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I was curious as to what the best song of the 90s and 00s would be. To figure this out, I created a massive 256-song tournament, and ran through it with my partner antarris
Our Filled Bracket http://www.d8uv.org/misc/song-tournament-1992-2007-filled-out.png
What the hell is that thing up there
For each year in our tournament, I took the top 16 songs from Billboard’s Year-End Hot 100 chart (which measures a song’s overall popularity over the course of the year), and seeded them appropriately (so that the more popular songs have a slight advantage). Then, I took the output of the 16 years, and ran a tournament to find the best song of the 90s, the best song of the 00s, then pitted those two winners in the grand final.
Note: In the filled-out bracket, we were mostly in agreement. When we absolutely couldn’t agree, we had to split. Splits are denoted by slashes; the song on top is d8uv
’s choice, and the song on bottom is antarris
Notes from the tournament
1992—Winner: “Under The Bridge”
- End of the Road - Boyz II Men vs. I'll Be There - Mariah Carey
- Under the Bridge - Red Hot Chili Peppers vs. All 4 Love - Color Me Badd
- Baby-Baby-Baby - TLC vs. To Be with You - Mr. Big
- Save the Best for Last - Vanessa Williams vs. I'm Too Sexy - Right Said Fred
- Tears in Heaven - Eric Clapton vs. I Love Your Smile - Shanice
- Jump - Kris Kross vs. Black or White - Michael Jackson
- My Lovin' (You're Never Gonna Get It) - En Vogue vs. Just Another Day - Jon Secada
- Baby Got Back - Sir Mix-a-Lot vs. Achy Breaky Heart - Billy Ray Cyrus
: Note: “Smells Like Teen Spirit”–you know, the song that changed the entire rock genre—only got up to 32. And yet, “Just Another Day”, a song that you have never heard of, was the 10th most popular song. What the hell was wrong with the people of 1992? antarris
: Not everyone was an angsty white suburban teenager, you know.
1993—Winner: “Nuthin’ But A ‘G’ Thang”
- I Will Always Love You - Whitney Houston vs. Dazzey Duks - Duice
- Dreamlover - Mariah Carey vs. Rump Shaker - Wreckx-n-Effect
- Freak Me - Silk vs. In the Still of the Nite - Boyz II Men
- That's the Way Love Goes - Janet Jackson vs. Don't Walk Away - Jade
- Weak - SWV vs. Nuthin' but a 'G' Thang - Dr. Dre
- Can't Help Falling in Love - UB40 vs. Knockin' da Boots - H-Town
- If I Ever Fall in Love - Shai vs. Informer - Snow
- Whoomp! (There It Is) - Tag Team vs. Lately - Jodeci
: I don’t even know who like a third of these people even are. “I Will Always Love You” nearly won my bracket.
1994—Winner: d8uv: “Whatta Man”, antarris: “Don’t Turn Around”
- The Sign - Ace of Base vs. Without You / Never Forget You - Mariah Carey
- All for Love - Bryan Adams, Rod Stewart and Sting vs. All That She Wants - Ace of Base
- Hero - Mariah Carey vs. Again - Janet Jackson
- The Power of Love - Céline Dion vs. I'll Remember - Madonna
- Stay (I Missed You) - Lisa Loeb and Nine Stories vs. Bump n' Grind - R. Kelly
- I'll Make Love to You - Boyz II Men vs. Whatta Man - Salt-n-Pepa and En Vogue
- Breathe Again - Toni Braxton vs. Don't Turn Around - Ace of Base
- I Swear - All-4-One vs. Wild Night - John Mellencamp feat. Meshell Ndegeocello
: The Sign was the first album I ever owned. I sang “Don’t Turn Around” in the shower through my mid-twenties. Sorry-not-sorry. d8uv
: This was the year of Ace of Base, and as much as I love my trashy eurodance, the sound hasn’t aged particularly well. antarris
: I live for my trashy eurodance. Fight me.
