Chris Kirkpatrick on lead vocals, a departure from the usual Justin Timberlake and JC Chasez spotlights. While not a chart-topper, the music video became a TRL staple, capturing the essence of late 90s pop culture with a cameo from Elisa Donovan of Clueless. Although the music video’s mental health themes might be viewed differently today, the song itself remains a well-crafted and enduring ballad.
80. Armand Van Helden feat. Duane Harden, “You Don’t Know Me” (No. 2, Dance Club Songs)
Armand Van Helden’s “You Don’t Know Me” is a Frankensteinian dance track, expertly blending samples from various eras of dance music. It combines 70s disco strings, early 90s house drums, and the powerful vocals of Duane Harden into a potent club anthem. This unique combination propelled “You Don’t Know Me” to No. 2 on the Dance Club Songs chart and even topped the UK charts, demonstrating its widespread appeal and innovative sound.
79. B.G. feat. Baby, Turk, Mannie Fresh, Juvenile & Lil Wayne, “Bling Bling” (No. 36, Hot 100)
B.G.’s “Bling Bling,” featuring the Cash Money Records crew, introduced a new catchphrase into the cultural lexicon. Before Lil Wayne’s superstardom, “Bling Bling” and its infectious Mannie Fresh beat became a top 40 hit. The song’s video, fronted by B.G., popularized the term “bling bling,” which even made its way into Merriam-Webster’s dictionary. While the phrase’s cultural prominence has faded, the song’s energetic beat and celebratory vibe remain undeniable.
78. Ginuwine, “So Anxious” (No. 16, Hot 100)
Ginuwine’s “So Anxious” is a smooth and confident R&B classic from the turn of the millennium. With songwriting by Static Major and production by Timbaland, the track had a recipe for success from the start. Ginuwine’s signature falsetto, particularly the drawn-out “soooooo anxious” in the chorus, elevates the song to another level. While not as groundbreaking as “Pony,” “So Anxious” delivers everything fans loved about grown-and-sexy late-90s R&B.
77. Donell Jones feat. Lisa “Left Eye” Lopes, “U Know What’s Up” (No. 7, Hot 100)
Donell Jones’s “U Know What’s Up,” featuring Lisa “Left Eye” Lopes, is a smooth and suggestive R&B track that celebrates summer romance. This song, part of the “horny ode to the sundress” microgenre, evokes images of warm weather, stylish cars, and carefree flirtation. Eddie F. and Darren Light’s production creates a sticky, infectious groove that perfectly complements the suggestive lyrics. Even without fully focusing on the lyrics, the song’s vibe is undeniably sensual and captivating.
76. System of a Down, “Sugar” (No. 28, Mainstream Rock)
System of a Down posing for a portrait in 1999System of a Down pose for a portrait in July 1999 in Los Angeles. Bob Berg/Getty Images
System of a Down’s “Sugar” was the perfect debut single to introduce the Armenian-American alt-metal band to the world. Capturing the raw energy of their live performances, “Sugar” showcases the band’s signature sound: pummeling riffs, dynamic shifts between singing and screaming, and unpredictable tempo changes. At the dawn of nu-metal’s mainstream dominance, “Sugar” demonstrated the genre’s potential for innovation and intensity.
75. D’Angelo feat. Method Man and Redman, “Left and Right” (No. 70, Hot 100)
D’Angelo’s collaboration with Method Man and Redman on “Left and Right” might seem unexpected on paper, but the result is a seamless blend of soul and hip-hop swagger. This track from the Voodoo album showcases the effortless virtuosity of all three artists. “Left and Right” eases into its groove, with D’Angelo’s smooth vocals and Method Man and Redman’s laid-back flows creating a captivating chemistry. The song’s relaxed vibe and understated cool make it a standout collaboration.
74. Monica, “Angel of Mine” (No. 1, Hot 100)
Monica’s “Angel of Mine,” a cover of a UK hit by Eternal, became a massive success stateside, earning Monica her third Hot 100 No. 1 hit. This endearing love song resonated with audiences, showcasing Monica’s winning vocal delivery and emotional depth. The mid-tempo ballad’s simple yet heartfelt lyrics, like “I look at you, looking at me/ Now I know why they say the best things are free,” express profound emotion with economy, reminiscent of Smokey Robinson’s songwriting.
73. Mobb Deep feat. Lil Kim, “Quiet Storm” (Remix) (No. 17, Rap Songs)
Mobb Deep’s “Quiet Storm” remix, featuring Lil Kim, reimagines the “quiet storm” concept within a hip-hop context. While “quiet storm” typically evokes images of rainy nights and romantic R&B ballads, Mobb Deep transformed it into a chilling club anthem. Utilizing a subsonic bass sample from Grandmaster Flash and Lil Kim’s iconic verse, the Queensbridge legends created a unique track that blends club energy with introspective undertones, setting a precedent for future rappers.
72. 702, “Where My Girls At” (No. 4, Hot 100)
702’s “Where My Girls At,” penned by Missy Elliott, became a defining ladies’ anthem of the late 90s. Alongside classics from Destiny’s Child and TLC, “Where My Girls At” celebrated female camaraderie and empowerment. Although the verses might not be as commanding as other girl group anthems, the song boasts an incredibly infectious chorus that instantly grabs listeners. No matter the setting, once the chorus of “Where My Girls At” kicks in, it’s impossible not to sing along.
