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

March Madness was over before it really began due to the coronavirus pandemic, but that doesn’t mean we have to cancel brackets altogether, does it? Now more than ever, we need something — anything — to keep us going while sports are on hiatus. And what better way to do that while engaging in some social distancing than to relive simpler times?

What about a time when colors were just a little more neon, hair was a little bigger and flannel wasn’t for hipsters. We’re taking a look back at the 1990s and the top hits of that era: a winner-take-all battle of musical heavyweights — in bracket form.

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. As such, there’s no “Ice, Ice, Baby” by Vanilla Ice or “All My Life” by K-Ci and Jojo. There’s no Hootie and the Blowfish. 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. 

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

The Radio and MP3 Regions will be open on Wednesday with the Cassette and CD regions open on Thursday. The second round will commence on Monday, and so on. Without further delay, here are the seeds for the top hits from the 90s.


(1) “One Sweet Day” — Mariah Carey / Boyz II Men: Two 90s powerhouses joined forces for the top overall seed.
(16) “MmmBop” — Hanson: Do we have a UMBC situation on our hands here?

(8) “Rush Rush” — Paula Abdul: Can Paula Abdul’s second song in this region beat Bryan Adams’ second song?
(9) “Have You Ever Really Loved a Woman” — Bryan Adams: Somebody technically has to win this matchup, right?

(5) “(Everything I Do) I Do It For You“– Bryan Adams: Two words: F-R-E-A-K-I-N’  B-A-L-L-A-D.
(12) “Creep” — TLC: Before “Waterfalls” and “No Scrubs,” “Creep” was a bona fide jam.

(4): “That’s the Way Love Goes” — Janet Jackson: The King of Pop wasn’t the only Jackson to own the 90s. 
(13): “Angel of Mine” — Monica: When those chimes hit, I don’t know if there was a more quintessential 90s song than this.

(6) “Take a Bow” — Madonna: The Material Girl may have collaborated with Babyface, but will that hold off a 6/11 upset?
(11) “Because I Love you (The Postman Song)” — Stevie B: A monster hit at the beginning of the 90s, but does it have the staying power?

(3): “I Swear” — All-4-One: Oh man, high school slow dances were never the same after this. Total game-changer. 
(14): “Opposites Attract” — Paula Abdul / The Wild Pair: The music video is the strength of this bubbly hit.

(7) “On Bended Knee” — Boyz II Men: Goodness, gracious, the music video is a GLOW UP. 
(10) “If You Had My Love” — Jennifer Lopez: J.Lo’s first single from her first album launched her into worldwide stardom.

(2) “Something About the Way You Look Tonight” — Elton John: Strong mom and dad date night energy here.
(15) “Love Takes Time” — Mariah Carey: Mariah had so many No. 1 hits she’s both a favorite and an underdog.


(1) “Macarena” — Los Del Rio: You know what time it is. Wedding dance floors were never the same.
(16) “Hypnotize” — Notorious B.I.G.: Biggie’s hits still slap, but can this one overtake the No. 1 seed?

(8) “I’d Do Anything for Love (But I Won’t Do That)” — Meat Loaf: This 90s’ rock opera by Mr. Loaf was perfect for commercialism
(9) “Livin’ La Vida Loca” — Ricky Martin: She’s into superstition, black cats and 8/9 matchups.

(5) “Can’t Help Falling in Love With You” — UB40: Maybe this will be a 5/12 so let’s see what the match up is — oh, oh no.
(12) “I Don’t Want to Miss a Thing” — Aerosmith: This was Aerosmith’s only No. 1 Hot 100 hit and that feels like a crime.

(4) “The Crossroads” — Bone Thugs-n-Harmony: No lie, it took a minute to remember this song now but it almost ages better
(13) “How Am I Supposed to Live Without You?” — Michael Bolton: What was Michael Bolton’s bigger accomplishment, a No. 1 hit, or starring in “Office Space?”

(6) “The Sign” — Ace of Base: The 90s had a lot of slow, R&B style hits, so “The Sign” was a nice change of pace.
(11) “Bump N’ Grind” — R. Kelly: Well, it’s not “I Believe I Can Fly” that’s for sure.

(3) “Jump” — Kriss Kross: Who knew a couple of kids could wear their clothes backwards and launch straight to stardom?
(14) “Step by Step” — New Kids on the Block: This is NKOTB’s biggest hit, but even after 30 years, it’s still pretty corny.