1995—Winner: d8uv: “Waterfalls”, antarris: “Gangsta’s Paradise”
- Gangsta's Paradise - Coolio feat. L.V. vs. Have You Ever Really Loved a Woman? - Bryan Adams
- Take a Bow - Madonna vs. Don't Take It Personal (Just One of Dem Days) - Monica
- On Bended Knee - Boyz II Men vs. Water Runs Dry - Boyz II Men
- Kiss from a Rose - Seal vs. Freak Like Me - Adina Howard
- Another Night - Real McCoy vs. I Know - Dionne Farris
- Creep - TLC vs. Run-Around - Blues Traveler
- Fantasy - Mariah Carey vs. This Is How We Do It - Montell Jordan
- Waterfalls - TLC vs. I Can Love You Like That - All-4-One
: “Waterfalls” is just a touch behind for me, probably because my little sister played it incessantly. She was seven. d8uv
: Antarris called “Gangsta’s Paradise” out as “the only rap song every white person knows”. This was meant as a compliment, but I know better.
1996—Winner: d8uv: “Tha Crossroads”, antarris: “C’mon N’ Ride It (The Train)”
- Macarena (Bayside Boys Mix) - Los del Río vs. Sittin' Up in My Room - Brandy
- I Love You Always Forever - Donna Lewis vs. You're Makin' Me High / Let It Flow - Toni Braxton
- Always Be My Baby - Mariah Carey vs. Missing - Everything but the Girl
- Nobody Knows - The Tony Rich Project vs. Ironic - Alanis Morissette
- Give Me One Reason - Tracy Chapman vs. C'mon N' Ride It (The Train) - Quad City DJ's
- Because You Loved Me - Celine Dion vs. Exhale (Shoop Shoop) - Whitney Houston
- Tha Crossroads - Bone Thugs-n-Harmony vs. Twisted - Keith Sweat
- One Sweet Day - Mariah Carey and Boyz II Men vs. Follow You Down / Til I Hear It from You - Gin Blossoms
: When pressed for comment, all antarris
said was “... it’s a choo-choo train.” antarris
: Pure fucking lyrical genius. “Tha Crossroads” is my second favorite, though. d8uv
: Still, I found myself honestly surprised at how much I liked “Tha Crossroads”.
- Something About the Way You Look Tonight / Candle in the Wind 1997 - Elton John vs. Nobody - Keith Sweat feat. Athena Cage
- Return of the Mack - Mark Morrison vs. How Do I Live - LeAnn Rimes
- Can't Nobody Hold Me Down - Puff Daddy feat. Mase vs. MMMBop - Hanson
- Un-Break My Heart - Toni Braxton vs. For You I Will - Monica
- I Believe I Can Fly - R. Kelly vs. Quit Playing Games (With My Heart) - Backstreet Boys
- I'll Be Missing You - Puff Daddy feat. Faith Evans and 112 vs. You Make Me Wanna... - Usher
- Don't Let Go (Love) - En Vogue vs. Wannabe - Spice Girls
- Foolish Games / You Were Meant for Me - Jewel vs. Bitch - Meredith Brooks
: This—like 1994—was a surprisingly weak year. Every matchup other than the final was super easy, and even the final wasn’t that hard. antarris
: “Semi-Charmed Life” was #17. It would have won my bracket. I probably should’ve bought it instead of recording the video off MTV.
1998—Winner: “How’s It Going To Be”
- Too Close - Next vs. My Way - Usher
- Candle in the Wind 1997 - Elton John vs. Nice & Slow - Usher
- How Do I Live - LeAnn Rimes vs. No, No, No - Destiny's Child
- Truly Madly Deeply - Savage Garden vs. My Heart Will Go On - Celine Dion
- Together Again - Janet vs. How's It Going to Be - Third Eye Blind
- You're Still the One - Shania Twain vs. Gettin' Jiggy wit It - Will Smith
- All My Life - K-Ci & JoJo vs. I Don't Want to Wait - Paula Cole
- The Boy Is Mine - Brandy and Monica vs. You Make Me Wanna... - Usher
: This year was also surprisingly weak. Lots of “this is my third favorite song from this artist.” d8uv
: Elton John cheated with a mediocre song that made into two years of this tournament.