71. Rage Against the Machine, “Guerrilla Radio” (No. 69, Hot 100)
Rage Against the Machine’s “Guerrilla Radio” is a scorching call to arms that resonated with both mainstream audiences and social justice advocates. For nearly a decade, the band had been outspoken proponents of social change, and “Guerrilla Radio” became their most potent and widely heard manifesto. Its adrenaline-pumping energy made it popular among gamers and earned it a Grammy Award, demonstrating its widespread impact and enduring appeal.
70. H.O.T., “I Yah!” (Did not chart)
H.O.T.’s “I Yah!” a hit from the first generation K-pop idol group, stands out for its intense and genre-bending sound. This rage-fueled anthem blends smooth orchestral elements with heavy metal and hard rock influences, including wailing guitars and aggressive vocals. Released with a visually striking music video inspired by Japan’s visual kei scene, “I Yah!” tackled social corruption and youth frustration, inspired by a tragic fire caused by bribery and unsafe conditions at a youth camp.
69. Moby, “Bodyrock” (No. 6, Dance Club Songs)
Moby’s “Bodyrock,” from his breakout album Play, captures his genius as a dance music artist. While Play features more ambitious tracks, “Bodyrock” with its jagged guitar riffs and Spoonie Gee samples, is pure dance floor energy. Despite initial comparisons to Fatboy Slim, “Bodyrock” achieves a unique euphoric release. The song’s spazztastic music video perfectly complements its frenetic energy, making “Bodyrock” an anthem for letting loose and embracing individuality.
68. Black Star feat. Common, “Respiration” (No. 54, R&B/Hip-Hop Songs)
Black Star’s “Respiration,” featuring Common, is a tribute to the grit and complexity of city life. Featured on their debut album Mos Def and Talib Kweli Are Black Star, “Respiration” crept onto the charts months after the album’s release, highlighting the song’s slow-burning impact. The track paints a vivid picture of urban life, exploring both its challenges and its transformative power. “Respiration” remains Black Star’s last single to date, leaving fans hoping for more music from the duo.
67. TLC, “Unpretty” (No. 1, Hot 100)
TLC posing for a studio portrait in 1999TLC pose for a studio portrait circa 1999 in Hollywood, Calif Ron Davis/Getty Images
TLC continued their reign as one of the most empowering girl groups of the 90s with “Unpretty.” This alt-rock influenced track from FanMail tackled the issue of insecurities and self-worth, delivering a powerful message of self-love and acceptance. Twenty years later, “Unpretty” remains relevant, emphasizing that true beauty comes from within and challenging unrealistic physical standards.
66. Wilco, “A Shot in the Arm” (Did not chart)
Wilco’s “A Shot in the Arm” is a raw and unflinching portrayal of addiction from songwriter Jeff Tweedy. The song’s repetitive structure mirrors the cyclical nature of habit, and Tweedy’s evocative lyrics, like “The ashtray says you’ve been up all night,” paint a vivid picture of late-night struggles. The song builds to a powerful climax as Tweedy’s vocals become increasingly strained, culminating in a harrowing comedown that underscores the song’s complex emotional landscape.
65. Garbage, “Special” (No. 52, Hot 100)
Garbage’s “Special” is a sultry and assertive track fronted by Shirley Manson’s commanding vocals. The song dismantles a failed relationship with sharp directness, delivered over Butch Vig’s signature electronic-influenced production. Manson’s lyrics, like “There’s no way in hell I’d take you back,” are both cutting and captivating. The song’s borrowed lament from Chrissie Hynde’s “Talk of the Town” adds a layer of knowing musicality, solidifying Garbage’s place in the minds of listeners.
64. Phil Collins, “You’ll Be in My Heart” (No. 21, Hot 100)
Phil Collins, a chart-topping force in the 20th century, delivered another hit with “You’ll Be in My Heart” from the Tarzan soundtrack. Collins wrote and composed the entire soundtrack, and “You’ll Be in My Heart” stands out as one of his most memorable performances. Transforming what could have been a cheesy Disney track into a genuinely heartfelt lullaby, Collins cemented its status as an all-time great Disney song, earning him an Oscar and a Golden Globe.
63. Kelis, “Caught Out There” (No. 54, Hot 100)
Kelis burst onto the scene in 1999 with the unforgettable “Caught Out There,” a visceral and dramatic debut single. While not achieving immediate mainstream omnipresence, Kelis made a powerful impact with this track, fueled by its raw emotion and The Neptunes’ innovative production. The song’s bilious chorus, punctuated by Kelis’ scream, and the chaotic, siren-like beat created a sound unlike anything else on the radio, hinting at a long and influential career to come.
62. Jamiroquai, “Canned Heat” (No. 1, Dance Club Songs)
Jamiroquai’s “Canned Heat” is a vibrant and funky track that resonated during a period of global political turmoil. With its jazzy intro and infectious bassline, “Canned Heat” is pure groove. Jay Kay’s decision to prioritize the boogie resulted in the group’s second Dance Club Songs No. 1 hit, proving that the song’s timeless disco-funk sound transcended eras.
61. Fastball, “Out of My Head” (No. 20, Hot 100)
Fastball’s “Out of My Head” is a unique 90s pop song with an iconic organ intro. Unusually structured, the song primarily consists of its chorus repeated multiple times with minimal verses. Yet, this unconventional structure works, creating an earworm that listeners might hear countless times before noticing its unusual form. Its catchy melody and distinctive organ riff have ensured its lasting appeal, even inspiring a 2017 interpolation by Machine Gun Kelly and Camila Cabello.