(7) “I’m Your Angel” — R. Kelly and Celine Dion: Honestly, you could not have picked a duet with two more different people.
(10) “Vision of Love” — Mariah Carey: Obviously Mariah Carey had pipes, but she unleashes them in this song.

(2) “Smooth” — Santana featuring Rob Thomas: Man, it’s a hot one!
(15) “To Be With You” — Mr. Big: A rare rock band in the tournament, Mr. Big faces a steep challenge.

Voting on the following regions begins Thursday


(1) “I Will Always Love You” — Whitney Houston: Often imitated, never duplicated, this is an all-timer for karaoke.
(16) “Stay (I Missed You)” — Lisa Loeb: Oh, yeah, now we’re getting into indie/alternative 90s. 

(8) “Save the Best for Last” — Vanessa Williams: This soft adult ballad was a favorite of elevators everywhere.
(9) “Too Close” — Next: Will this round be too close to call? Will this song make it to the next round? Sorry, everyone, that was bad.

(5) “Black or White” — Michael Jackson: We’ve had a couple of Janet Jackson songs, but Mike finally gets in the field. 
(12) “No Diggity” — Blackstreet: Dr. Dre collaborated on this No. 1 hit and we’ve got a possible 5/12 upset. 

(4) “Dreamlover” — Mariah Carey: Mariah has a ton of hits in this field, so I feel like an upset is coming at some point. 
(13) “Believe” — Cher: Oh, hell yeah. Cher went full autotune in this house favorite. 

(6) “This is How We Do It” — Montell Jordan: Man, Nickelodeon and Disney T.V. movies loved this song. 
(11) “Hero” — Mariah Carey: Like a lot of No. 11 seeds, “Hero” comes from a powerhouse, but sort of limps to the finish line.

(3) “Un-Break My Heart” — Toni Braxton: Damn, Toni, I don’t know who hurt you, but I am so, so sorry. 
(14) “Escapade” — Janet Jackson: Janet’s second No. 1 single in the field is a big underdog. 

(7) “Because You Loved Me” — Celine Dion: Big 90s mom energy from Celine Dion here. 
(10) “Genie in a Bottle” — Christina Aguilera: The pop princess wars with Britney Spears started when this banger hit. 

(2) “End of the Road” — Boyz II Men: Credit where it’s due, Boyz II Men had the formula down for a 90s No. 1 hit. 
(15) “Emotions” — Mariah Carey: It’s one of her more upbeat singles, if that’s your jam. 


(1) “I’ll Make Love to You” — Boyz II Men: A little awkward, yes, but you can’t argue with the popularity.
(16) “Gangsta’s Paradise” — Coolio: A little stunning that it made it in as a No. 16 seed, but where’s the love for “Amish Paradise?”

(8) “Baby Got Back” — Sir Mix-A-Lot: More than 20 years later, and I still have no idea what this song is about. 
(9) “The First Night” — Monica: This seems like a mismatch at 8/9, but we’ll see if Monica has what it takes. 

(5) “Informer” — Snow: Have to say, I’m still a little stunned this was a hit, let alone a No. 1 hit. 
(12) “Wannabe” — Spice Girls: Somehow criminally under-seeded in this field, I smell a 5/12 upset.

(4) “Fantasy” — Mariah Carey: This wasn’t Mariah’s biggest hit, but it’s probably my personal favorite.
(13) “No Scrubs” — TLC: The R&B trio burst back on to the scene in the late 90s with this massive hit taking shots at low life bros everywhere. 

(6) “Waterfalls” — TLC: This was their biggest single ever, but it is their best?
(11) “The Power of Love” — Celine Dion: No, it’s not Huey Lewis and the News. Would that have been better? Maybe. 

(3) “I’ll Be Missing You” — Puff Daddy: Diddy’s homage to the Notorious B.I.G. with a little help from a Police sample, Faith Evans and 112 made its way to No. 1. 
(14) “Vogue” — Madonna: For an artist who managed to reinvent herself every decade, “Vogue” was peak 90s Madonna. 

(7) “Can’t Nobody Hold Me Down” — Puff Daddy: Can’t nobody break my stride, either. Mase is featured, of course.
(10) “Nothing Compares 2 U” — Sinead O’Connor: Another under-seeded song. Does it have the power to make a run?

(2) “The Boy is Mine” — Brandy / Monica: The 90s had a lot of great collaborations for No. 1 hits, this might be the best. 
(15) “I’m Too Sexy” — Right Said Fred: The No. 1 hit among those who are not, in fact, too sexy. 

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