1999—Winner: “Livin’ la Vida Loca”
- Believe - Cher vs. I'm Your Angel - R. Kelly and Celine Dion
- Every Morning - Sugar Ray vs. Nobody's Supposed to Be Here - Deborah Cox
- ...Baby One More Time - Britney Spears vs. If You Had My Love - Jennifer Lopez
- Heartbreak Hotel - Whitney Houston feat. Faith Evans and Kelly Price vs. Slide - Goo Goo Dolls
- Kiss Me - Sixpence None the Richer vs. Where My Girls At? - 702
- Angel of Mine - Monica vs. Have You Ever? - Brandy
- Genie in a Bottle - Christina Aguilera vs. Livin' la Vida Loca - Ricky Martin
- No Scrubs - TLC vs. I Want It That Way - Backstreet Boys
: This had the hardest matchup in the entire tournament. The seeding was unkind, and forced two songs that would have won the year if they didn’t have to clash. “No Scrubs” vs. “Livin’ la Vida Loca”. But, in the end, Ricky Martin just barely beat TLC. I’m still not sure if this was the right choice. antarris
: If “No Scrubs” had won, it would have made it just as far as “Livin’ La Vida Loca” did. It’s that good. My mom thinks we made the wrong choice, though.
- Breathe - Faith Hill vs. There You Go - Pink
- Amazed - Lonestar vs. Bent - Matchbox Twenty
- Everything You Want - Vertical Horizon vs. Try Again - Aaliyah
- I Wanna Know - Joe vs. Jumpin', Jumpin' - Destiny's Child
- Say My Name - Destiny's Child vs. Higher - Creed
- Maria Maria - Santana feat. The Product G&B vs. Thong Song - Sisqó
- I Knew I Loved You - Savage Garden vs. He Wasn't Man Enough - Toni Braxton
- Smooth - Santana feat. Rob Thomas vs. Kryptonite - 3 Doors Down
: I honestly thought d8uv
would fight me on this one. I remembered him saying he absolutely hated “Smooth”. d8uv
: My dad only listens to Classic Rock. So, when Santana came out with new music, of course he had to Limewire it, and he loved those singles. I heard “Smooth” so many times my teeth fell right out of my head. Turns out, it’s actually a great song. Who knew?
- Hanging by a Moment - Lifehouse vs. Where the Party At - Jagged Edge feat. Nelly
- Thank You - Dido vs. Again - Lenny Kravitz
- I'm Real (Murder Remix) - Jennifer Lopez feat. Ja Rule vs. It Wasn't Me - Shaggy feat. Rikrok
- Drops of Jupiter (Tell Me) - Train vs. Stutter - Joe feat. Mystikal
- If You're Gone - Matchbox Twenty vs. Hit 'Em Up Style (Oops!) - Blu Cantrell
- All for You - Janet Jackson vs. It's Been Awhile - Staind
- Let Me Blow Ya Mind - Eve feat. Gwen Stefani vs. Independent Women - Destiny's Child
- Fallin' - Alicia Keys vs. U Remind Me - Usher
: A garbage-ass year. I’m pretty sure I rounded third base listening to that Staind song, though. d8uv
: I thought Dido would win, since I love that song and still play it. antarris
: I think you mean “Stan”.
2002—Winner: “In The End”
- How You Remind Me - Nickelback vs. U Don't Have to Call - Usher
- What's Luv? - Fat Joe feat. Ashanti vs. U Got It Bad - Usher
- Wherever You Will Go - The Calling vs. Always on Time - Ja Rule feat. Ashanti
- Dilemma - Nelly feat. Kelly Rowland vs. Ain't It Funny - Jennifer Lopez feat. Ja Rule
- A Thousand Miles - Vanessa Carlton vs. Complicated - Avril Lavigne
- Hot in Herre - Nelly vs. The Middle - Jimmy Eat World
- In the End - Linkin Park vs. Blurry - Puddle of Mudd
- Foolish - Ashanti vs. I Need a Girl (Part One) - P. Diddy feat. Usher and Loon
: Hybrid Theory is the rare album that became better over time. antarris
: Seriously. I hated this in 2002. Love it now.
