Figuring Out Kanye West’s ‘Greatest Song of All Time’

Casey Johnston, writing for Matter on Medium:

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.

I’m pretty against pop culture brackets as a thing (they’re starting to go away, thankfully, having been usurped by oral histories) but this one intrigued me because a. I’m always intrigued by anything KW-related; b. a woman wrote it; and c. I love reading stuff on Medium.

She did a pretty good job. My only quibble is that, in her quest to make sure she didn’t over-represent The Present Kanye tracks, she wound up with some early-round head-scratchers (‘RoboCop’ over ‘Mercy’?!). But by the end, two of the final four are two of my all-time favorites, and the winner is one of those two, so I can’t complain.

And on the web design point—read this thing on a computer screen. Awesome pictures, gifs, and audio samples of every song.