20 Songs That Turn 20 This Year

by Sa'iyda Shabazz

Music has a way of transporting us back to another time in our lives. When life was simpler, or happier, or whatever. How often does it happen that you hear a song and you’re instantly back in that moment, maybe standing on your front porch having your first kiss, or in your bed crying over your first breakup, or seeing your favorite artist on TV for the first time?

For many of us, the music of the ’90s is the background to our earliest memories. The ’90s were the soundtrack to our adolescence, and these songs will always hold a lot of significance for us.

It’s hard to believe that 1998 was 20 (!!) years ago. It honestly feels like it was just yesterday, but now those songs we pumped in our parents’ cars or in our bedrooms are being played on the oldies stations. Nothing makes you feel older than hearing Third Eye Blind on the classic rock station.

When we tell younger folks about the mixtapes we made in the ’90s, they’re confused for an assortment of reasons. These are some of the ’90s songs we’d rush to tape on the radio, hoping the DJ wouldn’t talk over the end, thereby ruining our perfect recording. And even though our favorite songs that were released in ’98 (though they may be on albums released in ’97) may be almost old enough to drink, they’ll be forever young in our eyes.

1. “Baby One More Time” — Britney Spears

With three simple words, an icon was born. Britney Spears became the poster girl for the late ’90s pop music explosion. That school girl outfit has been permanently burned into our memories.

2. “Tearin’ Up My Heart” — *NSYNC

Technically, “Tearin’ Up My Heart” was *NSYNC’s second single, but it was the first one to make a real impact. It was a mainstay on the Total Request (and later TRL) “top three” for months. And who could forget Justin Timberlake in a tank top on a bed?

3. “When The Lights Go Out” — Five

British boy band Five didn’t make the same impact as some of their American peers, but this song certified them as the “bad boys.” They were singing about sexual things, and that was hugely exciting for tween girls.

4. “I’ll Be” — Edwin McCain

This song will forever be associated with the moment Dawson and Joey kissed on Dawson’s Creek. For others, it will be associated with being played at a lot of weddings.

5. “Gettin’ Jiggy Wit It” — Will Smith

Will Smith was always the “clean” rapper, and not only does this song hold up, it introduced us to the word “jiggy.”

6. “Angel” — Sarah McLachlan

Admit it, you can’t hear this song and not think of puppies in cages. What was once just a very beautiful, if not melancholy song, is now forever associated with late night ASPCA commercials.

7. “The Boy Is Mine” — Brandy and Monica

In the history of teen pop, there has never been a more iconic duet. Brandy and Monica were queens, and seeing them fight over Mekhi Phifer was just gold.

8. “All My Life” — K-Ci & Jojo

You couldn’t go to a wedding without hearing this song by the two former lead singers of Jodeci. Though I still don’t understand the lyrics, “Close to me you’re like my mother / close to me you’re like my father / close to me you’re like my sister / close to me you’re like my brother.” Whatever, we’re willing to overlook the mild confusion for this one.

9. “When You Believe” — Whitney Houston and Mariah Carey

This song from the soundtrack of The Prince of Egypt was the biggest battle of the divas of all time. By 1998, both women were icons, and watching them perform this still gives me chills.

10. “One Week” — Barenaked Ladies

There have never been more tongue twisting lyrics in a song on the radio. You know you tried desperately to learn the words past “Chickity China, the Chinese chicken…”

11. “This Kiss” — Faith Hill

One of the first country pop crossovers, it was included in the classic film Practical Magic, which also turned 20 this year.

12. “You’re Still the One” — Shania Twain

Another popular country crossover — not only did it cement Shania Twain as a sex symbol, but also as a diva.

13. “The Dope Show” — Marilyn Manson

Just about every parent was worried about catching their kid watching the video for “The Dope Show.” But really, it’s just an awesome song/video.

14. “Sex & Candy” — Marcy Playground

Having “sex” right there in the title really laid it all out there. My mom tried to forbid me from listening to it, but I reminded her that she couldn’t control the radio.

15. “Pretty Fly For A White Guy” — The Offspring

Proving that white males have always been the butt of the joke (and often for good reason), The Offspring’s song about a total poser was so much fun to sing along to.

16. “Too Close” — Next

The school dance really got started when “Too Close’” came on. It was the soundtrack to a lot of very close dancing, though its lyrics might be a little problematic nowadays.

17. “I Don’t Want to Miss A Thing” — Aerosmith

Aerosmith’s ’90s renaissance really culminated with “I Don’t Want to Miss a Thing,” which was on the soundtrack to Armageddon and made our hearts break all over again.

18. “Doo Wop (That Thing)” — Lauryn Hill

After The Fugees but before she became Ms. Lauryn Hill, there was just Lauryn Hill, the amazing singer who hit it out of the park with her first solo single.

19. “My Heart Will Go On” — Celine Dion

If you weren’t sick of your mom warbling along to this song while she did the dishes, you were likely fighting with your friends about which one of you was going to marry Leo DiCaprio.

20. “Are You That Somebody” — Aaliyah

RIP baby girl. Aaliyah was the princess of R&B, and this song, another TRL staple, just proved why. But the crying baby sound is still weird.

This is by no means a comprehensive list because 365 days is long, but there is no way you can hear one of these 20 songs and not be transported back to the simpler times of the ’90s.