Do You Remember These Iconic Albums From 1999?

Let’s take a trip back to 1999. MySpace (a.k.a. the original Facebook) was just launched, Friends was the number one show in America, people were beginning to freak out about Y2K, and the black market music service Napster had taken over the web.

Luckily for Napster, there was a ton of new music being released in 1999 for teenagers all over America to illegally download. It’s hard to believe it’s been over twenty years since we first heard these iconic albums. Read on and see if you remember all the boy bands, pop princesses, Latin flare, and electronica from 1999.

Who could forget about the two pop princesses who battled it out at the Grammy’s with their 1999 debut albums?


1999 albums 1

The release of TLC’s fourth studio album came after a lot of drama. In 1995 they filed for bankruptcy, ended up in a huge legal feud with their music label, and the three members with fighting constantly. Still, they set out and released FanMail in February 1999.

FanMail is best known for giving us the song “No Scrubs” and being Lisa “Left Eye” Lopez’s last album. The album debuted at number one, was certified six-times platinum, and won the group three Grammy awards.

Backstreet Boys—Millennium

1999 albums 2

The ’90s was the decade of boy bands and with their third studio album, the Backstreet Boys gave a nod to the next 1000 years. Millennium included some of the Backstreet Boys’ greatest hits like “I Want It That Way” and “Larger Than Life.”

The album sold 30 million copies worldwide and their all-white outfits were cemented in history. Today, the Backstreet Boys have reunited and will kick off their DNA World Tour nearly twenty years to the date Millennium was released.

Jennifer Lopez—On The 6

1999 albums 3

By 1999, Jennifer Lopez had already established herself as the highest-paid Latina actress in the United States. She released her debut album on June 1, 1999. On The 6 was packed with singles that would go on to be iconic Latin-pop songs like “Waiting For Tonight,” “If You Had My Love,” and “Let’s Get Loud.”

While the album was only moderately successful, it allowed Jennifer to release her sophomore album two years later which would cement her as a Latin pop icon.

One of the hits from an album coming up is better known to kids as “the song from Shrek.”

Blink-182—Enema Of The State

1999 albums 4
Frank Micelotta/ImageDirect/Getty Images

The quirky pop-punk group had already released two albums before dropping their 1999 album Enema of the State. The first two albums built them a small but devoted following. In 1999, with singles like “What’s My Age Again,” “All The Small Things,” and “Adam’s Song,” Blink-182 became the biggest punk group at the turn of the millennium.

The band’s fame was heightened with their hilarious music videos which poked fun at the boy band phase of the time.

Sugar Ray—14:59

1999 albums 5

The Orange County band had formed more than a decade before the 14:59 album was released. Before 1999, their only major hit to date was “Fly” from two years before. Many critics claimed “Fly” was just a one-hit-wonder.

Tracks like “Every Morning” and “Someday” from the 14:59 album proved that the reggae-inspired pop band had more staying power. It even landed them a spot performing at the Woodstock 99 festival.

Smash Mouth—Astro Lounge

1999 albums 6
Bob Berg/Getty Images

Even though it was Smash Mouth’s second album, the release of Astro Lounge on June 8, 1999, was different from their previous music. It had more of a pop influence than ska, which led their singles to be played by more mainstream music stations.

Astro Lounge was critically acclaimed but supported by songs like “The The Morning Comes” and “All Star” which, of course, was featured two years later in the movie Shrek.

Coming up, the success of this pop star’s debut album left us asking her to hit us one more time with another record.

Eminem—The Slim Shady LP

1999 albums 7
Sal Idriss/Redferns/Getty Images

The Slim Shady LP was Eminem’s second album but first major-label debut. Released February 23, 1999, the album was written from Eminem’s alter ego Slim Shady and featured much more violent lyrics.

Despite the parental warnings, the main single “My Name Is” managed to make its way onto mainstream radio and the music video was a mainstay on MTV. The album sold more than 5 million copies and stayed on the Billboard charts for 100 weeks.

Mariah Carey—Rainbow

1999 albums 8
Kevin Mazur/WireImage/Getty Images

While Mariah Carey was already a certified female powerhouse in music by 1999, the release of her seventh studio album saw her take more creative control. For Rainbow, Mariah worked closely with new producers and musicians like Jay-Z, Snoop Dogg, and Usher.

Even though it was a turning point for her, Rainbow was Mariah’s lowest-selling album at the time. Still, we’d be lying if we said we weren’t still jamming to “Heartbreaker” from Rainbow.

Britney Spears—…Baby One More Time

1999 albums 9

Britney burst onto the scene early in 1999 with the release of her debut album, …Baby One More Time. The album featured some of her most memorable hits like “(You Drive Me) Crazy” and of course the title track.

Not only was the album iconic and cemented Britney’s place in pop history but to this day, it’s still one of her more successful albums and with 25 million copies sold, one of the best selling albums of all time.

Keep reading to see which fellow pop star’s album was Britney’s biggest competition.

