31 Best Songs From 1999

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.

“Angel” By Sarah McLachlan

Song Year: 1999

There was a time before the ASPCA commercials when “Angel” was a radio hit. Today, we recognize the Sarah McLachlan track as a fundraiser tool to raise awareness and fight animal abuse. But in the scorching hot music year of 1999, “Angel” received just as much radio play as other smash hits.

“Steal My Sunshine” By Len

Song Year: 1999

One thing about music in 1999 was that it was a literal buffet of styles. That’s how we fell in love with “Steal My Sunshine.” The Canadian alternative rock band earned the song airplay time by getting it on the Go soundtrack.

It’s not easy to define the song. Is it alternative rock? Is it pop? Is it indie? Or dance? One thing’s for sure. It’s 1999.

“Got Your Money” By Ol’ Dirty Bastard Featuring Kelis

Song Year: 1999

This year was so saturated with musical variety even a founding member of the underground hip-hop group Wu-Tang Klan was making the rounds on the radio. Ol’ Dirty Bastard, affectionately referred to as ODB, was in jail at the time of the release, but that didn’t stop this collaboration with R&B star Kelis from reaching the top of the charts.

“Slide” By The Goo Goo Dolls

Song Year: 1999

Another 1990s alternative rock band that hit it big in the time of free music for all thank you, Napster is the Johnny Rzeznik fronted Goo Goo Dolls. The band earned radio play in the mid-90s for the hit alt-rock song “Name.”

The band earned even more recognition when their single from the City of Angels soundtrack, “Iris,” sat at the number one Billboard spot for a record 18 consecutive weeks. The follow-up single “Slide” from the album Dizzy Up The Girl was their second number-one hit and an early 1999 mega-hit.

“Goodbye Earl” By The Dixie Chicks

Song Year: 1999

An anthem still to this day, “Goodbye Earl” is a country song that makes you sing along even if you’re not a country music fan. The song was first recorded by the country band Sons of the Desert, but it wasn’t until the Dixie Chicks got ahold of it that the single took off.

Dennis Franz, famous for showing his butt on NYPD Blue, plays the doomed Earl in the song. And the band wisely changed its name to The Chicks in later years.

“Tell Me It’s Real” By K-Ci & JoJo

“Tell Me It’s Real” By K-Ci & JoJo

Song Year: 1999

K-Ci & Jojo earned music credibility in the early nineties as members of the R&B group Jodeci. In the summer of 1999, the duo’s sophomore album It’s Real peaked at number two on the Billboard Top 100. And it was largely due to this summer R&B hit.

“Save Tonight” By Eagle Eye Cherry

Song Year: 1999

Eagle Eye Cherry was destined for success. His father is an American jazz musician. And his mother is a Swedish artist. Even his half-sister is Neneh Cherry. “Save Tonight” was a Top 10 US hit and was voted Song of the Year in New Zealand. Now, that’s what I call music.

“Summer Girls” By LFO

Song Year: 1999

If Abercrombie & Fitch wasn’t famous before this LFO single, it was after “Summer Girls.” And the Lyte Funky Ones followed this house party jam with the Jennifer Love-Hewitt pop song “Girl on TV.” It’s more than okay to sing along with LFO. Just keep an eye on your girl when the trio is around., especially if you have ever had your bike stolen.

“All-Star” By Smash Mouth

Song Year: 1999

Like “Angel” before it, “All-Star” became famous later for another reason. That reason is because of a famous movie released in 2001 called Shrek. In fact, at this point, the song should open with Mike Myers shouting, “What are you doing in my swamp?!?”

“Mambo No. 5” By Lou Bega

Song Year: 1999

Ladies and gentlemen, another smash hit from a one-hit-wonder. Only 1999 could turn “Mambo No.5” into a chart-topping number-one hit around the world. The song would become a staple at every wedding reception. It was so popular even Bob the Builder covered it for his 2001 debut album. True story.

“I Want It That Way” By The Backstreet Boys

Song Year: 1999

You can call them the original boy band. Nick, Howie, AJ, Brian, and Kevin started the wave that N’Sync, 98 Degrees, and LFO would ride into the next millennium. Haters are gonna hate but watch the mood in the room lift the moment “I Want It That Way” comes on the radio. That’s all the evidence you need for a certified banger.

