Buzz
The final year of the 20th century, 1999, found America at a pivotal moment. While the country continued to ride the wave of peace and prosperity that marked the late ’90s, the looming threat of the Y2K bug cast a shadow of fear about the future. People couldn’t decide if it was the peak of an era or the beginning of its end—which could explain why pop music with catchy hooks and angst-fueled nu-metal dominated the airwaves.
But music wasn’t limited to just those two genres as the millennium drew closer. Below is a list of 25 tracks celebrating their 25th anniversary in 2024, showcasing the delightful and strange musical landscape of 1999. This was the year that brought us unforgettable hits from artists like Limp Bizkit, Christina Aguilera, Macy Gray, and the inescapable Lou Bega.
1. Blondie // “Maria”
Blondie made a major comeback with their first single in 17 years, and it was a hit. In the UK, where the New York band had always been beloved, “Maria” climbed straight to No. 1, making Blondie the only American act to top the charts in the ’70s, ’80s, and ’90s. The track also made Debbie Harry, at 53, the oldest woman to achieve a No. 1 hit in the UK (Cher had been a bit younger when she reached the top with “Believe” the year before).
2. TLC // “No Scrubs”
With “No Scrubs,” TLC scored their third No. 1 on the Billboard Hot 100. The song, which calls out men who try to hit on women while lacking any real ambition, sparked some controversy. The New York rap duo Sporty Thievz even released a response track, “No Pigeons,” which landed in the Top 20.
3. Eminem // “My Name Is”
Produced by Dr. Dre, Eminem’s breakthrough track “My Name Is” featured a cheeky sample of Labi Siffre’s 1975 song “I Got The ….” Siffre initially refused to clear the sample until Eminem agreed to alter some of the song’s more controversial, homophobic lyrics.
4. Britney Spears // “...Baby One More Time”
Though technically released in late 1998, Britney Spears’ debut single, “...Baby One More Time,” remained a colossal hit well into 1999. The song topped the Billboard Hot 100 in January and was later ranked the fifth biggest song of the year by Billboard. Ironically, Max Martin, the song’s writer, had originally penned it for TLC.
5. Tom Waits // “Hold On”
Known for his gravelly voice and quirky, often surreal storytelling, Tom Waits proved he could craft beautiful songs when he put his mind to it. “Hold On,” from his acclaimed 1999 album *Mule Variations*, is a hopeful, resilient love song co-written with his wife, Kathleen Brennan. The track earned Waits a Grammy nomination for Best Male Rock Vocal Performance, though he ultimately lost out to Lenny Kravitz.
6. Ricky Martin // “Livin’ La Vida Loca”
Ricky Martin's chart-topping smash hit, “Livin’ La Vida Loca,” took over the summer of 1999 and marked the first U.S. No. 1 hit ever recorded entirely using the digital audio workstation Pro Tools. Despite the heavy use of digital technology, the track also includes some live instruments, including horns and acoustic guitar.
7. Shania Twain // “Man! I Feel Like a Woman!”
Though Shania Twain’s colossal third album *Come On Over* was released in 1997, its singles continued to dominate well into the next millennium. “Man! I Feel Like a Woman!” stands out as the most iconic, a fiery country-rock anthem of female empowerment with a chorus that begs to be belted at full volume.
8. Blink-182 // “What’s My Age Again?”
Originally called “Peter Pan Complex,” Blink-182’s breakout hit was a product of a happy accident. While bassist Mark Hoppus was attempting to play Green Day’s “J.A.R.” on guitar, he instead stumbled upon the now-famous opening riff of “What’s My Age Again?”
9. Jennifer Lopez // “If You Had My Love”
Jennifer Lopez made a bold debut with her first single, “If You Had My Love,” which spent an impressive five weeks at No. 1 on the Billboard Hot 100. Just before the song’s release, Michael Jackson heard a demo produced by Rodney Jerkins and nearly chose to record it himself. Ultimately, the King of Pop decided it was better suited for a female voice, a decision that worked out perfectly for Lopez.
10. Ja Rule // “Holla Holla”
In the early 2000s, Ja Rule would go on to dominate pop-rap with hits like “Livin’ It Up” and “Always on Time,” but his journey started with the gritty 1999 single “Holla Holla.” A last-minute addition to his debut album *Venni Vetti Vecci*, it was a response to Def Jam’s demand for a radio-ready single. Ja delivered, cracking the Top 40 and paving the way for his future success.
11. Smash Mouth // “All Star”
With “All Star,” Smash Mouth broke free from the one-hit wonder label (we all remember 1997’s “Walkin’ On the Sun”) and gifted us a timeless sports anthem. Ironically, the track was written by guitarist Greg Camp, the only member of the band who wasn’t really into sports. Smash Mouth even performed the song at the 1999 Home Run Derby at Fenway Park.