Destiny’s Child—The Writing’s On The Wall

1999 albums 10
Michael Crabtree/PA Images/Getty Images

The Writing’s On The Wall was only the R&B girl group’s second studio album but it gave us some of their early memorable hits. Songs like “Bills, Bills, Bills,” “Jumpin, Jumpin, and “Say My Name” worked well with the wave of feminism sweeping through Hollywood at the turn of the century.

Destiny’s Child took more creative control over the 1999 album and it paid off. The Writing’s On The Wall earned them six Grammy nominations and went eight times platinum.

Red Hot Chili Peppers—Californication

1999 albums 11

The seventh studio album by Red Hot Chili Peppers is seen by many of their fans as their return to their roots. Guitarist John Frusciante returned to the band and is credited with completely changing their style of music.

Californication is much more mellow and relaxed than the band’s previous albums, but at the turn of the millennium, it somehow worked. Songs like “Scar Tissue,” “Otherside,” and “Californication” are still major hits today.

Christina Aguilera—Christina Aguilera

1999 albums 12
Scott Gries/Image Direct/Getty Images

The other pop princess of the ’90s released her debut album the same year as her fellow former Mouseketeer, Britney Spears. Christina’s album featured equally iconic hits like “What A Girl Wants” and “Genie In A Bottle.” Selling more than 14 million copies worldwide, it’s Christina’s best-selling album.

The album notably left Christina to square up against Britney at the 2000 Grammy Awards. Both women’s debut albums got them nominated for Best New Artist but it was Christina who won.

Britney and Christina may have dominated in 1999 but there were still quite a few pop singers who tried to take the crown.

Jessica Simpson—Sweet Kisses

1999 albums 13

It might not be on the same level as other heavyweight albums from 1999, but Jessica Simpson’s debut album was a big deal back in 1999. Singles like “I Wanna Love You Forever” and “I Think I’m In Love” had mixed critical reception but were certified as first-dance songs at everyone’s weddings in 2000.

The debut album did place the sweet Christian blond singer on Nick Lachey’s radar, which led to their marriage and one of the best/worst reality shows of the 2000s.

Mandy Moore—So Real

1999 albums 14
Steve Azzara/Corbis/Getty Images

Before she was making us cry on This Is Us, Mandy Moore was making us giggle with her bubblegum pop songs like “Candy” and “So Real.” While the album did well commercially, it couldn’t compete with other debut albums from female teen singers at the time like Britney Spears and Christina Aguilera.

While Britney and Christina embarked on their own tours, Mandy was stuck opening for boy bands like Backstreet Boys and NSYNC.

S Club 7—S Club

1999 albums 15
Tom Roney/Getty Images

Deny it all you want, but everyone in 1999 knew the words to every single from S Club 7’s debut album. Tracks like “Bring It All Back” and “S Club Party” were the go-to songs to dance to in your basement.

The success of S Club was helped along by the pop group’s television show Miami 7 which featured a lot of their songs. At one point the British pop group was even labeled “The Monkees for the next generation.”

Ricky Martin—Ricky Martin

1999 albums 16
Sam Levi/WireImage/Getty Images

The 1999 self-titled album was the Puerto Rican singer’s fifth studio album but it was only his third marketed in the United States and his first in all English. It proved to be a hit thanks to songs like “Livin’ La Vida Loca” and “Shake Your Bon-Bon.”

While critics called it cheesy pop music, it put Ricky on the radar for U.S. music and is even credited with helping promote mainstream Latin music.

Foo Fighters—There Is Nothing Left To Lose

1999 albums 17
Mick Hutson/Redferns/Getty Images

The third studio album by Foo Fighters was released on November 2, 1999, and a complete change from their past music. There Is Nothing Left To Love was softer rock based on melody. To this day, frontman Dave Grohl says it’s might be his “favorite album that they’ve ever done.”

With memorable songs like “Learn To Fly,” the 1999 album won Foo Fighters their first-ever Grammy for Best Rock Album.

Dido—No Angel

1999 albums 18
Lex Van Rossen/MAI/Redferns/Getty Images

This British singer-songwriter made waves worldwide with the release of her debut album No Angel in 1999. Most notably, the album featured the track “Thank You” which Eminem fans will recognize from his track “Stan.” Another track from the album, “Here With Me,” was also featured in the classic Christmastime romantic comedy, Love Actually.

Dido’s debut album won her several international music awards and sold over 21 million copies making it one of the top-selling British albums in history.

Macy Gray—On How Life Is

1999 albums 19

At a time when bubblegum pop and boy bands were dominating the music scene, it was refreshing to see a blues-inspired album do so well on the charts. Macy Gray’s On How Life Is featured “I Try” which was one of the biggest singled of 1999.

The single ended up winning Gray the Grammy Award for Best Female Pop Vocal Performance in 2001, which was a big deal considering the competition she was up against.


1999 albums 20
Kevin Mazur/WireImage/Getty Images

Legendary Latin guitarist Carlos Santana has been around since Woodstock but revitalized his sound, image, and popularity with his 18th studio release in 1999. Supernatural saw Santana combine his smooth guitar tracks with younger popular artists.

