1999 in Review: 25 Songs Everyone Was Listening to 25 Years Ago

America was at a crossroads in 1999—which might explain why music fans were split between listening to sugary teen-pop and angry nu-metal.
TLC in 1999.
TLC in 1999. / Jeffrey Mayer/WireImage via Getty Images

In 1999, the final year of the 20th century, America was at a crossroads. While the nation was still enjoying the unprecedented peace and prosperity of the late ’90s, anxiety related to the dreaded Y2K bug had many people fearing armageddon was imminent. Nobody could tell if it was the best of times or the end of times—which might explain why sugary teen-pop and angry nu-metal were two of the biggest sounds around.

But that’s not all people were rocking out to as the millennium approached. What follows is a list of 25 songs turning 25 in 2024. It’s a testament to the wonderful weirdness of 1999, the year that gave us indelible hits by Limp Bizkit, Christina Aguilera, Macy Gray, and of course, Lou Bega.

1. Blondie // “Maria”

Blondie’s first single since 1982 was a real doozy. In the UK, where the New York City rockers had always been huge, the song reached No. 1, making Blondie the first and only American act to top that country’s charts in the ’70s, ’80s, and ’90s. “Maria” also made Blondie singer Debbie Harry, then 53, the oldest woman to have a No. 1 UK hit. (Cher had been slightly younger when she reached the summit with “Believe” the previous year.)

2. TLC // “No Scrubs”

“No Scrubs” gave TLC their third No. 1 hit on the Billboard Hot 100—and the song’s lyrics, all about broke dudes catcalling women from passing cars, put some men on the defensive. The New York City rap group Sporty Thievz even scored a Top 20 smash with their answer record, “No Pigeons.”

3. Eminem // “My Name Is”

Produced by Dr. Dre, Eminem’s tongue-in-cheek breakthrough single, “My Name Is,” samples British singer-songwriter Labi Siffre’s 1975 tune “I Got The …” Siffre refused to clear the sample until Eminem agreed to cut some of the song’s homophobic lyrics.

4. Britney Spears // “... Baby One More Time”

Although it was technically released in late 1998, Britney Spears’s world-beating debut single, “... Baby One More Time,” remained massive throughout the following year. It topped the Billboard Hot 100 in January of ’99, and Billboard later ranked it the fifth biggest song of the year. And to think, songwriter Max Martin originally intended the tune for TLC.

5. Tom Waits // “Hold On”

Despite his craggy voice and penchant for bizarre storytelling, Tom Waits can make beautiful songs when he wants to. His acclaimed 1999 album Mule Variations includes “Hold On,” an optimistic song of romantic resilience written with his wife, Kathleen Brennan. “Hold On” earned Waits a Grammy nomination for Best Male Rock Vocal Performance. He lost to Lenny Kravitz.

6. Ricky Martin // “Livin’ La Vida Loca”

The chart-topping breakthrough single for Puerto Rican heartthrob and former Menudo member Ricky Martin, which was completely inescapable in the summer of 1999, holds the distinction of being the first U.S. No. 1 hit recorded entirely with the digital audio workstation Pro Tools. That said, “Livin’ La Vida Loca” does feature some real instruments, including horns and acoustic guitar.

7. Shania Twain // “Man! I Feel Like a Woman!”

Shania Twain’s gargantuan third album, Come On Over, dropped in 1997, but it kept spinning off singles into the new millennium. The most enduring of these may be “Man! I Feel Like a Woman!”, a strutting country-rock female-empowerment jam with a chorus that’s meant to be screamed at the top of your lungs.

8. Blink-182 // “What’s My Age Again?”

Originally titled “Peter Pan Complex,” the gleefully immature breakout single for San Diego punk-rock goofballs blink-182 was born from a mistake. Bassist Mark Hoppus was trying to play Green Day’s “J.A.R.” on guitar, and he accidentally came up with the now-familiar intro riff to “What’s My Age Again?”

9. Jennifer Lopez // “If You Had My Love”

J. Lo came strong out of the gate with her debut single, “If You Had My Love,” which spent five weeks atop the Billboard Hot 100. Shortly before the song dropped, Michael Jackson heard producer Rodney Jerkins’s demo and nearly opted to record it himself. Fortunately for Lopez, the King of Pop thought it would sound better with a female singer. 

10. Ja Rule // “Holla Holla”

In the early 2000s, Ja Rule became a pop-rap titan with radio-ready jams like “Livin’ It Up” and “Always on Time.” But the NYC rapper actually came on the scene with 1999’s “Holla Holla,” a last-minute addition to his debut album, Venni Vetti Vecci. Def Jam had been asking for a hit single, and Ja delivered, cracking the Top 40 and setting the stage for future triumphs.

11. Smash Mouth // “All Star”

With “All Star,” Smash Mouth avoided the curse of being a one-hit wonder (let us not forget 1997’s “Walkin’ On the Sun”) and gave the world a perennial sports anthem, which is funny, since it was written by guitarist Greg Camp, the only member of Smash Mouth not into sports. Smash Mouth even performed “All Star” at the 1999 Home Run Derby at Fenway Park.