60. Vengaboys, “Boom Boom Boom Boom” (No. 84, Hot 100)
Vengaboys’ “Boom Boom Boom Boom!!” is a quintessential Eurodance anthem that evokes a complex mix of emotions. While seemingly simple and euphoric, the song’s synth melodies and chord progression create a bittersweet, almost melancholic undertone beneath the surface of its happy-go-lucky exterior. The childlike lyrics about lasting love are juxtaposed with a sense of pent-up energy, making “Boom Boom Boom Boom!!” a surprisingly nuanced and memorable dance track.
59. Lauryn Hill, “Everything Is Everything” (No. 35, Hot 100)
Lauryn Hill’s “Everything Is Everything” showcases her multifaceted talent as both a rapper and singer. This track from The Miseducation of Lauryn Hill seamlessly blends social commentary with soulful melodies. Hill’s verses address injustice and urban struggles, while her soothing chorus offers hope and resilience. Her effortless flow and lyrical dexterity, proclaiming herself “more powerful than two Cleopatras,” solidify her status as a singular force in music.
58. Sugar Ray, “Every Morning” (No. 3, Hot 100)
Sugar Ray performing on The Tonight Show with Jay Leno in 1999Sugar Ray perform on The Tonight Show with Jay Leno on April 6, 1999. NBC/NBCU Photo Bank via Getty Images
Sugar Ray’s “Every Morning” is a masterclass in hiding raunchy lyrics behind incredibly catchy hooks. The song’s upbeat and infectious riff makes the opening line, “Every morning there’s a halo hanging from the corner of my girlfriend’s four-post bed,” deceptively fun to sing along to. Whether listeners were aware of the song’s possibly suggestive lyrical content, “Every Morning” became a massive hit thanks to its playful melody and undeniable earworm quality, cementing Sugar Ray’s status as pop music tricksters.
57. Brad Paisley, “He Didn’t Have to Be” (No. 30, Hot 100)
Brad Paisley’s “He Didn’t Have to Be” is a heartfelt and moving story song about the bond between a stepson and stepfather. While not autobiographical for Paisley, his earnest delivery makes the story feel deeply personal. Co-written with Kelley Lovelace, the song’s theme of a growing, positive stepfamily relationship resonated deeply with listeners, becoming Paisley’s first of many country radio No. 1 hits and remaining a popular song to this day.
56. Creed, “Higher” (No. 7, Hot 100)
Creed’s “Higher” is an anthemic rock track that propelled the band to mainstream success. Scott Stapp’s powerful vocals and Mark Tremonti’s distinctive guitar riff define the song’s soaring energy. The chorus, “Can you take me higher?” became a rallying cry for fans, and the song’s success contributed to their album Human Clay achieving Diamond certification. While Creed might not have been considered “cool” by some, “Higher” and their string of hits demonstrated the undeniable power of their anthemic rock sound.
55. Lil Wayne, “Tha Block Is Hot” (No. 65, Hot 100)
Lil Wayne’s “Tha Block Is Hot” introduced a young and confident artist poised for superstardom. At just 16 years old, Lil Wayne’s solo debut showcased his charisma and unique personality. The track’s skittering Mannie Fresh beat provided the perfect backdrop for Wayne’s nimble flow and playful delivery. Even at this early stage in his career, “Tha Block Is Hot” revealed the irresistible charm and talent that would make Lil Wayne a defining artist of the 21st century.
54. Faith Hill, “Breathe” (No. 2, Hot 100)
Faith Hill’s “Breathe” solidified her crossover appeal with its sultry and timeless balladry. Released in late 1999, “Breathe” showcased Hill’s delicate yet powerful vocals, seamlessly transitioning from whispers to belts. The song’s minimal production and enduring quality made it a hit on both pop and country radio, spending weeks at No. 1 on the Hot Country Songs chart and reaching No. 2 on the Hot 100, becoming a karaoke and radio staple.
53. Q-Tip, “Vivrant Thing” (No. 26, Hot 100)
Q-Tip’s “Vivrant Thing” is a funky and romantic hip-hop track that stands as a follow-up to his earlier classic, “Bonita Applebum.” This solo hit shimmies and grooves with a unique energy, driven by a tight rhythm section of slapping guitar and hissing hi-hats. Beyond the song’s infectious funk, “Vivrant Thing” is set apart by its genuine reverence for the subject of Q-Tip’s affection, celebrating her intelligence and engaging personality alongside her physical allure.
52. Basement Jaxx, “Red Alert” (No. 1, Dance Club Songs)
Basement Jaxx’s “Red Alert” is a dance floor classic built around a monstrous hook. The song’s impossibly funky bassline is teased in a muffled intro before exploding into full force. Fluttering electro echoes, screaming synths, and a powerhouse vocal propel this soulful house track to No. 1 on the Dance Club Songs chart. “Red Alert” is a masterclass in building tension and release on the dance floor.
51. Shania Twain, “That Don’t Impress Me Much” (No. 7, Hot 100)
Shania Twain photographed in 1999Shania Twain photographed in 1999. Mick Hutson/Redferns
Shania Twain’s “That Don’t Impress Me Much” became an enduring anthem of female self-assurance and independence. Years after its release, the song’s pop culture references, like Brad Pitt, still resonate, proving its lasting legacy. “That Don’t Impress Me Much” was one of Twain’s many top 40 hits, pioneering a sound that would later influence Taylor Swift’s pop-country revolution, demonstrating Twain’s lasting impact on popular music.