Everyone from Rob Thomas, Lauryn Hill, Eric Clapton, and Cee-Lo Green was featured on the album. The gamble to revitalize his career worked and hit singles like “Smooth” is still sampled by musicians today.


1999 albums 21
Catherine McGann/Getty Images

Moby was one of the earliest electronic dance musicians but it wasn’t until 1999 and the release of his fifth studio album Play that his music became mainstream. In 1999, the album was a certified cultural phenomenon in clubs all around the world.

Thanks to singles like “Honey” and “Bodyrock” Play became the top-selling electronica album of all time. Artists like Daft Punk have credited their success to Moby’s ability to make dance music mainstream.

Dr. Dre—2001

1999 albums 22
Ken Hively/Los Angeles Times/Getty Images

It may not have exactly been mainstream but for hip hop fans, Dr. Dre’s second solo album was one of the most popular. 2001 saw Dr. Dre step away from producing for other rappers and return to making his own music. Still, the album featured collaborations with many of Dr. Dre’s protégés like Eminem, Snoop Dogg, and Mary J. Blige.

Singles like “Still D.R.E.” and “Forget About Dre” were so popular that they landed Dr. Dre a guest performance on Saturday Night Live.


1999 albums 23

In a year of teeny boppers and straight-laced singers, Slipknot was definitely the black sheep. Their debut album featured singles like “Wait and Bleed” and “Spit It Out.” One music critic even compared Limp Bizkit to The Osmonds now that Slipknot was on the scene.

The nu metal music album peaked at 51 on the Billboard charts but was a huge commercial success for the band. It was certified double platinum and to date is still Slipknot’s best selling album.

David Bowie—Hours

1999 albums 24

Bowie’s 21st studio album isn’t exactly his proudest moment but it shows how artists began to change their sound and experiment around the turn of the millennium. Many people refer to Bowie’s 1999 album as “neoclassicist Bowie.”

Bowie’s previous albums had experimented heavily with electronica but Hours returned to live instruments and re-recordings of previous songs. Unfortunately, it didn’t work and Hours became Bowie’s first album since 1972 not to chart on the Billboard Top 40.

Vengaboys—The Party Album

1999 albums 25
Tim Roney/Getty Images

All you had to do was read the title of the second studio album by the Vengaboys to know what type of songs were featured. The album featured new songs as well as previously released singles. Anyone who stepped foot in a club in 1999 would recognize singles like “Boom, Boom, Boom, Boom” and “We Like To Party!”

The album made it to the top of the charts in 20 countries and notably, “We Like To Party!” was featured in a Six Flags advertisement.

Limp Bizkit—Significant Other

1999 albums 26

The rap-rock band had a lot of hype to live up to with the release of the second studio album in 1999 and in the eyes of most critics, they failed. Significant Other saw Limp Bizkit reach a new level of success commercially, but not critically. Rolling Stone and fellow musicians questioned if the band even had talent.

Still, Limp Bizkit landed a headlining gig at Woodstock 99 thanks to Significant Other. Unfortunately, their set turned to violence and numerous sexual assaults were reported.

Lolly—My First Album

1999 albums 27

You might be thinking “who on earth is Lolly?” but anyone alive in 1999 danced incessantly to her songs. My First Album by the British pop star featured singles like “Mickey” and “Viva La Radio.”

While Lolly won’t exactly go down in music history for her talent, her bubblegum pop dance hits perfectly define how strange and successful music could be in 1999. Lolly dropped off the face of the earth in 2000 only to make a sudden reappearance in 2018.


1999 albums 28
Jim Dyson/Getty Images

The debut album by the British rock band was a moderate commercial success but its singles didn’t come close to topping the charts. Even though the album wasn’t appreciated at the time since 1999 it’s become a cult classic and gained greater recognition.

A decade later, the album was ranked in the top 20 British albums of the last 20 years. Songs like “Sunburn” and “Uno” from the album are also highly requested at Muse concerts. People never appreciate true art when they see it, but hey, that’s Showbiz, baby.

Melanie C—Northern Star

1999 albums 29

Even though the Spice Girls would release one final album in 2000, 1999 marked the end of the era when both Melanie C and Geri Halliwell released their solo albums. Melanie C’s debut album, Northern Star, was released October 18, 1999, and went on to be the best selling solo album of any former Spice Girl.

The album featured singles like “Never Be The Same Again” and “I Turn To You.” Most importantly, it gave Mel C the opportunity to work with other musicians like Lisa “Left Eye” Lopes and Bryan Adams.

Geri Halliwell—Schizophonic

1999 albums 30

Halliwell was the first member of the Spice Girls to leave the group with aspirations of a solo career. It led to the highly anticipated solo album that was released June 7, 1999. Schizophonic debuted at number 4 in the UK and number 42 in the US.

Even though the album was certified double platinum and each of the four singles went to the top of the UK charts, critics panned the album. It didn’t help that Melanie C released a more successful debut album only a few months later.