2003—Winner: “Crazy in Love”
- In Da Club - 50 Cent vs. Beautiful - Christina Aguilera
- Miss You - Aaliyah vs. Picture - Kid Rock feat. Sheryl Crow
- When I'm Gone - 3 Doors Down vs. Baby Boy - Beyoncé feat. Sean Paul
- Crazy in Love - Beyoncé feat. Jay-Z vs. Shake Ya Tailfeather - Nelly, P. Diddy and Murphy Lee
- Unwell - Matchbox Twenty vs. Get Low - Lil Jon & The East Side Boyz feat. Ying Yang Twins
- Get Busy - Sean Paul vs. 21 Questions - 50 Cent feat. Nate Dogg
- Right Thurr - Chingy vs. Bring Me to Life - Evanescence feat. Paul McCoy
- Ignition (Remix) - R. Kelly vs. All I Have - Jennifer Lopez feat. LL Cool J
: I had somehow never even heard “Crazy in Love” before. Wow. d8uv
: This did not win because it was novel. Lord knows, these pop charts are filled with random songs that we’ve forgotten. Almost every single one was forgotten for a reason. antarris
: To be fair, I think 2001 made me give up on pop music for like a decade.
2004—Winner: “Hey Ya!”
- Yeah! - Usher feat. Lil Jon and Ludacris vs. Slow Jamz - Twista feat. Kanye West and Jamie Foxx
- Hey Ya! - Outkast vs. Goodies - Ciara feat. Petey Pablo
- The Way You Move - Outkast feat. Sleepy Brown vs. Confessions Part II - Usher
- This Love - Maroon 5 vs. Slow Motion - Juvenile feat. Soulja Slim
- The Reason - Hoobastank vs. Tipsy - J-Kwon
- If I Ain't Got You - Alicia Keys vs. Freek-a-Leek - Petey Pablo
- I Don't Wanna Know - Mario Winans feat. Enya and P. Diddy vs. Lean Back - Terror Squad
- Burn - Usher vs. Here Without You - 3 Doors Down
: Outkast was as popular as they deserve, for once. antarris
: I was promised Enya. I got baby Adam Levine instead. What the actual fuck.
2005—Winner: “Gold Digger”
- We Belong Together - Mariah Carey vs. Mr. Brightside - The Killers
- Candy Shop - 50 Cent feat. Olivia vs. Don't Cha - The Pussycat Dolls feat. Busta Rhymes
- 1, 2 Step - Ciara feat. Missy Elliott vs. You and Me - Lifehouse
- Since U Been Gone - Kelly Clarkson vs. Don't Phunk with My Heart - The Black Eyed Peas
- Gold Digger - Kanye West feat. Jamie Foxx vs. Disco Inferno - 50 Cent
- Let Me Love You - Mario vs. Lose Control - Missy Elliott feat. Ciara and Fatman Scoop
- Boulevard of Broken Dreams - Green Day vs. Behind These Hazel Eyes - Kelly Clarkson
- Hollaback Girl - Gwen Stefani vs. Shake It Off - Mariah Carey
: That’s not even the best song named “Shake It Off.” d8uv
: Kanye can be very VERY good when he tries.
- Bad Day - Daniel Powter vs. Run It! - Chris Brown feat. Juelz Santana
- Ridin' - Chamillionaire feat. Krayzie Bone vs. SexyBack - Justin Timberlake feat. Timbaland
- Hips Don't Lie - Shakira feat. Wyclef Jean vs. Grillz - Nelly, Paul Wall and Ali & Gipp
- You're Beautiful - James Blunt vs. Over My Head (Cable Car) - The Fray
- Unwritten - Natasha Bedingfield vs. Be Without You - Mary J. Blige
- Promiscuous - Nelly Furtado feat. Timbaland vs. Me & U - Cassie
- Crazy - Gnarls Barkley vs. Check on It - Beyoncé feat. Slim Thug
- Temperature - Sean Paul vs. Buttons - Pussycat Dolls feat. Snoop Dogg
: “Crazy” vs. “Ridin’” was hard for me. I’m still not sure if I made the right call. d8uv
: Are you sure you weren’t thinking of the Weird Al version? antarris
: Yes. Fuck off.