12. Red Hot Chili Peppers // “Scar Tissue”
The lead single from the Red Hot Chili Peppers’ seventh album marked the return of guitarist John Frusciante, whose music defined the track. After six years away from the band, Frusciante’s guitar riff immediately resonated with lead singer Anthony Kiedis, who captured the ‘phoenix-rising-from-the-ashes’ feeling in his lyrics. “Scar Tissue” went on to become the band’s first Top 10 hit since 1991.
13. Lit // “My Own Worst Enemy”
Lit’s breakout 1999 anthem “My Own Worst Enemy” was famously recorded with frontman A. Jay Popoff singing the track completely naked in the studio. According to Popoff, this seemed fitting for a song that explores themes of reckless behavior and self-destruction.
14. Santana featuring Rob Thomas // “Smooth”
When Rob Thomas belted out the iconic opening line, “Man, it’s a hot one,” in the Latin-rock hit “Smooth,” he could have easily been describing the track itself. This collaboration between Santana and Thomas spent an incredible 12 weeks at No. 1 on the Billboard Hot 100, revitalized Santana’s career, and dominated the airwaves as the millennium drew to a close. Though it’s hard to picture anyone but Thomas singing it, he actually co-wrote the song with George Michael in mind.
15. Limp Bizkit // “Nookie”
Limp Bizkit’s anthem “Nookie” — an angsty anthem of rejection and defiance — helped propel their 1999 album *Significant Other* to No. 1 on the Billboard 200. This track became synonymous with the nu-metal movement and was one of the standout songs during their infamous Woodstock ’99 performance.
16. Macy Gray // “I Try”
Macy Gray’s sole mainstream hit, the deceptively upbeat soul-pop ballad “I Try,” nearly missed out on the widespread success it went on to achieve. Initially, Gray fought with her record label, arguing that the song shouldn’t be a single. Thankfully, she lost that battle and the world was gifted with this unforgettable track.
17. Destiny’s Child // “Say My Name”
With “Say My Name,” Destiny’s Child scored their second No. 1 hit. However, the video’s lineup was a bit of a puzzle. Although Beyoncé, Kelly Rowland, LeTavia Roberson, and LeToya Luckett provided the vocals, the video featured just Beyoncé, Rowland, and the two replacements for Roberson and Luckett: Michelle Williams and Farrah Franklin. Roberson and Luckett later claimed they had no idea they were being replaced until they saw the final cut.
18. Christina Aguilera // “Genie In a Bottle”
1999 marked the peak of the teen-pop explosion, and Christina Aguilera’s breakout single “Genie In a Bottle” shot straight to No. 1. But Aguilera wasn’t interested in being another cookie-cutter pop star. She fought to give her music a more R&B flavor and, with future albums, made sure to infuse them with more of her personal style and voice.
19. LFO // “Summer Girls”
A quirky blend of nostalgic love song and a whirlwind of pop culture references, LFO’s “Summer Girls” is a pop-rap gem that somehow never loses its charm. Tragically, LFO frontman Rich Cronin passed away from leukemia in 2010, followed by bandmates Devin Lima in 2018 and Brian Gillis in 2023.
20. Lou Bega // “Mambo No. 5 (A Little Bit Of…)”
Though it ties into both the ’90s swing revival and the Latin-pop wave, Lou Bega’s “Mambo No. 5” carved its own unique lane. Based on a sample from Cuban bandleader Pérez Prado’s 1949 classic, Bega’s big contribution was adding his own lyrics, especially the irresistibly catchy chorus that names nine women: Pamela, Angela, Monica, Erica, Rita, Tina, Sandra, Mary, and Jessica.
21. Ol’ Dirty Bastard // “Got Your Money”
Produced by Pharrell and Chad Hugo, also known as the Neptunes, “Got Your Money” marked Wu-Tang Clan’s unpredictable Ol’ Dirty Bastard’s first and only Top 40 hit as the lead artist. He gets vocal assistance from singer Kelis, who would later rise to fame with “Milkshake,” assuring ODB that, indeed, she’s got his money—so there’s no need to stress.
22. Len // “Steal My Sunshine”
Perfectly suited for summer parties, “Steal My Sunshine” was born after a night of raving in Toronto, where Len frontman Marc Costanzo penned the lyrics on his leg and a napkin. If you grew up in the right era, these words are likely etched in your memory.
23. Dr. Dre // “Still D.R.E.”
Dr. Dre’s massive 1999 comeback hit features lyrics penned by none other than Jay-Z. Dre recalls that it took Jay a few moments to get into the West Coast vibe, but once he did, the Brooklyn legend cranked out the entire song, including Snoop Dogg’s verses, in just 20 minutes.
24. Backstreet Boys // “I Want It That Way”
Swedish hitmaker Max Martin may not have been fluent in English, which led to some curious lyric choices in this 1999 boy-band anthem. However, there’s no question about his mastery of melody. This song may just be the pinnacle of teen pop.
25. Sugar Ray // “Every Morning”
Sugar Ray delivered several perfect pop songs, but “Every Morning” stands out as perhaps their best. Mark McGrath and the band drew inspiration for part of the chorus from Malo’s 1972 hit “Suavecito,” a song that became a fixture at lowrider car shows in their native Southern California.