50. Blink-182, “What’s My Age Again?” (No. 58, Hot 100)
Blink-182’s “What’s My Age Again?” is synonymous with youthful immaturity and carefree rebellion. The iconic music video, featuring the band running naked through the streets, perfectly captured the song’s spirit. “What’s My Age Again?” became a mission statement for the pop-punk trio, celebrating the joys of pranks and cartoons over adult responsibilities, resonating with a generation embracing youthful exuberance.
49. Fiona Apple, “Fast As You Can” (No. 20, Alternative Songs)
Fiona Apple’s “Fast As You Can” is a mature and complex track that showcases her singular talent. Standing apart from the manufactured pop of the 90s, Apple carved out a unique space with her introspective and musically adventurous sound. “Fast As You Can” hints at relationship complexities with lyrics like “I’ll soar the uneven wind, complain and blame the sterile land,” while her moody vocals and the song’s driving percussion create a spellbinding atmosphere.
48. Aphex Twin, “Windowlicker” (Did not chart)
Aphex Twin’s “Windowlicker” is a surreal and groundbreaking track with a music video that predates modern internet humor. The video’s juxtaposition of bikini-clad women slow-motion dancing to such an unconventional dance track was both shocking and thought-provoking. “Windowlicker” itself is a sonic black hole, blending noise, ambient, breakbeats, and turntable techniques into a barely comprehensible yet strangely captivating form of pop music, defying categorization and expectations.
47. Backstreet Boys, “Larger Than Life” (No. 25, Hot 100)
Backstreet Boys’ “Larger Than Life” lived up to its title in every way, becoming a monumental hit in 1999. From its expensive music video to its bombastic live performances, “Larger Than Life” felt like an event. AJ McLean’s scream, the guitar solo, and the massive hook all contributed to the song’s titanic scale. “Larger Than Life” became Millennium‘s anthem, ringing in a new era for the boy band and for pop music itself, setting a high bar for BSB choruses to follow.
46. OutKast, “Da Art of Storytellin’ (Pt. 1)” (No. 67, R&B/Hip-Hop Songs)
OutKast’s “Da Art of Storytellin’ (Pt. 1)” showcases Big Boi and André 3000’s lyrical mastery and storytelling prowess. Positioning hip-hop as a platform for narrative, the duo trade tales with precision and dexterity over a hustling beat. The song’s multi-generational impact is evident in samples and homages from artists like Kanye West and J. Cole, proving its enduring influence on hip-hop storytelling.
45. Hole, “Malibu” (No. 81, Hot 100)
Hole’s “Malibu” offered a softer and more vulnerable side to Courtney Love’s songwriting. In contrast to the snarling energy of “Celebrity Skin,” “Malibu” revealed a cathartic and grieving softness. Co-written with Eric Erlandson and Billy Corgan, “Malibu” peeled back Love’s tough exterior to reveal emotional depth, earning the band a Grammy nomination and showcasing their range beyond hard-rocking anthems.
44. Brian McKnight, “Back at One” (No. 2, Hot 100)
Brian McKnight’s “Back at One” is a smooth and heartfelt R&B ballad that highlights his signature vocals and falsetto. Written solely by McKnight, the song’s promise of unwavering love resonated deeply with listeners, becoming one of his biggest hits and a popular wedding song. Covered by numerous artists across genres and languages, “Back at One” remains a timeless and swoon-worthy love song.
43. LFO, “Summer Girls” (No. 3, Hot 100)
LFO’s “Summer Girls” is an unconventional and quirky love song that became a late-90s pop culture phenomenon. Referencing Paul Revere, New Kids on the Block, and Abercrombie & Fitch, the song’s lyrics are intentionally random and nonsensical. Yet, “Summer Girls” manages to convey the feeling of a fleeting summer romance with its catchy guitar riff and frontman Rich Cronin’s rap-like delivery of pop culture references, becoming a timelessly lovable and slightly bizarre pop hit.
42. Mos Def, “Ms. Fat Booty” (No. 54, R&B/HIp-Hop Songs)
Mos Def’s “Ms. Fat Booty” is a smooth and soulful track built around a hypnotic sample of Aretha Franklin’s “One Step Ahead.” This debut solo single showcased Mos Def’s effortless flow and storytelling ability. While the song’s subject matter might be interpreted as a “thirst trap” in modern terms, “Ms. Fat Booty” ultimately reveals a hopeless romantic narrator captivated by a free-spirited woman, adding depth and complexity to the track.
41. Lit, “My Own Worst Enemy” (No. 51, Hot 100)
Lit’s “My Own Worst Enemy” is a quintessential pop-punk anthem that defined the sound of 1999. From its opening guitar roar, the song’s energy is undeniable. Its repetitive guitar riffs, sing-song melodies, and relatable lyrics about youthful mistakes resonated with a generation. “My Own Worst Enemy” paved the way for bands like Sum 41 and New Found Glory, and its universal message about making (drunk) mistakes ensures its enduring appeal.
40. Lou Bega, “Mambo No. 5” (No. 3, Hot 100)
Lou Bega’s “Mambo No. 5” became a global phenomenon in 1999, perfectly timed for the booming economy and summer vibes. This German artist’s reworking of a Cuban song became a smash hit across continents, appealing to diverse audiences. Even a Radio Disney edit with Disney characters replaced Bega’s female interests, highlighting its widespread appeal. “Mambo No. 5” with its infectious horns and danceable rhythm, had something for everyone, becoming a ubiquitous and unforgettable summer anthem.
