Required Listening: 20 Popular Songs Turning 20 in 2019

Not sure which are better—the songs or the music videos.

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Perhaps because everyone believed the world was going to end with Y2K, the universe decided to bless us at the end of the millennium with artists like Britney Spears, the Backstreet Boys, and Blink-182, who produced some of their best work in 1999. Twenty years later, the songs—and their accompanying videos, released during Peak Music Video Season—are still incredible, and a crazy reminder of how much the artists (and the world) have changed since. Try not to feel old while you listen to these 20 songs, ahead, that are turning 20 this year. When the nostalgia hits, download our "20 Songs Turning 20 in 2019" Spotify playlist here.

1 of 20
"Genie in a Bottle" - Christina Aguilera

Can we all just take a moment to recognize how far Xtina has come since her "Genie in a Bottle" days? (She was only 19 years old here!) This summer, the former Voice judge dropped her eighth studio album—and first in six yearsLiberation, which felt like a full-circle moment for one of the best vocalists of all time.

2 of 20
"I Want It That Way" - Backstreet Boys

How to tell if a song is 20 years or older: Everybody in the club screams *in unison*, "Ain't nothin' but a heaaaartache." Unclear why there's a Backstreet Boys private jet in the background of this music video, but it's fine!

3 of 20
"Livin' La Vida Loca" - Ricky Martin

Who knew Ricky Martin was describing my life in 2019? He's now officially a #daddy, but let's be honest...he has always been. I would also like to go back in time and speak to the dancers in this music video and tell them how much I appreciate them.

4 of 20
"All Star" - Smash Mouth

If you don't think of Shrek (which premiered 18 years ago this year!!!) when you listen to "All Star," did you even have a childhood?

5 of 20
"Scar Tissue" - Red Hot Chili Peppers

Even after listening to the song more 100 times, I—without fail—get a sudden urge to pack my bags and move to California as soon as John Frusciante starts strumming his guitar in "Scar Tissue."

6 of 20
"Mambo No. 5" - Lou Bega

"Mambo No. 5" still bops and Lou Bega is a living legend, do not @ me!

7 of 20
"Heartbreaker" - Mariah Carey & Jay-Z

Me walking into 2019 like...

8 of 20
"My Name Is" - Eminem

If this song doesn't make you feel old, this picture of Eminem's daughter, Hailie, will.

9 of 20
"Wild Wild West" - Will Smith

Behold: Will Smith in his glory days. This was the year he released his second album Willennium (what a name) and was nominated for the Grammy Award for Best Rap Solo Performance.

10 of 20
"She's So High" - Tal Bachman

The song you memorized every word to—but never knew the singer of—is officially 20. The more you know!

11 of 20
"Bills, Bills, Bills" - Destiny's Child

A 17-year-old Beyoncé in this "Bills, Bills, Bills" music video is e-v-e-r-y-t-h-i-n-g...

12 of 20
"Big Pimpin'" - Jay-Z ft. UGK

...And look! It's Jay-Z. This is nine years before he and Beyoncé got married.

13 of 20
"What's My Age Again?" - Blink-182

Yes, "What's My Age Again" is 20 years old this year. No, I am not okay, thanks for asking! @MarkHoppus, @TravisBarker, @MattSkiba when is the 20-year Enema of the State anniversary tour?

14 of 20
"All the Small Things" - Blink-182

Speaking of, Enema of the State is the best album of all time. Naturally, we couldn't not include "All the Small Things" on this list, too. Miss you, Tom DeLonge.

15 of 20
"(You Drive Me) Crazy" - Britney Spears

Three icons, one music video. Please enjoy Britney Spears, Melissa Joan Hart, and Adrian Grenier in Spears' "(You Drive Me) Crazy" from her very first album, ...Baby One More Time. Never forget putting the CD into the boombox and pushing play on this one.

16 of 20
"My Own Worst Enemy" - Lit

Rock band Lit was really on to something when they named their band in 1988. Their hit "My Own Worst Enemy" is the song you're shocked the frat guy across the bar knows all the words to, which is ironic considering he's actually your own worst enemy.

17 of 20
"We Like to Party!" - Vengaboys

Eurodance group Vengaboys made the ultimate sleepaway camp jam (no parents!) with "We Like to Party!" Petition to add it to every club's playlist for summer 2019.

18 of 20
"Waiting For Tonight" - Jennifer Lopez

Jennifer. Lopez. Many (okay, me, and probably a lot of other music critics) consider "Waiting For Tonight" the best song of J.Lo's career. It won the MTV Video Music Award for Best Dance Video in 2000. She looks exactly the same.

19 of 20
"Learn to Fly" - Foo Fighters

It doesn't matter what you think of the Foo Fighters, their "Learn to Fly" is 20 years old and we're celebrating it.

20 of 20
"I Try" - Macy Gray

There are some artists you know, and other artists you know. The inimitable Macy Gray's breathrough hit "I Try" that would play in every 2000s rom-com has already been around for 20 years.

Fun fact: Gray worked with Dolly Parton on a re-recording of "Two Doors Down" for the new-ish Netflix movie Dumplin'. More Gray in 2019, please.


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