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

First-round voting in the 90s Pop Song Bracket ended over the weekend weekend, and goodness gracious did madness prevail. Not one, not two, but three No. 1 seeds fell to No. 16 seeds. And now the entire bracket is chaos. Of the 32 remaining teams, 11 are double-digit seeds, and that’s including a matchup between a No. 12 and a No. 13 seed. 

One of the things I wondered when voting began was whether people would vote for songs or artists. Yes, this is a bracket of songs, but there were strong lower seeds like Notorious B.I.G., TLC and Blackstreet with some monster hits. Conversely, how would artists with multiple songs fare? No favorite took a bigger hit than the capital-D Diva herself, Mariah Carey, who saw five of her seven No. 1 hits lose in the first round. 

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. 

Second round voting will take place on Monday with the Sweet 16 and Elite 8 rounds happening on Wednesday and Friday, respectively. 

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


(16) “MmmBop” — Hanson: UMmmBC took down the No. 1 overall seed and is now ready to make a Cinderella run. 
(9) “Have You Ever Really Loved a Woman” — Bryan Adams: Have YOU ever really advanced out of the first weekend?

(12) “Creep” — TLC: The No. 12 seed has fight, but this is a difficult path to make it to the Final Four. 
(4): “That’s the Way Love Goes” — Janet Jackson: Ms. Jackson made it further than the King of Pop, so there’s that. 

(6) “Take a Bow” — Madonna: One of Madonna’s weaker No. 1 hits advanced, but it goes up against a powerhouse this round.
(3): “I Swear” — All-4-One: With only one song in the field, All-4-One has the ballad to make it to the second weekend. 

(7) “On Bended Knee” — Boyz II Men: Yes, it’s a hit, but will Boyz II Men be able to take down Sir Elton? 
(2) “Something About the Way You Look Tonight” — Elton John: We have an intriguing 2/7 matchup and this one might be a toss-up. 


(16) “Hypnotize” — Notorious B.I.G.: Had a feeling Biggie was going to spring another 1-16 upset; Ricky Martin seems like a breeze by comparison. 
(9) “Livin’ La Vida Loca” — Ricky Martin: Got a feeling Ricky’s not going to be livin’ la vida anymore.

(12) “I Don’t Want to Miss a Thing” — Aerosmith: You won’t want to close your eyes or fall asleep, since you might miss voting for this song. 
(4) “The Crossroads” — Bone Thugs-n-Harmony: Please, voters, do the right thing.

(6) “The Sign” — Ace of Base: Wow, this 3-6 matchup is between some heavyweights. Maybe the best one of the tournament.
(3) “Jump” — Kriss Kross: After jumping out of the first round, Kriss Kross has its work cut out for it here.

(10) “Vision of Love” — Mariah Carey: One of Mariah’s two songs to make it to the Round of 32. But things don’t get easier.
(2) “Smooth” — Santana feat. Rob Thomas: Does this song advance ironically or on merit? Only the voters know.


(1) “I Will Always Love You” — Whitney Houston: And IIIIIIIIIIIIIIIIIIII will always vote for YOUUUUUUUUUUUUU. 
(9) “Too Close” — Next: The voting in the last round was “too close” (52%), so can Next actually pull off the upset?

(12) “No Diggity” — Blackstreet feat. Dr. Dre: Methinks Blackstreet is another No. 12 seed that can reel off a few wins. 
(4) “
Dreamlover” — Mariah Carey: Will Mariah really get eliminated before making it out of the first weekend?

(6) “This is How We Do It” — Montell Jordan: Wow, another 3-6 matchup of absolute bangers. 
(3) “
Un-Break My Heart” — Toni Braxton: This round is all about style. Do you prefer something upbeat or heartbreaking?

(10) “Genie in a Bottle” — Christina Aguilera: An intriguing No. 10 seed, “Genie in a Bottle” actually ages pretty well. 
(2) “End of the Road” — Boyz II Men: Will this be the end of the road for Boyz II Men or Christina?


(16) “Gangsta’s Paradise” — Coolio: The third No. 16 seed to advance, “Gangsta’s Paradise” really might be Final Four material.
(8) “Baby Got Back” — Sir Mix-A-Lot: The most emphatic winner of Round 1, Sir Mix-A-Lot won’t have a cakewalk this time.

(12) “Wannabe” — Spice Girls: Are the Spice Girls legit Sweet 16 contenders, or just Wannabes? Yikes, sorry. Sorry, everyone.
(13) “No Scrubs” — TLC: The ladies from TLC might be well-represented heading into the second weekend. 

(6) “Waterfalls” — TLC: Could we have a regional final of TLC songs?
(3) “I’ll Be Missing You” — Puff Daddy: Apparently, voters were missing this song enough to advance it past the first round.

(7) “Can’t Nobody Hold Me Down” — Puff Daddy: I guess the answer is no. Nobody can’t hold Puffy down. 
(15) “I’m Too Sexy” — Right Said Fred: A fun No. 15 seed upset in Round 1, is this song literally too sexy for this bracket?

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