22 Iconic Moments That Defined ’90s Pop

We didn’t know how good we had it in the ’90s. The fashion, the TV shows the music—I know we say this about all decades past, but c’mon—I didn’t think twice about learning the Macarena! It was in my nature. In fact, I won a Nerf football in a Macarena-dancing contest at someone’s birthday party. I had no idea how cool that was until now. How is it that such iconic, irreplaceable history seemed so arbitrary? We didn’t care, we were just in it to win it—observers of the future . . . kind of how we are now.

Unfortunately, we can’t go back and relive those magical moments in real-time, but we can live vicariously through a few nostalgic gifs and photos. We’ve got it all covered—from Madonna’s iconic cone bras to Sinéad O’Connor’s controversial SNL performance, there’s no shortage of iconic ’90s music moments for us to bask in.

1. There was no better time than Hammer Time

It’s not often an artist can sample a legendary song like “Super Freak” and turn it into musical gold, But MC Hammer pulled it off with flying colors. “U Can’t Touch This” has since become a staple at all school dances and remains to be one of the most iconic songs of the ’90s. Also, parachute pants.

2. “Vogue” was more than just magazine. . .

. . . it was something to do. Personified by rigid hands and some fierce eye locks to the camera. Considering the ’90s Supermodel Era, “Vogue” couldn’t have been made at a more appropriate time. Oh, and let’s not forget Madonna’s cone bra, seen on her Blonde Ambition tour.

3. We took instructions from Vanilla Ice

We stopped, collaborated, and listened, and unabashedly indulged in the spectacle that was “Ice, Ice Baby.” Many of us still do. No judgement.

4. Lip syncing entered the collective consciousness

Milli Vanilli finagled their way into our hearts with their debut album, Girl You Know It’s True. That is, until Chuck Phillips of the Los Angeles Times blew the whistle on them. Much to our dismay, it was revealed that Rob Pilatus and Fab Morvan of Milli Vanilli were not actually the vocalists on the tracks. Duped and demystified, the public watched as Milli Vanilli had their 1990 Grammy Award for “Best New Artist” rescinded.

5. Grunge went mainstream

Thanks to Nirvana’s debut album, Nevermind, Grunge music crawled up from the underground and became widely popularized. The album’s lead single, “Smells Like Team Spirit” debuted on MTV with much success. Thank you, Nirvana, for pioneering the ’90s alternative-rock movement.

6. Big butts were on top of the charts

Sir Mix-A-Lot waged a war against flat butts with his iconic hit, “Baby Got Back.” Who knew a song about big booties could compete on the charts for #1 with Whitney Houston’s “I Will Always Love You?” Aside from its commercial success, “Baby Got Back” has gone on to achieve golden sing-along status for the world at large.

7. Dynamic duos in backwards clothes were a winning combo 

What do you get when you combine a catchy song like “Jump” with an adorable, young duo in backwards clothing? An iconic music moment, that’s what.

8. If you were too sexy, clothing was completely optional 

I’m Too Sexy” is one of the best-worst songs out there . . . or the worst-best song out there. . . I’m not really sure. It’s written from a narcissistic male-model’s perspective, which adds a refreshing, satirical element to it all. Still, I think we all knew someone who took this song to heart.

9. Sinéad O’Connor tore it up on SNL . . . literally

In an act of protest against the alleged sexual abuse of the Catholic church, Sinéad O’Connor shocked the world when she tore a picture of the Pope John Paul II to pieces during her performance on SNL. It is still one of the most controversial performances in musical history.

10. The “Parental Advisory” sticker was adopted

While we’re on the topic of controversial performances, let’s shift our focus over to the 1993 Lollapalooza Festival. The Parents Music Resource Center (PMRC) adopted the ever-so-common “Parental Advisory” sticker you see on explicit albums. Not ones for censorship, Rage Against The Machine staged a silent protest at the festival. Rather than playing their set, the guys let it all hang out with the letters P-M-R-C scrawled across their chests and duct tape sealed across their mouths.

11. Janet taught us all about love

That’s The Way Love Goes” is a timeless, sultry number that has served as a source of inspiration to musical artists across the board. Everyone from Destiny’s Child and Alicia Keys to Nelly Furtado and Britney Spears have cited the song as an influence. Personally, it reminds me of being picked up from pre-school on Fridays. 

12. Ginuwine redefined “baby-making” music 

Sure, ’90s R&B was plenty smooth before Ginuwine (we’re looking at you, Boys II Men), but “Pony” cranked up the freak-o-meter to another level. Aside from that, “Pony” also marked the success of ’90s mega-producer, Timbaland.

13. Missy Elliot made garbage bags look cool

In one of her most iconic music videos to date, “The Rain [Supa Dupa Fly],” Missy donned a onesie reminiscent of a garbage bag. High five for that fish-eye camera lens.

14. Alines Morissette’s breakup song of the century

You Oughta Know” is seething, devastating, and strangely refreshing, all at the same time. Thank you, Alanis, for one of the best breakup songs in the history of music, let alone the ’90s.

15. TLC’s good advice (Hint: it involves not chasing waterfalls)

Aside from mistaking the lyrics for “Go, go Jason Waterfalls” (and many of us did), the ladies of TLC were ankle-deep in our hearts with this song and video.

16. The Macarena took over the world 

Somewhere between collecting Beanie Babies and reading Goosebumps books, we found time to learn The Macarena. To this day, the exact words to the Macarena are still a mystery to many of us, but I’m almost certain you can perform some half-baked dance moves on the spot.

17. The Spice Girls took over the world, too 

Enter the realm of ’90s girl power. There was more to these ladies than platform sneakers and leopard-print dresses. The Spice Girls were trail blazers in their own right. Their albums, Spice and Spiceworld, were the first band since the Beatles to have two albums on the charts at the same time. And please, let’s not forget the legendary Spiceworld movie. Aside from Limited Too silk pajamas, it was a staple at all the [good] sleepovers. P.S. Here‘s the trailer.

18. The boy-band phenomenon was inescapable

It’s very, very hard to imagine the ’90s without boy bands. Where would we be without those choreographed dance moves and crushing sentimentality? The real O.Gs (98 Degrees, ‘N Sync, and Backstreet Boys) paved the way for later boy bands to take center stage after the Millennium (you’re welcome, O-Town).

19. The creation of “MMMBop“

Somehow, three blonde brothers managed to come out of nowhere and win a moment of the ’90s with a song called “MMMBop.” It was ridiculously catchy and was perfect for sing-alongs in the car with your friends (our poor, poor parents).

20. The reign of TRL

The countdown format, the screaming fans, the special guests, the Carson Daly and the mild, but informative interruptions from MTV News (we’re lookin‘ at you, Sway)—I miss it all so much. Who else wanted to be the super fan in Times Square invited onstage with Carson Daly? I know I’m not the only one who fantasized about giving a shout out to all my friends.

21. A girl named Britney Spears showed up

Enter the revival of teen pop. Britney Spears came out with a bang and a sexy schoolgirl uniform. Her debut single, “. . .Baby One More Time” reached number one in every single country it charted. Needless to say, Britney marked the beginning of an unforgettable pop era that would carry well into the 21st Century.

22. Eiffel 65’s “Blue” was up for debate

Eiffel 65’s “Blue” sparked a debate that stretched across elementary schools around the world. Many argued that the lyrics were “if I was green I would die” (at least at my school, anyway). Either way, “Blue” was sure to stick in your head all through recess.

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