39. Britney Spears, “(You Drive Me) Crazy” (The Stop Remix) (No. 10, Hot 100)
Britney Spears’ “(You Drive Me) Crazy” (The Stop Remix) amplified the energy of her debut album, turning yearning into obsession. While the original version was already a hit, the remix for the Drive Me Crazy soundtrack took the song to another level. The reworked version retained the catchy cowbell and added re-recorded vocals, a spine-tingling intro, and the iconic “Stop!” interjection, transforming “(You Drive Me) Crazy” into a truly mind-blowing pop anthem.
38. Dixie Chicks, “Cowboy Take Me Away” (No. 27, Hot 100)
Dixie Chicks’ “Cowboy Take Me Away” showcased their signature harmonies and country roots amidst the pop-country crossover wave. While Shania Twain and Faith Hill embraced pop influences, Dixie Chicks held down the traditional country sound with their powerful vocals and yearning fiddle. “Cowboy Take Me Away” expresses a romantic longing for simpler times and the hope that love can offer salvation, reminding listeners of the power of their voices and their country authenticity.
37. Lee Jung Hyun, “Wa” (Did not chart)
Lee Jung Hyun’s “Wa” marked the arrival of a transformative K-pop artist. Known as the Queen of Transformation, Lee Jung Hyun’s performances are theatrical and visually stunning. “Wa,” her debut single, blends traditional Korean instruments with pulsating techno beats, confronting Korea with a futuristic sound that would define her career. Her bold vision paid off, with “Wa” now considered a classic of first-generation K-pop, even attracting the attention of Lady Gaga.
36. KoRn, “Freak on a Leash” (No. 6, Alternative Songs)
KoRn’s “Freak on a Leash” is forever linked to its groundbreaking and cinematic music video, which dominated MTV’s Total Request Live. However, the song itself is a pure distillation of KoRn’s nu-metal appeal. Full choruses, twitchy guitar effects, Jonathan Davis’s creepy vocals, and nonsensical bridges all combine to create a rush of energy and raw emotion. “Freak on a Leash” remains a defining track of the nu-metal era, showcasing the genre’s enduring power.
35. Mandy Moore, “Candy” (No. 41, Hot 100)
Mandy Moore attending the 1999 Billboard Music AwardsMandy Moore attends the 1999 Billboard Music Awards at MGM Grand Hotel on Dec. 8, 1999 in Las Vegas. Scott Harrison/Hulton Archive/Getty Images
Mandy Moore’s “Candy” presented a sweeter and more wholesome alternative to the edgier teen pop of Britney Spears and Christina Aguilera. Moore’s debut single, released when she was just 15, offered a sugary-pop sound and squeaky-clean image that appealed to a younger audience. While peaking at No. 41, “Candy” with its shimmering intro, catchy “missing you like candy” lyric, and spoken-word bridge, became an addictive and unmissable pop hit, establishing Mandy Moore in the teen pop landscape.
34. Enrique Iglesias, “Bailamos” (No. 1, Hot 100)
Enrique Iglesias’ “Bailamos” marked his crossover to English-language markets and solidified the Latin pop explosion of 1999. This flamenco-infused mid-tempo anthem became irresistible to audiences worldwide, reaching No. 1 on the Hot 100. Featured on both the Wild Wild West soundtrack and Iglesias’ debut English album Enrique, “Bailamos” launched a crossover career that would make Iglesias a consistent presence on both pop and Latin radio for years to come.
33. Tal Bachman, “She’s So High” (No. 14, Hot 100)
Tal Bachman’s “She’s So High” is a buoyant and pure pop-rock ode to an unattainable love interest. This song, with its references to Cleopatra, Joan of Arc, and Aphrodite, and its euphoric chorus, is almost saccharine in its wholesomeness. The oh-so-90s music video and Bachman’s earnest delivery further contribute to the song’s charm. “She’s So High” may have been a one-hit-wonder for Tal Bachman, but its earnest depiction of hopeless love remains a beloved 90s classic.
32. The Roots feat. Erykah Badu, “You Got Me” (No. 39, Hot 100)
The Roots’ “You Got Me,” featuring Erykah Badu, is their sole top 40 hit, showcasing their ability to blend hip-hop with soulful storytelling. This dual-perspective relationship song resonated with both their core fanbase and mainstream audiences. “You Got Me” is a love song about commitment and support through challenging times. The minor-key melody and drum-and-bass outro add layers of complexity, while the chorus offers a comforting assurance: “Baby, don’t worry, you know that you got me.”
31. Madonna, “Beautiful Stranger” (No. 19, Hot 100)
Madonna’s “Beautiful Stranger,” a soundtrack single, embraced psychedelic influences, surprising some fans and intriguing new listeners. The song’s 60s-inspired sound, reminiscent of Love’s “She Comes in Colors,” blended seamlessly with a modern pop sensibility, fitting in alongside Britney and Christina on top 40 radio. Co-written with William Orbit, “Beautiful Stranger” won a Grammy for best song written for visual media, Madonna’s only Grammy for songwriting to date.
30. Eiffel 65, “Blue (Da Ba Dee)” (No. 6, Hot 100)
Eiffel 65’s “Blue (Da Ba Dee)” is an absurd and unforgettable Eurodance anthem. Dismissed by some as ridiculous “Eurocheese,” “Blue” embraces its high-camp aesthetic with Auto-Tune vocals and nonsensical lyrics. This Italian group’s French-named song about a color became a global phenomenon precisely because of its absurdity, becoming the definitive absurd European dance-pop song.
