1999 doesn't feel like it was 20 years ago. No one understands Y2K jokes anymore, Furbies are legitimate collector's items, and dial-up could legally be defined as a method of unlawful torture, but it's hard to believe the nineties are so far gone that next year, everyone born in that decade will be old enough to legally buy drinks. Whether you were a toddler, a teen, or a thirty-something during the last year of the century, you'll still remember these 1999 bops.
Shockingly, Smash Mouth is still a band, but they've never had a bigger hit than their number four Billboard Hot 100 chart almost-topper, "All Star." The song is still popular, mostly because of the movie Shrek, which is the most Y2K-era phenomenon we've ever heard. In 2017, the songwriter Greg Camp explained that the song is a social battle cry, a fanbase affirmation, a sports anthem, and poetically lyrical, which seems like a bit of a stretch, but it's definitely fun. It hit the top of the Mainstream Top 40 chart, so the people of the '90s agreed.
This is the song that gave the Backstreet Boys the title of the supreme boy band of the '90s, sorry Justin Timberlake stans. "I Want It That Way" is basically the Backstreet Boys signature song, and their all-white music video outfits as they danced in Tom Bradley International at LAX have gone down in pop culture history. It's why Rolling Stone called the Backstreet Boys the best boy band of all time, it was nominated for three Grammy Awards, and its been covered by Selena Gomez, One Direction, Brittney Howard, and Chance the Rapper.
This Billboard Hot 100 chart topper was one of the biggest songs of 1999 because, even then, Beyoncé could do no wrong. This was Destiny's Child's first number-one, the best-selling single of the year, and it was a crossover hit in the United Kingdom. The band wrote the song themselves (alongside two other co-writers), and the music video was set in a beauty salon as an homage to Tina Knowles, Beyoncé's mother and future fashion designer. The song didn't win either of the Grammy Awards it was nominated for, but it's still popular two decades later.
Ricky Martin might not be as big of a star in the USA as he once was, but the king of Latin pop had his first Billboard Hot 100 chart-topper with "Livin' la Vida Loca" from his first English-language album. The song is regarded as the beginning of the Latin pop explosion that brought Enrique Iglesias, Marc Anthony, and Sharika into the American charts after Ricky performed it at the 41st Grammy Awards. VH1 ranked it at 28th of the 100 Greatest Songs of the '90s, and it was Canada's top single of the year.
TLC had two top songs of 1999, "Unpretty" and "No Scrubs," and they both remain highly popular even in the 2010s. "No Scrubs" became one of TLC's biggest songs *ever* and was the second-biggest song of the year, behind only Cher's "Believe." It was their third number-one song and the first time that Chilli took the lead on a TLC single. The version with Left Eye's rap wasn't actually included on their album, but they had the good sense to make it the official single version of the song.
Mariah Carey and Jay-Z co-wrote "Heartbreaker," which Mariah also co-produced because once you hit your seventh studio album, you know what you want and how to get it. This was her second single that featured a rapper and marked her transition into the hip-hop and R&B market. It wasn't her most critically beloved song, but it was Mariah's fourteenth number-one hit. The music video was one of the most expensive ever created with a $2.5 million price tag and two Mariah Careys: one blonde, and one brunette. Both flawless.
Yes, "Mambo No. 5" has technically been around since the '50s, but Lou Bega's cover became the best-selling single of 1999 in Australia and a chart-topper in the United Kingdom before reaching the number-three position on the US charts. When you think "Mambo No. 5," you're definitely hearing Lou's voice in your head and not the earlier jive hit by Pérez Prado. Pérez's estate tried to sue Lou for sampling riffs from the original even though he re-wrote the lyrics entirely, which is totally legal in Lou's native Germany, but they ended up sharing writing credits.
Sony Music Entertainment
"She's So High" only reached 14th on the Hot 100 even though it made it to the number-one spot on the Adult Top-40, but it won a Juno Award in Tal Bachman's native Canada and a BMI award. The song is, surprisingly, not a metaphor for smoking weed. Tal explained to MTV News that the song was inspired by a conversation he had with the hottest girl in his high school while he was trying to bribe her to date his stepbrother. TBH, if I was this girl, I would have acted a little cold towards the freak trying to buy me for his relative, too.
"All The Small Things" didn't peak in popularity until after the start of the new millennium, but it was released in 1999 on Blink-182's third album, Enema of the State. Yes, the paradigm of 2000s teen movie soundtrack hits was actually released before people realized that the Millennium bug wasn't actually going to be that big of a deal. It's Blink-182's only song to break into the Top 40, which is crazy considering their enduring popularity. The music video parodied the biggest hits of '99 like "I Want It That Way" and hits from Britney and Christina, making it a true bridge between '99 and '00.
What? My name is... Who? This is probably better known today as the Slim Shady song, and Eminem did stand up when he accepted his first Grammy Award for Best Rap Solo Performance for "My Name Is" in 2000. The first track off of 1999's The Slim Shady LP was ranked one of the best hip hop songs of all time by Rolling Stone in 2016, nearly two decades after its release, and it was released by prolific rap artist Dr. Dre. The radio version is vastly different from the uncensored lyrics, so this could honestly be considered two different list entries.
