90s Pop Songs Bracket — Sweet 16: Which was the greatest No. 1 hit from back in the day?

Traditionally speaking, the first weekend of the NCAA Tournament is for the madness: buzzer beaters, surprising early exits, things you didn’t expect to happen. By the Sweet 16 and Elite Elite during the second week, at least some semblance of normalcy reigns with only a couple of outliers. 

That may work for basketball, but it most certainly does not work for music. After one “weekend,” the Sweet 16 of the 90s Pop Music Bracket is in total disarray. (Frankly, we couldn’t be more proud of you, the voters.) Three of the No. 16 seeds that advanced past the first round — “MmmBop,” “Hypnotize” and “Gangsta’s Paradise” — have gone even further. In all, 11 of the 16 remaining teams are No. 6 seeds or lower. In fact, the Cassette Region is made up of three seeds of 13 or lower. Powerhouse Mariah Carey? All seven songs eliminated. Meanwhile, TLC still has all three of its songs in the field. 

However, among the handful of higher seeds that remain, there are some bona fide bangers. “I Will Always Love You,” “Smooth,” “The Crossroads,” “I Swear” and “Jump” are still around and will face their toughest competition yet. Say this for the bracket: all the fat has been cut. The remaining songs are jams. The voting just became that much harder. 

The 64-song field is filled with No. 1 hits seeded based on weeks at No. 1 on the Billboard Hot 100 chart from 1990-99. No. 1 seeds stayed atop the Hot 100 the longest, while No. 16 seeds were No. 1 for the shortest amount of time. (In other words, don’t get mad at us for the seedings.)

Remember: These are the top 64 pop songs of the ’90s, so there’s a cutoff. There’s no Hootie and the Blowfish, for example. Still, anyone who was alive and well in the ’90s should know most, if not all, of these songs. They’re bangers. After all, they were No. 1 hits. For anyone who is uninitiated, all songs have links. 

Sweet 16 voting takes place today with Elite Elite voting going down on Friday. Final Four and championship voting will take place next week. 

Voting for the Sweet 16 round and every round will take place on our Cover 3 Podcast Twitter account and in the embedded tweets below.


(16) “MmmBop” — Hanson:  UMmmBC had an easier road than expected to the Sweet 16, but Hanson runs into perhaps TLC’s best hit ever. 
(12) “Creep” — TLC: Either way, a double-digit seed is making it to the MP3 Radio Region final.

(3): “I Swear” — All-4-One: The battle of power ballads between vocal groups with numbers in their name commences. 
(7) “On Bended Knee” — Boyz II Men: This ’90s powerhouse has one song left in the field — can it advance?


(16) “Hypnotize” — Notorious B.I.G.:  Like Hanson, Biggie had a somewhat easy run to the Sweet 16, but the intensity picks up here. 
(4) “The Crossroads” — Bone Thugs-n-Harmony: I always figured “The Crossroads” would get this far, but the path to the Final Four intensifies greatly starting now.

(3) “Jump” — Kriss Kross: The boys with the backwards clothes have advanced comfortably so far, but this is a ’90s heavyweight fight. 
(2) “Smooth” — Santana feat. Rob Thomas: I’ve wondered if “Smooth” has made it this far ironically. Guess we’ll find out.


(1) “I Will Always Love You” — Whitney Houston: The lone No. 1 seed remaining goes against a feisty No. 12 seed. No guarantees here for Whitney. 
(12) “No Diggity” — Blackstreet feat. Dr. Dre: Another lower seed to advance comfortably, but Whitney Houston is the G.O.A.T.

(6) “This is How We Do It” — Montell Jordan: Low-key, I can see “This is How We Do It” making a Final Four run. 
(10) “
Genie in a Bottle” — Christina Aguilera: Maybe voters will prove me wrong, but this feels like an underrated battle.


(16) “Gangsta’s Paradise” — Coolio: The third No. 16 seed goes against the second of three TLC songs. 
(13) “No Scrubs” — TLC: Will we get a Cassette Region final of all TLC?

(6) “Waterfalls” — TLC: TLC’s biggest hit faces an interesting No. 15 seed, and I’m not sure how voters are going to go here.
(15) “I’m Too Sexy” — Right Said Fred: Like “Smooth,” I wonder how far this will advance on merit. “Waterfalls” is an all-timer. 

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