“Back That A** Up” By Juvenile

Song Year: 1999

Okay, sure. The radio-edited version of “Back That Thang Up” doesn’t have the same appeal as the explicit version. But Juvenile still aggravated parents with this inappropriately fun hip-hop hit nonetheless.

The top ten hip-hop and rap song broke the Billboard Top 20. And it even introduced the world to Lil’ Wayne. Thank you for that, Juvenile. Surprisingly, he did not catch lightning in a bottle a second time with his 2021 release, “Vaxx That Thing Up.”

“Hard Knock Life Ghetto Anthem’” By Jay-Z

Song Year: 1999

Try getting this catchy beat out of your head after you hear it. For this hit, Jay-Z sampled a song from the 1970s Broadway stage play Annie, of all things. And it was a massive hit. “Hard Knock Life” peaked on the Billboard charts at number 15.

In March of ’99, it was certified gold and earned Jay-Z a Grammy nomination for Best Rap Solo Performance. And that was just one of Jay Z's legendary catalog of hit songs.

“Genie in a Bottle” By Christina Aguilera

Song Year: 1999

Whatever The Mickey Mouse Club was doing, it worked. Not only did they give the world Britney Spears and Justin Timberlake, but they also introduced us to the international sensation and host of the hit television show The Voice.

“Genie in a Bottle” as a single went double platinum. And it launched the very successful career of one of the greatest voice talents on Earth.

“Gotta Man” By Eve

Song Year: 1999

The first lady of the Ruff Ryders splashed onto the scene with a Billboard Top 40 hit that used a nursery rhyme for a chorus. It was the end of the millennium. Anything was possible. With a rap stable that included megastar DMX, Eve had big shoes to fill. “Gotta Man” proved why she was the boss.

“Every Morning” By Sugar Ray

Song Year: 1999

Sugar Ray titled their 1999 sophomore album 14:59 as they assumed their fifteen minutes of fame were up. They could not have been any more wrong. “Every Morning” tore up the charts to land at number three on the Billboard Hot 100. That 14:59 album would end up as a certified triple platinum album. And Mark McGrath would go on to co-host the TV show Extra.

“Nookie” By Limp Bizkit

Song Year: 1999

Limp Bizkit started as an underground band that rose to prominence as an opener for the well-established Korn band. However, they wanted to build their own identity. Combining provocative song and album names as well as performing aggressively and unapologetically, they managed to garner a lot of heat from the critics and interest from the music fans.

“Nookie” perfectly portrays just how wacky some of this band’s songs were. The title came to be on accident, as the guitarist Wes Borland jokingly suggested it after seeing the word on the cover of a porn magazine.

According to Fred Durst, the band’s lead singer, the song is about an exploitative girlfriend who was using him. Ultimately, he concluded that he was unable to leave her because of the nookie.

“Kiss Me” By Sixpence None The Richer

Song Year: 1999

In the year of musical inclusion, Sixpence None the Richer hit paydirt. Believe it or not, “Kiss Me” was written and performed by a Christian pop-rock band. This list includes pop songs, boy bands, country music, hip-hop, R&B, and alt-rock. It also includes mainstream Christian pop-rock hits. What a year.

“Better Off Alone” By Alice Deejay

Song Year: 1999

Break out your glow sticks. Get your candy pacifiers and lace your face masks with Vicks VapoRub, it’s time to rave! Considered a Eurodance techno-pop club track, “Better Off Alone” sold over a million copies worldwide. And it is one of the best 90s dance songs.

The song makes you want to find the first abandoned warehouse and throw an all-night underground dance party.

“Californication” By The Red Hot Chili Peppers

Song Year: 1999

Red Hot Chili Peppers released many great songs in the 90s, but there was something special about their 1999 Californication album. Produced by legend Def Jam co-founder Rick Rubin, Californication celebrated the return of guitarist John Frusciante, after Dave Navarro left the band in 1998.

The album included six hit singles, including the title track “Californication.” That song has an unbelievable one billion YouTube views. And it proves that 1999 was a great one for the Red Hot Chili Peppers. Except, of course, when they closed out Woodstock 99. But that’s another story for another day.

Top Songs From 1999, Final Thoughts

From pop to country and hip-hop to alternative rock, 1999 was the year of the crossover. In addition, arguably, some of the greatest hits of the past few decades were released that year.

So whether it’s hearing how Britney Spears introduced herself to the world or Lou Bega called us to the dance floors like no other, pick your favorites from our list and enjoy the plethora of top songs from 1999.

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