Britney Spears was at the literal top of her game in 1999. A year before she would release Oops!... I Did It Again, Britney's first album ...Baby One More Time spawned two of the top songs of '99: the titular song from the album and "(You Drive Me) Crazy." This was also the beginning of Swedish producer Max Martin's dominance, who now has the third-most number-one singles on the Hot 100 after only Paul McCartney and John Lennon. You know, NBD.
While Britney was still clinging to her purity ring persona, her Mickey Mouse Clubhouse costar Christina Aguilera went the exact opposite route with *her* biggest song of '99, "Genie In A Bottle." The one where she asks her baby to "rub [her] the right way." Her debut album was released the same year as ...Baby One More Time, reinforcing a Britney vs. Christina feud that lasted throughout the first decade of their respective careers. "Genie In A Bottle" also hit the top of the charts and was the song of the summer. It was covered by Dove Cameron in 2016 for Disney Channel with family-friendly lyrics in some cosmic irony and Camila Cabello sampled it in her meme-ified hit "Crying in the Club" in 2017.
1999 was a *great* year for alternative artists. The Foo Fighters, aka Dave Grohl and those other guys, won a 2000 Grammy Award for Best Short Form Music Video for its Airplane! parody featuring Tenacious D. Sad to say a lot of twenty-somethings might mostly know this song from its appearance on the Rock Band video game in 2007, but it was the prolific band's first number one on the Modern Rock Tracks chart and their highest charting Hot 100 Airplay entry.
Remember when Will Smith was best known as a rapper? This '99 hit came out long after Will realized his passion for acting during The Fresh Prince of Bel-Air, which ended in 1996. His career as a movie star is one of the most successful in history, and "Wild Wild West" served as the lead single from his second album Willennium and a single from his $170 million-grossing film of the same name. The song topped the Hot 100 and had a seven-minute music video with appearances from Stevie Wonder and Enrique Iglesias.
"Believe" was the top song of 1999 off of Cher's twenty-second album Believe. That's right, her *twenty-second* album. If you've seen the Tony-nominated Cher Show on Broadway, you know Cher is the queen of hustle. It marked Cher's departure from pop rock into dance-pop and was one of the first deliberate uses of Auto-Tune to create a noticeable distortion. Cher became the oldest female solo artist to top the Hot 100, the song became the highest-selling single by a solo female artist in the U.K., and it was a major comeback by an artist that will never stay down.
Although "Jumper" was recorded in 1996, it wasn't released until late 1998 and didn't actually gain notoriety until 1999, meaning this is the 20th anniversary of people actually knowing who Third Eye Blind is. It was the final single from their self-titled debut and reached number five on the Hot 100, where it stayed long enough to become one of the biggest songs of 1999. The song is completely a depressing story about a gay man committing suicide, according to the band's lead singer Stephan Jenkins, but he's also said that the song has become less dark live in concert as it's been reclaimed by fans.
The Miseducation of Lauryn Hill remains one of the most stunning debuts from a rapper, earning Lauryn Hill ten Grammy nominations and five awards, the first woman to receive that number of accolades from the Recording Academy in one night. "Ex-Factor" was the second single from that album, an R&B, hip-hop, and soul hybrid that samples "Can It Be All So Simple" by the Wu-Tang Clan. It was solely written and produced by Lauryn and is her biggest UK hit, although her previous single "Doo Wop (That Thing)" performed better stateside.
The crazy thing is, the original version of "I Will Remember You" was released in 1995, where it only reached number 65 on the US charts. This 1999 version was a live recording from her album Mirrorball, a compilation of songs from her Surfacing tour in '97 and '98. For some reason, the live recording peaked at number 14, was certified Gold, and got Sarah McLaughlin her second Grammy Award. It was used for the Emmy Awards in memoriam ten years later but is best known by cable subscribers who have had to watch the torturous ASPCA commercials where it plays while sad animals stare at you.
Cash Money Records
An oldie but a goodie, people still get hype when "Back That Azz Up" gets played at clubs. Cash Money Records has been killing the game for nearly three decades, but the label was still fairly young when Juvenile, Mannie Fresh, and the future flagship artist of the company Lil Wayne, who was only nineteen at the time, released this. Weirdly enough, it only peaked at number nine on the Hot 100 and wasn't even Juvenile's best performing song, but "Back That Azz Up" proved itself through the test of time.
Before there was Taylor Swift or Kelsea Ballerini, Shania Twain was the one true queen of country pop. She remains the best-selling female artist in country music history and one of the best-selling artists literally ever. "Man! I Feel Like a Woman!" only peaked at number 18 on the Hot 100 and number two on the country charts, paling in comparison to "That Don't Impress Me Much," "You're Still The One," and her hits from the '00s, but it might be her most enduring country crossover hit. Even then, the song has been certified Platinum and won Shania a Grammy Award.