29. Björk, “All Is Full of Love” (Did not chart)
Björk’s “All Is Full of Love” is a visually and sonically stunning track with a groundbreaking music video. Directed by Chris Cunningham, the video features android Björks in a sweet and unsettling love scene, pushing the boundaries of late-90s computer animation. Sonically, the song blends a trip-hop beat with ethereal harps and violins, conveying a message of universal love and affection with a futuristic and otherworldly beauty.
28. Ol’ Dirty Bastard feat. Kelis, “Got Your Money” (No. 33, Hot 100)
Ol’ Dirty Bastard’s “Got Your Money,” featuring Kelis, showcases his unique and eccentric artistry. ODB, one of music’s most idiosyncratic figures, delivered a track that is both crude and undeniably catchy. From the too-literal opening verse to his unpredictable flow, ODB’s personality shines through. Kelis’ earworm hook and ODB’s surreal world of excess and insanity combine to create a crossover hit that is unlike anything else.
27. Sixpence None the Richer, “Kiss Me” (No. 2, Hot 100)
Sixpence None the Richer performing on The Tonight Show with Jay Leno in 1999Sixpence None the Richer on The Tonight Show with Jay Leno on March 19, 1999. Margaret Norton/NBC/NBCU Photo Bank via Getty Images
Sixpence None the Richer’s “Kiss Me” is a mushy, cute, and vulnerable pop song that perfectly captures the feeling of falling in love. Featured in Dawson’s Creek and numerous teen movies, “Kiss Me” became a soundtrack to young romance and countless proposals. This Nashville folk-pop group’s breakthrough hit spent 16 weeks in the Hot 100’s top 10, becoming a lasting anthem of love and affection.
26. Mariah Carey feat. Jay-Z, “Heartbreaker” (No. 1, Hot 100)
Mariah Carey’s “Heartbreaker,” featuring Jay-Z, perfected her signature blend of pop and hip-hop. Carey, a pioneer in featuring rappers on pop tracks, teamed up with Jay-Z for this lead single from Rainbow. Built around a sample of Stacy Lattisaw’s “Attack of the Name Game,” “Heartbreaker” combined Carey’s swooning vocals with Jay-Z’s playful rhymes. The music video, one of the most expensive ever made, further cemented the song’s iconic status, solidifying Carey’s reign as a pop diva.
25. Celine Dion, “That’s the Way It Is” (No. 6, Hot 100)
Celine Dion’s “That’s the Way It Is” marked her final top 10 hit of the 20th century, shifting away from the high drama of “My Heart Will Go On” towards a softer, adult-contemporary sound. Released as a new single on her greatest hits compilation, “That’s the Way It Is” embraced a more pillowy and self-affirming message, reminiscent of country-pop artists like Faith Hill and Shania Twain. Dion’s stellar vocals and the song’s corniness combined for a blissful and memorable pop hit.
24. Red Hot Chili Peppers, “Scar Tissue” (No. 9, Hot 100)
Red Hot Chili Peppers’ “Scar Tissue” marked a triumphant comeback for the band after a period of challenges. This wistful and confessional track mixed lyrics about loneliness with subtle motivation and a killer guitar solo from returning guitarist John Frusciante. Anthony Kiedis described it as a “phoenix-rising-from-the-ashes vibe,” and “Scar Tissue” indeed won a Grammy and served as the lead single for Californication, re-establishing RHCP as superstars.
23. Jay-Z feat. Amil, “N—a What, N—a Who (Originator 99)” (No. 84, Hot 100)
Jay-Z’s “N—a What, N—a Who (Originator 99),” featuring Amil, marked the beginning of his long-standing musical partnership with Timbaland. Featured on Vol. 2… Hard Knock Life, Timbaland’s production on this track is futuristic and frenetic. Jay-Z returned to a rapid-fire, double-time flow, matching the song’s urgent energy. “N—a What, N—a Who” showcased the dynamic chemistry between Jay-Z and Timbaland, launching a two-decade-long collaboration.
22. Whitney Houston, “It’s Not Right, But It’s OK” (No. 4, Hot 100)
Whitney Houston performing at the 1999 Brit AwardsWhitney Houston performs at the 1999 Brit Awards on Feb. 16, 1999 in London. Fiona Hanson/PA Images via Getty Images
Whitney Houston’s “It’s Not Right, But It’s OK” showcased a new assertive and empowered persona. After years of being criticized as an “Ice Queen,” Houston shed that image with this track, scolding a cheating partner with confidence and attitude. Backed by a slick Darkchild beat, “It’s Not Right, But It’s OK” presented a revamped Whitney, both vocally and visually, leaving fans wondering what her career trajectory might have been had this personality been showcased earlier.
21. Smash Mouth, “All Star” (No. 4, Hot 100)
Smash Mouth’s “All Star” became a cultural phenomenon in 1999, and its meme-ability has ensured its continued relevance. Immediately catchy and fun to sing along to, “All Star” peaked at No. 4 on the Hot 100 and spent 30 weeks on the chart. Featured in Shrek in 2001, “All Star” experienced a resurgence in popularity in 2017 due to internet memes and remixes, proving its enduring appeal and solidifying its place in pop culture.
20. DMX, “Ruff Ryders Anthem” (No. 94, Hot 100)
DMX’s “Ruff Ryders Anthem” is a raw and energetic hip-hop banger that became a defining track of his career. The song’s booming energy and DMX’s aggressive persona made it a crowd-pleaser at concerts and sporting events. “Ruff Ryders Anthem” captured the raw energy of late-90s hip-hop, becoming an anthem for mobbing with your crew and elevating team morale.
