This anthem called out guys who think they’re hot stuff just because they drive cars, leaving many men a bit embarrassed. For TLC, it was their third time hitting No. 1 on the Billboard charts.
Produced by Dr. Dre, "My Name Is" samples British singer-songwriter Labi Siffre’s 1975 track "I Got The...". Siffre only approved after Eminem agreed to remove some homophobic lyrics, showing respect and growth.
Though technically released late 1998, Britney’s debut hit stayed popular well into 1999, topping the Billboard Hot 100 in January and ranking as the year’s fifth biggest hit. Pure pop magic!
Puerto Rican heartthrob and former Menudo member Ricky Martin’s summer 1999 smash was the first American No. 1 fully recorded using Pro Tools digital software, yet it still features real horns and acoustic guitar. Talk about blending tech with soul!
Shania’s 1997 album Come On Over kept the hits coming into the new millennium. "Man! I Feel Like a Woman!" stands out as a bold country-rock anthem made for belting out at full volume.
Originally titled "Peter Pan Complex," this playful, immature tune was born from a happy accident when bassist Mark Hoppus tried to play Green Day’s "J.A.R." on guitar and stumbled upon the now-iconic intro riff.
With "All Star," Smash Mouth dodged the one-hit wonder curse (remember 1997’s "Walkin' On the Sun") and gifted the world a timeless sports anthem—ironically written by their only non-athlete member, guitarist Greg Camp. They even rocked it at the 1999 Home Run Derby at Fenway Park.
Lit’s frontman A. Jay Popoff told SPIN magazine he recorded "My Own Worst Enemy"—their 1999 punk-pop breakthrough—completely naked. Now that’s commitment to your art!
Thanks to this nu-metal anthem, Limp Bizkit’s 1999 album Significant Other hit No. 1 on the Billboard 200. "Nookie" was also part of their infamous 1999 Woodstock set—talk about making a statement!
While Beyoncé, Kelly Rowland, LaTavia Roberson, and LeToya Luckett all sang on the track, the video features Beyoncé, Rowland, and replacements Michelle Williams and Farrah Franklin. Roberson and Luckett claimed they didn’t know they’d been replaced until they saw the video—talk about drama behind the scenes.
The teen-pop era peaked in 1999 with Christina’s captivating debut single from her self-titled album. But she wasn’t content being a typical pop star—she fought to add more R&B flavor and reveal more of herself in later albums.
While touching on ’90s swing and Latin-pop waves, Lou Bega’s retro hit was uniquely his own. Inspired by Pérez Prado’s 1949 Cuban mambo, Bega added catchy lyrics naming nine different women—Pamela, Angela, Monica, Erica, Rita, Tina, Sandra, Mary, and Jessica—making it unforgettable.
Produced by Pharrell and Chad Hugo (The Neptunes), "Got Your Money" became Ol' Dirty Bastard’s only Top 40 pop hit. Kelis, future "Milkshake" star, lent her voice to reassure ODB that yes, she’s got his money—no worries.
Perfect for summer parties, "Steal My Sunshine" was born early one morning when Len’s frontman Marc Costanzo was partying at a rave in his hometown Toronto. He scribbled the lyrics on his foot and a napkin—now it’s a sing-along classic.
Swedish pop songwriter Max Martin doesn’t fully grasp English, which explains why some lyrics in this 1999 hit don’t always make perfect sense—but there’s no denying his knack for catchy melodies.
Sugar Ray gifted the world a handful of perfect pop hits, with "Every Morning" standing out. Mark McGrath and the band based part of the chorus on Malo’s 1972 Latin-rock classic "Suavecito," a staple at lowrider car shows in their Southern California hometown.
Once you hit a certain age, hearing “Who’s in the house?” will irresistibly make you shout back, “Kozmix in the house!” It’s a timeless call-and-response.
It’s almost unbelievable this song is already 25 years old. Since then, it’s been a staple at many weddings—probably enough time for some of those marriages to have run their course, too.
Is there a more life-affirming song about mortality? Among Kispál és a Borz’s many hits, this one is probably the most recognized—even by those who didn’t rock corduroy pants in high school.
With Cipő’s distinctive voice and Republic’s signature melodies, this song sounds upbeat, but its lyrics reveal the everyday struggles and pressures of the common person.
Tankcsapda’s album Ha zajt akartok! dropped in February 1999, delivering timeless tracks like "Mennyország Tourist" and "Üljenek a fiúk ölébe a lányok" that still resonate today.