12. Red Hot Chili Peppers // “Scar Tissue”

The lead single from the seventh Red Hot Chili Peppers album features music by guitarist John Frusciante—his first after coming back in the fold after a six-year absence. Upon hearing the guitar riff, lead singer Anthony Kiedis immediately connected with the “playful, happy-to-be-alive, phoenix-rising-from-the-ashes vibe” and penned lyrics to match. The song became the group’s first Top 10 pop hit since 1991.  

13. Lit // “My Own Worst Enemy”

Lit frontman A. Jay Popoff told SPIN magazine that he sang “My Own Worst Enemy,” his band’s punky, poppy 1999 breakthrough smash, naked in the studio. This would be weirdly appropriate, given that it’s a song about getting loaded and acting a fool. 

14. Santana featuring Rob Thomas // “Smooth”

When Rob Thomas sang, “Man, it’s a hot one,” the famous opening line of this Latin-rock earworm, he might as well have been talking about this song itself. “Smooth” spent 12 weeks atop the Billboard Hot 100, reignited the career of Carlos Santana, and dominated radio in the closing months of the second millennium. It’s hard to imagine anyone but Thomas singing it, but he actually co-wrote it with George Michael in mind.

15. Limp Bizkit // “Nookie”

On the strength of this brutish kissoff—perhaps the most famous song of the nu-metal era—Limp Bizkit’s 1999 sophomore album, Significant Other, reached No. 1 on the Billboard 200. It’s among the tunes the band played during their infamous Woodstock ’99 set.

16. Macy Gray // “I Try”

Macy Gray’s one and only pop hit, the deceptively perky soul-pop heartbreaker “I Try,” almost didn’t reach the mass audiences it deserved. Gray fought with her label over the song, insisting it shouldn’t be a single. Thank goodness she lost that fight.

17. Destiny’s Child // “Say My Name”

Saying the names of the members of Destiny’s Child was a little tricky circa “Say My Name,” the group’s second No. 1 hit. Though the song includes vocals from Beyoncé, Kelly Rowland, LeTavia Roberson, and LeToya Luckett, the music video features Bey, Rowland, and the two singers who replaced Roberson and Luckett: Michelle Williams and Farrah Franklin. Roberson and Luckett claimed they didn’t know they’d been fired until they saw the video.

18. Christina Aguilera // “Genie In a Bottle”

The teen-pop era reached its peak in 1999, and Christina Aguilera notched a No. 1 hit with this suggestive lead single from her self-titled debut album. But Aguilera wasn’t interested in being a typical pop star—she fought to infuse her songs with more R&B flavor—and with subsequent LPs, she inserted more of her own personality into the mix. 

19. LFO // “Summer Girls”

Part nostalgic love song, part barrage of unrelated pop culture references, “Summer Girls” is a strangely sweet pop-rap confection that somehow never loses its charm. Sadly, LFO frontman Rich Cronin died of leukemia in 2010, followed by bandmate Devin Lima in 2018 and Brian Gillis in 2023.

20. Lou Bega // “Mambo No. 5 (A Little Bit Of…)”

Though tangentially related to both the ’90s swing revival and the Latin-pop boom, “Mambo No. 5” was very much its own thing. German-born singer Lou Bega based the retro-leaning smash (his lone American hit) on a sample from Cuban bandleader Pérez Prado’s 1949 chestnut “Mambo No. 5.” Bega’s big contribution was adding lyrics—most notably a hyper-catchy chorus that calls out nine different women: Pamela, Angela, Monica, Erica, Rita, Tina, Sandra, Mary, and Jessica.

21. Ol’ Dirty Bastard // “Got Your Money”

Produced by Pharrell and Chad Hugo, a.k.a. the Neptunes, “Got Your Money” became Wu-Tang Clan eccentric Ol’ Dirty Bastard’s first and only Top 40 pop hit as a lead artist. ODB gets some help on the hook from singer Kelis, later of “Milkshake” fame, who assures him that, yes, she’s got his money—no need to worry.

22. Len // “Steal My Sunshine”

Perfectly engineered for summer parties, “Steal My Sunshine” was born early one morning while Len frontman Marc Costanzo was partying at a rave in his hometown of Toronto. He wrote the lyrics on his leg and on a napkin, and if you’re of a certain age, you probably know these words by heart.

23. Dr. Dre // “Still D.R.E.”

Dr. Dre’s big 1999 comeback single features lyrics ghostwritten by none other than Jay-Z. According to Dre, it took Jay a few minutes to get into the West Coast mindset, but once he did, the Brooklyn legend wrote the whole song—including guest Snoop Dogg’s parts—in 20 minutes.

24. Backstreet Boys // “I Want It That Way”

Swedish pop songsmith Max Martin has a questionable command of the English language—hence the head-scratching lyrics of this 1999 boy-band classic—but there’s no doubting his way with a melody. Teen pop arguably never got better than this.

25. Sugar Ray // “Every Morning”

Sugar Ray gave the world a handful of perfect pop singles, and “Every Morning” might be the best of the bunch. Mark McGrath and the gang based part of the chorus on the Latin-rock band Malo’s 1972 tune “Suavecito,” a staple of lowrider car shows in Sugar Ray’s native Southern California.