The most labor-intensive, compulsive, and scientific way to determine the Greatest Kanye West Song of All-Time. (And, in the process, hopefully figure out why he means this much to me).

By Casey Johnston

In the spring of 2004, a girl on my high school lacrosse team wearing her uniform of a kilt and polo shirt dropped into a seat next to me on the bus on our way to a game and said, “Here, you have to listen to this song, it’s so funny.” It was “The New Workout Plan.” There, I had the whitest possible introduction to Kanye West.

The College Dropout, Kanye’s first album, was released 11 years ago, and I never could have guessed how he would evolve over the next decade, how integral he’d become to how I live. Kanye is not just content or an artist, he’s a mindset and a way of being.

It’s funny: Kanye is known for his bombastic overconfidence, but so much of his music is about laying bare his insecurities. He has a lot of modes: He’s arrogant, emotional, clever, regal, desperate, dazed, dismissive, self-assured, self-aware. A few months ago, I decided I wanted to find a systematic way to process him, his body of work, and what he means to me.

There are album reviews, which is how Kanye is usually processed, but they don’t show him fully in context. Ranking also doesn’t work , for reasons mentioned above: He’s changed too much and his work is too varied. So I made a bracket, and through this bracket, I’ll find my favorite song. Theoretically.

Methodology

I chose the initial set of 32 ad hoc, and then refined it by re-listening to all of the albums and swapping out this or that song while keeping a list of alternates. My loose goal was to represent all albums, with some effort toward representing them all somewhat evenly. This didn’t pan out, as The College Dropout has six songs in the set while Graduation has two. I decided to have Watch the Throne and Kanye West Presents GOOD Music Cruel Summer in the mix, because, while they are not his solo releases, collaboration is essential to Kanye’s work. It feels disingenuous to say I can include, for instance, “Monster,” but can’t include “No Church in the Wild.” His most recent releases (“Only One,” “FourFiveSeconds,” “Wolves,”…