Grantland’s Best Song of the Millennium Bracket

There are many reasons why I love the website Grantland; the brain child of ESPN’s Bill “the Sports Guy” Simmons, it brings together a lot of thoughtful and interesting contributors to write about the worlds of sports and pop culture. These are worlds that I like to spend a lot of time in, so I am frequently checking in on the blog to see the latest and greatest. I partially blame writer Alex Pappademas for my backslide into once again watching Keeping Up with the Kardashianshis recaps are so funny that I decided I had to see the ludicrousness that he was chronicling for myself. I am not proud of this. Andy Greenwald has become one of my favorite TV critics and I often borrow their stories or links for my pop culture roundups.

However, one of the main reasons that I love Grantland is their affinity for putting things into bracketed tournaments. Regular readers of my blog will recall that I love brackets. In my opinion, anything done in a bracket format is instantly more interesting. There’s just something about pitting two different things against each other that makes debating things more fun. I think the bracket format is half the reason that the NCAA men’s basketball tournament is so popular. The bracket simply serves as a great organizational tool to determine what is the “best.” Grantland has done brackets for all sorts of things, from the greatest character on The Wire to the most hated college basketball player to the best soup (dubbed the “souper bowl”). These are my people.

Now, “best” is in quotation marks because obviously a lot of this stuff is subjective; when you take brackets out of actual sports competition, it all becomes based on people’s opinion and most popular often trumps truly the best (whatever that means – it would vary person to person). So while it is awesome when the thing you prefer or love advances in this type of pop culture tournament, you kind of have to take that victory with a grain of salt. We’re not finding definitive answers here. Except that Omar is the greatest character on The Wire. That right there is gospel.

So when Grantland unveiled their latest bracket – The Battle for the Best Song of the Millennium – I was naturally intrigued. If I am being honest, I have probably been following the ups and downs of this bracket more than the unfolding crisis in Syria. I may be a terrible citizen, but I’m a great pop culture connoisseur.


Now music has never been one of my strengths; I listen to a lot of music, but I tend to like what I like which doesn’t always match up with critical acclaim, popular opinion or actual quality. I always have to laugh when I play the “worst songs” category on SongPop, since I personally like 99% of the songs that they seem to think everyone accepts as terrible. Except Nickleback – I’m with you people on them. I was way more into music back in high school and college, simply because I had a lot more free time back then. Sadly, my heyday of musical knowledge predates the beginning of the millennium by a few years; this is actually the era of music that I am the weakest on. Between the proliferation of music sharing and just the internet generally along with the fact that graduate school and working just didn’t leave a lot of leisure time, a lot of music that happened from 2000 on that I’m just not that up on. There just was too much to keep track of. I wasn’t completely oblivious and I’m definitely more aware of new bands today than I was five years ago, but it’s still a dark period for me. I’m a lot more confident of my knowledge of the 80s and 90s and probably even the 70s.

I am really terrible with song titles, so at first glance I was surprised at how many of these songs I didn’t know. However, some Google exploration resulted in the paring down of the number of songs that were completely unfamiliar to me. Still, it was a reminder that I had fallen behind for a decade or so, especially in the world of rap and hip hop (which I used to be pretty up on back in the day). Being aware of the existence of T.I. and Lil Wayne apparently did not translate to me actually knowing any of their songs.

Still, even if this musical era isn’t in my wheelhouse doesn’t mean that I wasn’t curious and didn’t have opinions. The Grantland bracket wound up playing out like this:


I wouldn’t have predicted their ultimate winner – Outkast’s “Hey Ya” – at the beginning of this process, but after giving it some thought it does kind of make sense. There were a lot of tough choices in their brackets and there were what I would consider some upsets. I think that there were some VERY big omissions. But when your final four includes “Hey Yeah,” Adele’s “Rolling in the Deep,” Kanye and Jay z’s “Ni**s in Paris” and The Killer’s “Mr. Brightside”…….


I have to say, as I pursued their list, it was fairly representative of the last 13 years of music. Their brackets featured more diversity than I would have expected and crossed many genres. These people had been paying way more attention to music than I had, so I have to defer to their opinions to some extent. That doesn’t mean, however, that I 100% agree with all their selections. While they certainly captured many of the songs that would have been in my bracket, some of my personal picks were not represented.

The songs in the Grantland bracket were the result of a collaborative process: each contributor came up with their slate of 25 songs released as singles from 2000 to 2013 and then the group voted on all the candidates. Apparently the discussions got pretty heated and it has been fun to listen to the contributors on their various podcasts bemoaning that their favorites didn’t make the cut.

So, taking all of this with a tremendous grain of salt, I humbly present what would have been my slate of candidates for song of the millennium (had anyone asked – and they didn’t). These are in no particular order and some may have been disqualified since I can’t guarantee that all of these were released as singles:

  1. Ignition – R. Kelly
  2. The Dog Days are Over – Florence + the Machine
  3. Oxford Comma – Vampire Weekend
  4. Power – Kanye West
  5. Bye Bye Bye – N’Sync (deal with it people)
  6. Seven Nation Army – The White Stripes
  7. Teenage Dream – Katy Perry
  8. Rehab – Amy Winehouse
  9. Rolling in the Deep – Adele
  10. Single Ladies – Beyoncé
  11. Lose Yourself – Eminem
  12. We Found Love – Rihanna, Calvin Harris
  13. Poker Face – Lady Gaga
  14. Cry Me a River – Justin Timberlake
  15. Toxic – Britney Spears
  16. Yeah! – Usher, Lil John, Ludicrous
  17. How to Save a Life – The Fray
  18. Hey Ya – Outkast
  19. Call Me Maybe – Carly Rae Jepsen
  20. Since U Been Gone – Kelly Clarkson
  21. All My Life – Foo Fighters
  22. Izzo – Jay Z
  23. New Slang – The Shins
  24. Your Body is a Wonderland – John Mayer
  25. Crazy – Gnarls Barkley

Of course, this list could change at the drop of a hat and I’m sure with some further deliberation I might swap out some songs for others. These aren’t necessarily my favorite songs of the last 13 years, but these are the songs that I think of when I think of this time period. I limited myself to one song per artist, which made for some difficult choices. I don’t know that all of them would have even received serious consideration – a lot of people hate “Your Body is a Wonderland” and John Mayer generally, but I am not one of those people – but I don’t think any of these are completely out of left field. The list is a little heavy on the pop, but otherwise a pretty solid snapshot of 2000-2013.

What songs would make your bracket? What songs did Grantland and I miss that you think deserve consideration? Sound off in the comments below

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s