19. Len, “Steal My Sunshine” (No. 9, Hot 100)
Len’s “Steal My Sunshine” became the unofficial song of the summer of 1999 with its breezy and infectious vibe. Amidst Y2K anxieties and millennial fear-mongering, “Steal My Sunshine” offered a carefree escape, driven by a giddy sample from Andrea True Connection’s “More, More, More.” The song’s playful piano riff, woodblock percussion, and interplay between Marc and Sharon Costanzo’s vocals created a sound that perfectly captured the feeling of a day at the beach, becoming a one-hit-wonder that remains a nostalgic summer classic.
18. Fatboy Slim, “Praise You” (No. 36, Hot 100)
Fatboy Slim’s “Praise You” is a sample-heavy pop classic accompanied by an iconic and award-winning music video. The Torrance Community Dance Group’s amateur performance outside a Los Angeles multiplex, directed by Spike Jonze, perfectly captured the song’s joyful and communal spirit. Built around a soul sample and piano melody, “Praise You” is a jubilant and uplifting dance track that became a late-90s dance-pop anthem.
17. Missy Elliott feat. Nas, Eve & Q-Tip “Hot Boyz” (No. 5, Hot 100)
Missy Elliott’s “Hot Boyz” remix, featuring Nas, Eve, and Q-Tip, is a star-studded posse cut that showcases Missy’s collaborative genius. This track, from her sophomore album Da Real World, set a Hot Rap Singles record, topping the chart for 18 weeks. Each featured artist brings their A-game, with Nas, Eve, and Q-Tip delivering memorable verses alongside Missy’s sultry hook and Timbaland’s futuristic production, creating a truly “hot” hip-hop track.
16. Foo Fighters, “Learn to Fly” (No. 19, Hot 100)
Foo Fighters’ “Learn to Fly” is a soaring and triumphant rock anthem with an equally iconic music video. Beyond the goofy visuals, “Learn to Fly” is a well-crafted song with an unforgettable opening riff and a sunny, catchy chorus. Following up action-packed hits like “Everlong” and “My Hero” was no easy task, but “Learn to Fly” proved to be a triumph in its own right, becoming a Foo Fighters classic and a rock radio staple.
15. Destiny’s Child, “Bills, Bills, Bills” (No. 1, Hot 100)
Destiny’s Child’s “Bills, Bills, Bills” became a defining anthem of female independence and financial responsibility. Written by Kevin “She’kspere” Briggs and Kandi Burruss, this sassy R&B track called out deadbeat men with playful lyrics and a harpsichord-synth-led beat. Beyoncé, pre-solo superstardom, shines in the lead role, scolding freeloaders and turning “cell phone” into a six-syllable phrase. “Bills, Bills, Bills” became a No. 1 hit and a timeless anthem for women everywhere.
14. Dr. Dre feat. Snoop Dogg, “Still D.R.E.” (No. 93, Hot 100)
Dr. Dre’s “Still D.R.E.,” featuring Snoop Dogg, marked a triumphant return for the West Coast hip-hop legend. With its iconic staccato piano hook, “Still D.R.E.” ushered in Dre’s 2001 era. Co-written by Jay-Z, the track is a braggadocious career retrospective, celebrating Dre’s achievements and enduring influence on hip-hop. Featuring Snoop Dogg, “Still D.R.E.” became an instant classic, solidifying Dr. Dre’s legacy as a hip-hop icon.
13. Ricky Martin, “Livin’ La Vida Loca” (No. 1, Hot 100)
Ricky Martin’s “Livin’ La Vida Loca” became a global sensation, sparking a Latin pop explosion and turning Martin into a platinum superstar. Despite some questionable lyrics, “Livin’ La Vida Loca” is a near-perfect pop song, driven by canned horns, surf-rock guitar, and Martin’s irresistible charm. The song’s energy and infectious rhythm made it inescapable on pop radio in 1999, solidifying its place as a defining track of the year and of Latin pop’s crossover moment.
12. Shania Twain, “Man! I Feel Like a Woman” (No. 23, Hot 100)
Shania Twain’s “Man! I Feel Like a Woman” is an explosive anthem of female empowerment and fun. The song’s iconic synth riff and Twain’s commanding vocals create an electrifying energy. Celebrating female freedom and the right to have a good time, “Man! I Feel Like a Woman” became a mission accomplished, a four-minute romp of raised voices, short skirts, and hair-down liberation, solidifying Twain’s status as a female icon.
11. Christina Aguilera, “Genie in a Bottle” (No. 1, Hot 100)
Christina Aguilera’s “Genie in a Bottle” launched her career and set her apart from her teen pop contemporaries. With its soulful sound, squelching beat, and self-respecting lyrics, “Genie in a Bottle” presented a more mature and vocally impressive teen pop star. Aguilera’s powerful vocals, even at a young age, and the song’s message about respecting boundaries resonated with audiences, making “Genie in a Bottle” a defining debut single and a lasting pop classic.
10. Eminem, “My Name Is” (No. 36, Hot 100)
Eminem’s “My Name Is” introduced a controversial and groundbreaking new voice in hip-hop. This debut single from The Slim Shady LP showcased Eminem’s witty, sarcastic, and often offensive sense of humor. Sampling Labi Siffre’s “I Got The,” Dr. Dre’s production created a cartoonish backdrop for Eminem’s irreverent lyrics, targeting pop culture and celebrities with gleeful abandon. “My Name Is” became a top 40 hit and earned Eminem his first Grammy, signaling the arrival of a major and unapologetically provocative force in music.
