31 Best Songs From 1999

There’s not a 90s playlist more fun and eclectic than one packed to the rafters with hits from the end of the millennium. This list showcases some of the best songs from 1999. And now it’s time to party like it’s… 1999.

“…Baby One More Time” By Britney Spears

Song Year: 1999

Britney is more than a singer. She is a pop culture phenomenon. Remember when we thought she married George Costanza in Las Vegas? And then Britney married K Fed. She taught us the meaning of the word conservatorship. And we learned to leave Britney Alone.

This track was her debut single. It topped the charts in ten countries, including the US, Australia, the UK, and France. The album of the same name is certified 14x Platinum – also called Platinum. With over 25 million worldwide sales, “…Baby One More Time” is a guaranteed crowd-pleaser anywhere on the planet.

“Believe” By Cher

Song Year: 1999

Don’t call this a comeback. The Goddess of Pop returned to music with her first Platinum album in a decade. “Believe” is a pulse-pounding, funky pop techno track that introduced Cher to a new generation of disciples. There wasn’t a Top 40 radio station that wasn’t pumping out “Believe” on the hour back in ‘99.

“All the Small Things” By Blink 182

Song Year: 1999

Enema of the State was released in June of ’99 and put Blink 182 on the map. Hits like “What’s My Age Again?” and “Adam’s Song” made the pop-punk band famous. Or maybe it is that album cover with 1990s adult film star Janine Lindemulder dressed as a sexy nurse that did the trick. Either way, Blink 182 exploded in 1999 and is still a popular touring band in America.

“Smooth” By Santana Featuring Rob Thomas

Song Year: 1999

The Santana Blues Band was formed in San Francisco in 1966. But in 1999, their smash hit album Supernatural went 15x Platinum and topped the charts everywhere. There wasn’t a car stereo with a detachable face or a five-disc changer that didn’t have Santana’s Supernatural CD loaded in it.

Supernatural featured guest artists Eric Clapton, CeeLo Green, Dave Matthews, and Wyclef Jean. But Santana’s collaboration with Rob Thomas of Matchbox Twenty called “Smooth” blazed the charts throughout the year.

“Livin’ La Vida Loca” By Ricky Martin

Song Year: 1999

Upside, inside out. Music fans spent a wild ’99 collectively Livin’ La Vida Loca and loving every minute of it. Ricky Martin took home five MTV Music Awards. He was nominated for four Grammy Awards, including Record of the Year and Song of the Year. In addition, Puss and Donkey brilliantly covered the song in Shrek 2.

“Say My Name” By Destiny’s Child

Song Year: 1999

Destiny’s Child became a supergroup courtesy of this 1999 mega-hit. The group featured a talented trio of Beyonce, Kelly Rowland, and Michelle Williams. Beyonce, in particular, went on to become one of music’s biggest stars as a solo artist. She married another 90s chart-topper named Jay-Z in 2008. Together, the power couple is worth a billion dollars.

“No Scrubs” By TLC

Song Year: 1999

TLC put out smash hit after smash hit throughout the decade. Their first album includes the hits “What About Your Friends?” and “Baby, Baby, Baby.” Their next album CrazySexyCool added to their success with the hits “Creep” and “Red Light Special.”

Notably, 1999’s FanMail was the group’s first number-one album on the Billboard charts, thanks to the success of “No Scrubs.” Unfortunately, the early death of Lisa “Left Eye” Lopes would deprive us of more TLC super-hits.

“Man! I Feel Like A Woman” By Shania Twain

Song Year: 1999

Ninety-nine was the year of the crossover. Top 40 stations played pop tunes, rock songs, techno beats, hip-hop tracks, and even country music. Generations of music fans patiently waited for a time when all genres were equal. And in 1999, it looks like we made it.

Country superstar Shania Twain was a mainstream artist in 1999. Her album Come On Over churned out hits like “Man! I Feel Like A Woman”. And Shania Twain is still the only female artist to sell over 40 million albums.

“Jumper” By Third Eye Blind

Song Year: 1999

By the end of 1999, was it even considered “alternative” rock if it was all over the radio? Third Eye Blind was a staple of the American Pie generation. Gen X kids filled outdoor concert festivals and packed themselves together to crowd surf and mosh to the songs of Third Eye Blind. Their hit “Jumper” was one of those mosh hit classics.

“Doo Wop” That Thing” By Lauryn Hill

Song Year: 1999

The Fugees were a phenomenon. But when Lauryn Hill released her debut album as a singles artist, she changed the world.

In the first week of its release, The Miseducation of Lauryn Hill broke the record for most album sales by a female artist. And in 1999, she took home five Grammy Awards, including Album of the Year.

Who needs Pras and Wyclef when you’re on top of the world? “Doo Wop” is a perfect 1999 track to pump any music fan.

“Wild Wild West” By Will Smith

Song Year: 1999

It was a forgettable movie, admittedly. But that banger from the Fresh Prince and the guy who sang “The Thong Song” was lit. In hindsight, was it that good? Maybe we loved “Wild Wild West” because we were still living off the fun of “Men in Black.” Oh, well. It’s still fun to sing along to that sick Sisqo hook.