Kanye Madness: The Intro

“Beware the Ides of March.”

Shakespeare’s chilling warning for the world’s most powerful leader perfectly encapsulates the feeling that shourds the third month of the year.  Appropriately named for Mars, the Roman god of war, only one word can properly describe March: Madness.

As a time of transition between winter’s barren cold and spring’s lively warmth, March is left a mess of winds, sunshine, and rain. Between devout Christians abstaining from meat, to college kids frenzied in a drunken stupor during St. Paddy’s day, March can get a little insane.

For sports fans, this manifests in the NCAA’s 64-team basketball tournament aptly known as March Madness.

Now personally, I am not a big fan of the college basketball aspect.  I am, however, a very big fan of the madness.

Fortunately for me, radio host Carrington Harrison took the March Madness style competition and combined it with the person who may embody the meaning of March the most: Kanye West.

Just like March, Kanye is unpredictable, entertaining, erratic, and quite frankly, kinda crazy. And this makes him the perfect subject of a March Madness style bracket. With a plethora of songs that range in sound, meaning, tone, and purpose, Kanye’s discography makes for a compelling and competitive knockout tournament.

And at the heart of the tournament is the following question:

“In your opinion, what song can be considered the greatest Kanye West song of all-time?”

I worded the question like this for three reasons:

1) “In your opinion …”

At the end of the day, each individual will have their own answer , which is formulated through a unique way of thinking, understanding, and personal emotional experiences.

2) “ … can be considered”

There is no one correct answer – rather, the winner most accurately satisfies the above question (though other choices may work as well).

3) “… greatest Kanye song of all-time”

As opposed to using the word “favourite” which suggests pure subjectivity, greatest suggests elite distinction in all facets of music (ie. musically, personally, historically, culturally).

Cover art from Kanye’s full-length albums (image via steemit)

Because I’m a big nerd and take these fun thought experiments super seriously, I have created the following criteria to help me answer the tournament question.

Judging Criteria:

The “One Hundred Times Test”

Quite simply, out of 100 times, how many times would I choose to listen to Song A over Song B?

In its most basic form, this is a quick and easy way to figure out which song is musically preferred. As well, by assuming 100 listens, I control for variances in mood or any other chance variability. Let me explain why this is important.

When doing research and re-listening to all the songs in this tournament, I stumbled upon the infamous “I’mma let you finish …” moment where Kanye interrupted Taylor Swift’s award acceptance. The next day, as I was sitting in the car queuing Kanye songs to play for a drive, I suddenly stopped. I sat there and thought to myself “SCREW IT. I’m going to jam out to some Taylor Swift for the next 20 minutes.” And so I did.

It was a pretty nice day outside, so I was driving shotgun with my hair undone in the front seat of my car, blasting “Our Song” with my windows open. I pulled up to a red light at the same time as another car who was also blaring music. The driver was playing “Hypnotize” by Biggie Smalls. We made eye contact, acknowledged each other with a nod, and drove off.

99 times out of 100, I would be the one pulling up, playing The Notorious B.I.G., but for that one moment in time, I was the guy playing Taylor Swift.

This test that can be applied to anything and it will usually give a definite answer.

For example: 100 out of 100 times, I will choose to eat a real burger over a vegan “burger”.

Other times, it might be a little closer.  

For example: If you asked me to choose between a Big Mac and a Whopper, I’d probably say 58/42 in favour of the Big Mac, but it’s not a clear cut decision.

In the case that pure sensory stimulation does not produce a runaway winner, we move onto Criteria #2 …

Personal Connection

When there isn’t an obvious choice at the superficial level, the next step is to go a little deeper.

If both options satisfy sensation (in the case of this tournament, the sense of hearing), how something resonates on a personal level is the next standard of measurement.

For example:

Back in the good ole’ days, I was forced to write and do assignments with something called a pencil. For those who do not know what that is, I have inserted a picture below.

This is a pencil.

Pencils are relatively cheap tools. They are easy to replace and quite dispensable. I remember, however, consistently using the same pencils until they were too small to physically hold and write with. Rather than get a new one that would serve the exact same purpose at the same level of efficiency (and probably more comfortably too), I would choose the same old pencils.

Over the thousands of words each stick of wood would pump out for me, I had built a bond with them.

(As I tell this story, I am now realizing how crazy it seems, but I can’t be the only one that has special bonds with inanimate objects?)


Anyway, if my ears enjoy listening to both songs equally, I will choose the song that is closest to my heart.

If I happen to have a strong connection to both songs, we move onto Criteria #3 …

Importance to Kanye

This does not mean how important the song is to Kanye himself, but rather, the song’s significance to his artistry and overall legacy. Allow me to clarify.

“Juice” was the first single from Chance the Rapper’s breakthrough mixtape “Acid Rap.” It quickly became of one his most recognized songs and arguably sparked his entry into mainstream popularity. However, Chance has gone on record to state that at this point, he hates the song, due to it being continually requested. Yet, it remains one of the most important songs in his career.

In respect to Kanye’s greatness, if I enjoy listening to two songs equally and they both resonate with me on a personal level, the tie-breaker will come down to each song’s cultural and historical significance.

“Trade the Grammy plaques just to have my granny back.” (image via The Atlantic)


Sorry for the super long set up, but ‘tis the inner workings of my mind. Man, we haven’t even gotten to the songs yet!

In order to do the matchups justice (and so you don’t have to sit through my rambling for much longer), I will be releasing the tournament in several parts.

Click here to read First Round (Part 1).

Stay tuned for the rest of the tournament!