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Welcome to ’99 Music Week

The year’s hottest hits turn 20. Here’s a deeper look into your favorite songs and albums of 1999.

Contributors: Ringer Staff

Remember a simpler time when we were all just “Livin’ la Vida Loca”? Or when Sisqó’s “Thong Song” couldn’t get out of your head? Or when you had to keep asking, “What’s My Age Again?” The Ringer’s 40 best songs and albums from 1999 will transport you to a golden age of catchy hits and bad fashion.

Explore features throughout the week that take a magnifying glass to the year’s classics and the state of music as a whole. What were the most controversial songs of the year? What was going on with rap in ’99? Check out The Ringer’s coverage on 1999 Music Week below:

26 Total Updates Since
Jul 1, 2019, 12:27pm EDT

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August 27, 2019
Does Woodstock ’99 Say Anything About Its Generation, or Was It Just Pure Chaos?

By Steven Hyden

The final episode of ‘Break Stuff’ explores the aftermath of the ill-fated event and how it compares to another recent disastrous festival you may have heard of
August 20, 2019
The Moment That Woodstock ’99 Went Up in Flames

By Steven Hyden

Episode 7 of ‘Break Stuff’ looks at the Sunday riots and violence that you remember Woodstock ’99 for
August 13, 2019
The Legacy of Woodstock ’99 Is Sexual Assault

By Steven Hyden

Episode 6 of ‘Break Stuff’ explores the violence against women that garnered headlines in the wake of the festival
August 6, 2019
The Human Toll of Woodstock ’99

By Steven Hyden

Episode 5 of ‘Break Stuff’ looks at one family shattered as a result of the ill-fated festival
August 2, 2019
A 1999 Album Tour at Amoeba Music Hollywood

By The Ringer Staff

Chris Ryan and Micah Peters hit up Amoeba Music in Hollywood to find some of their favorite albums from the year from artists like Jay-Z, Blink-182, and more
August 2, 2019
The Best Album of 1999 Was … Y2K Paranoia

By Lindsay Zoladz

"Will 2K." ‘Millennium.’ ‘FanMail.’ In a moment suffused with nervous excitement and vaguely apocalyptic grandiosity, pop music was on the brink of something, even if no one knew exactly what.
August 2, 2019
The Band That Defined—and Shed—the “Next Radiohead” Label

By Ian Cohen

Once pegged as the successor to both Thom Yorke and Co. and Oasis, Travis’s megasuccessful 1999 placed the group in the rarefied air of Britpop royalty
August 2, 2019
The Backstreet Boys Were Better Than ’NSync (and Every Other Artist in 1999)

By Shea Serrano

Presenting an undeniable case for the importance of ‘Millennium’ and the Backstreetiness of AJ; also, how BSB would win a head-to-head matchup against their main boy-band rivals
August 1, 2019
The Story Behind the Two Most Controversial Rap Songs of 1999

By Thomas Golianopoulos

A young 50 Cent needed a hit—so he wrote a song about mugging famous rappers. Meanwhile, the group Screwball recorded a track about killing Rudy Giuliani. Here’s how two controversial rap upstarts were thwarted in an era that wasn’t ready for the drama.
August 1, 2019
Look at These Faces: How Handsome Boy Modeling School Created the Perfect Album for ’99

By Rob Harvilla

Producers Prince Paul and Dan the Automator invited all of their good-looking friends to a party 20 years ago, and the result was a weird, hilarious rap record that stands the test of time
August 1, 2019
How Jay-Z’s ‘Vol. 3’ Explained Rap Music in 1999—and Predicted Its Future

By Donnie Kwak

With disparate styles and references to where hip-hop was headed, Jigga’s colossal fourth album is the perfect time capsule for the genre on the eve of the millennium
July 31, 2019
Don’t Grow Up, Blow Up: The Rise of Blink-182

By Alan Siegel

In 1999, with a dedication to stunted immaturity (and streaking), an unlikely Southern California rock trio became big enough to rival the likes of ‘NSync and the Backstreet Boys
July 31, 2019
‘Tha Block Is Hot’ Is Lil Wayne’s Superhero Origin Story

By Micah Peters

A then-17-year-old Weezy was eons away from his finished form in 1999, but his debut solo album is a crucial moment in his—and Cash Money’s—development
July 30, 2019
Believe in Her or Not, Cher Has Always Believed in Herself

By Lindsay Zoladz

Decades before the likes of Kim Kardashian, the iconic singer-actress born Cherilyn Sarkisian invented "famous just because." But in 1999, she took her career to heights that were virtually beyond belief. And she hasn’t budged since.
July 30, 2019
What Is the Best Song From 1999?

By The Ringer Staff

Does it belong to the Backstreet Boys? Britney Spears? Mariah Carey? Ringer staffers debate the best songs from one of the most varied years in music.
July 30, 2019
How the Early Parts of Woodstock ’99 Set the Stage for Disaster

By Steven Hyden

The first night of the festival was a relative calm before the chaos that the festival is best remembered for—but still contained some signs of trouble to come
July 30, 2019
Taking You Back to the 1999 MTV Video Music Awards

By Andrew Gruttadaro, Kate Knibbs, and Rob Harvilla

We talk about Chris Rock’s opening monologue, Diana Ross’s jiggling Lil’ Kim’s boob, Paul McCartney’s mispronouncing Lauryn Hill’s name, and other iconic moments from the show
July 30, 2019
“No Scrubs” vs. “No Pigeons”: The Battle of the Sexes That Shook Radio in 1999

By Julian Kimble

After R&B supergroup TLC dropped "No Scrubs," a little-known New York rap group called Sporty Thievz responded with "No Pigeons." It launched a gender war on and off the airwaves, amplified by two trios, two songs, one beat, and zero apologies.
July 30, 2019
Why Wilco’s ‘Summerteeth’ Is the Best Album of 1999

By Elizabeth Nelson

A celebration of Wilco’s masterful reboot of classic rock and new wave
July 29, 2019
How LFO’s “Summer Girls” Explains the Weird, Wonderful Music of 1999

By Rob Harvilla

Remembered today primarily as an ode to girls in Abercrombie & Fitch, the song and the tragic story behind it paint a picture of the music at the turn of the century
July 29, 2019
Rage Against the Machine’s ‘The Battle of Los Angeles’ Is 20, and It Hasn’t Aged a Day

By Sean Fennessey

Rage was loud, angry, and activist. They saw the future and screamed about it. Until they didn’t anymore.
July 23, 2019
Before Woodstock ’99 Was a Nightmare, It Was One Town’s Dream

By Steven Hyden

Episode 3 of ‘Break Stuff’ investigates how the festival landed in Rome, New York, and some of the early warning signs that something was awry
July 16, 2019
Everything You Know About the First Woodstock Is Wrong

By Steven Hyden

Episode 2 of ‘Break Stuff’ explores the 1969 festival, which wasn’t everything the famous documentary would have you believe
July 9, 2019
‘Break Stuff’: Just One of Those Days

By Steven Hyden

It’s the one thing people think they know about Woodstock ’99—Fred Durst of Limp Bizkit encouraged shirtless hooligans to "break stuff"
July 9, 2019
Limp Bizkit Got the Blame for the Woodstock ’99 Riots. But It’s Not That Simple.

By Steven Hyden

The first episode of ‘Break Stuff,’ The Ringer’s new documentary podcast series about the doomed festival, explores whether the bad boys of nu metal were really the cause of the chaos

Welcome to ’99 Music Week

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