9. Jennifer Lopez, “Waiting For Tonight” (No. 8, Hot 100)
Jennifer Lopez’s “Waiting For Tonight” from her debut album On the 6 stands out as one of her most enduring hits. With universal themes, infectious music, and a timeless chorus, “Waiting For Tonight” oozes sex appeal and anticipation. Lopez’s sultry vocals, the song’s guitar strums, and pulsating beat create a passionate and romantic atmosphere. “Waiting For Tonight” remains a timeless and universally appealing pop anthem.
8. Blink-182, “All the Small Things” (No. 6, Hot 100)
Blink-182’s “All the Small Things” is a glistening pop-punk moment that playfully poked fun at boy bands while becoming a pop classic itself. Written about Tom DeLonge’s girlfriend, “All the Small Things” embraced its pop sensibilities, casting Blink-182 as a self-aware, skate park boy band. Producer Jerry Finn’s pop-punk production and the song’s infectious “na-na, na-na” chorus made “All the Small Things” a defining pop-punk anthem and a lasting hit.
7. Cher, “Believe” (No. 1, Hot 100)
Cher performing live in 1999Cher sings the national anthem at Super Bowl XXXIII which was held at Pro Player Stadium on Jan. 31, 1999 in Miami. Al Pereira/Michael Ochs Archives/Getty Images
Cher’s “Believe” is most famous for its groundbreaking use of Auto-Tune, but its impact goes far beyond vocal effects. The song’s hook, Cher’s powerful vocals, and empowering message of resilience made it a global phenomenon. While not officially credited as a songwriter, Cher contributed to the lyrics, turning a potentially whiny song into an anthem of strength and reinvention. “Believe” became one of the best-selling singles of all time, resonating across dance floors decades later and marking a major comeback for Cher.
6. Lauryn Hill, “Ex-Factor” (No. 21, Hot 100)
Lauryn Hill’s “Ex-Factor” is a masterpiece of songwriting and performance, defying easy description. From its opening line, “It could all be so simple/ But you’d rather make it hard,” “Ex-Factor” encapsulates the pain, confusion, and naivete of a complex relationship. Hill’s vocal performance, shifting between ecstasy and yearning, is both powerful and vulnerable. Sampling Wu-Tang Clan’s “Can It Be All So Simple,” “Ex-Factor” is a song of profound soul and emotional depth, making any attempt to replicate it feel almost sacrilegious.
5. Santana feat. Rob Thomas, “Smooth” (No. 1, Hot 100)
Santana’s “Smooth,” featuring Rob Thomas, became a ubiquitous hit in 1999, sparking strong reactions both positive and negative. The song’s iconic guitar licks, Rob Thomas’s growling vocals, and memorable lyrics, like “Man, it’s a hot one,” became instantly recognizable. “Smooth” embedded itself deeply into the public consciousness, sparking memes and becoming a cultural touchstone. While some might remember Santana primarily for “that Rob Thomas song,” its massive success and enduring impact are undeniable.
4. Juvenile feat. Mannie Fresh & Lil Wayne, “Back That Azz Up” (No. 19, Hot 100)
Juvenile’s “Back That Azz Up,” featuring Mannie Fresh and Lil Wayne, is a social experience in song form, guaranteed to pack dance floors and ignite parties. The song’s 15-second string intro acts as an auditory alarm clock, signaling party time. Mannie Fresh’s production and Juvenile’s simple yet effective lyrics created a bounce classic that transcended regional boundaries. “Back That Azz Up” broke down regional walls in hip-hop, paving the way for post-regional styles and solidifying its place as a timeless party anthem.
3. Backstreet Boys, “I Want It That Way” (No. 6, Hot 100)
Backstreet Boys’ “I Want It That Way” became their signature song and a defining boy band classic. Despite peaking at No. 6, “I Want It That Way” transcended chart positions to become their biggest hit. From the opening guitar plucking, the song transports 90s babies back to their youth. Max Martin’s bombastic production, epic key changes, and the song’s baffling yet iconic lyrics, “I Want It That Way” remains an all-time pop staple, earning a record of the year Grammy nomination and solidifying its place in pop history.
2. TLC, “No Scrubs” (No. 1, Hot 100)
TLC’s “No Scrubs” became a public service announcement in song form, defining what a “scrub” is for a generation. This anthem of female independence, written by Kandi Burruss and Tameka “Tiny” Cottle, and produced by Kevin “She’kespere” Briggs, called out freeloading men with playful yet pointed lyrics. Briggs’ innovative production, blending acoustic guitar with a hip-hop beat, created a timeless sound. Lisa “Left Eye” Lopes’ iconic rap verse, featured prominently in the space-age music video, further cemented “No Scrubs” as a feminist anthem and a lasting pop classic.
1. Britney Spears, “…Baby One More Time” (No. 1, Hot 100)
Britney Spears’ “…Baby One More Time” is not just a career-making song; it is a watershed moment in pop music history. Max Martin’s minimalist yet maximalist production created a revolutionary sound, blending funk-pop with Swedish pop sensibilities. “…Baby One More Time” was a calculated and visionary debut, perfectly timed for a pop market hungry for a new icon. Spears’ blend of teenage naivete and Lolita coquettishness, combined with the iconic schoolgirl music video, captured the zeitgeist and launched a pop revolution. Twenty years later, the song’s iconic piano notes, Max Martin’s lasting impact on pop, and Britney’s enduring stardom all testify to the monumental impact of “…Baby One More Time,” the best song of 1999 and a defining track for millennial pop.