- Irreplaceable - Beyoncé vs. This Is Why I'm Hot - Mims
- I Wanna Love You - Akon feat. Snoop Dogg vs. Say It Right - Nelly Furtado
- Buy U a Drank (Shawty Snappin') - T-Pain feat. Yung Joc vs. Girlfriend - Avril Lavigne
- Big Girls Don't Cry - Fergie vs. Makes Me Wonder - Maroon 5
- Before He Cheats - Carrie Underwood vs. Don't Matter - Akon
- The Sweet Escape - Gwen Stefani feat. Akon vs. Party Like a Rockstar - Shop Boyz
- Hey There Delilah - Plain White T's vs. Glamorous - Fergie feat. Ludacris
- Umbrella - Rihanna feat. Jay-Z vs. Smack That - Akon feat. Eminem
: Here it is, the weakest year of the tournament. There’s like one, maybe two good songs in this list.
90s Grand Tournament—Winner: “Under The Bridge” d8uv
: This was harder than the individual years, because we love every single one of these songs. “Under The Bridge” vs. “Nuthin’ but A ‘G’ Thang” was particularly brutal for me. antarris
: We started listening to high-quality versions of the songs here instead of just streaming YouTube. Coolio going over Ace of Base in my bracket surprised me.
00s Grand Tournament—Winner: “In The End” antarris
: “Umbrella” over “Crazy” and “Gold Digger”? Really? It’s like I don’t even know you! d8uv
: Should I pack up and leave? Maybe head to the train station? antarris
: I picked the song about choo-choo tr--oh, I see what you did there. Not cool. d8uv
: This song was always great, it just took a few years for people to forget the stank of nu-metal.
The Grand Final—Winner: “Under The Bridge” d8uv
: They tried so hard, and got so far. But, in the end, it didn’t even matter. antarris
: Afterwards, I looked up some of the history on “Under the Bridge”, and this makes sense. A funk-rock band wrote a song based on a poem and had it produced by Rick Rubin. It’s like catnip to both of us for completely different reasons. d8uv
: The thing that clinched it for me was the realization that this song builds so beautifully. It’s dynamic in a way most pop songs are, but maintains being interesting even during the subdued opening. antarris
: Yeah, I used an orgasm metaphor when I advocated for it. d8uv
: Most of the songs on this list were pop songs that became art. This song felt like art that became a pop song. That’s pretentious to say, so just remember—I almost went with “Umbrella”.
I chose these years because I needed to cut 4 years to get 20 years down to 16. Because of this, I excluded the two lowest-revenue (according to the RIAA, adj. for inflation) years from the 90s (1990 and 1991), and the two lowest-revenue years for the 00s (2008 and 2009). It might have been better to include them, but I didn’t want to.
Because the Billboard year ends in November, if a song is released during the winter, it’s likely that it won’t show up as a smash hit for one year; instead, it will show up as a mediocre hit across two years. Some songs can pull off charting highly in consecutive years, but that’s really rare.
It’s important to remember the wise words of Binary Star: Everything that glitters ain’t gold, and every gold record don’t glitter—that’s for damn sure
. The Hot 100 measures popularity, not cultural relevance or quality. A lot of very good, very important songs didn’t make the cut for this tournament, while a lot of long-forgotten dross did. Ultimately, I’m fine with this. Most of the fun of filling out the bracket was running into songs I don’t remember and going “What the fuck are YOU, song?”
For singles with an A-side and a B-Side (ex: “Follow You Down / Til I Hear It from You - Gin Blossoms”) I chose the first song. This is a little arbitrary, but a line has to be drawn somewhere.
Some additional caveats (because antarris
is an academic pedant): this obviously has too small and homogenous a viewing audience to be objective truth. While both of us have pretty broad taste in music, there are some genres—mainstream country and slow R&B in particular—that neither of us is super into. This probably skews our results significantly, especially in the 90s bracket.
Also, a better way to determine our sample of songs would be to take a page from Good Mythical Morning
’s cereal tournament and set up a poll for each year. However, getting a survey sample that’s representative of the population at large would be extremely challenging with an internet poll and, let’s face it, we’re not getting grant money for this shit.
If you disagree, you should fill out your own bracket: http://www.d8uv.org/misc/song-tournament-1992-2007.png
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