"It was this jaw-dropping moment ..."

A Short Q&A With Cole and Charles:

Cole: Because Charles has been giving some wild music takes without repercussion for far too long. Someone needs to call him out on his bullsh-t. (I also respect Charles immensely, but don’t tell him I said that.)

Charles: I vehemently disagree with Cole about most things regarding musical taste. He’s the Skip to my Stephen A., the oil to my vinegar, the Kendrick to my Drake, which is great fodder for a podcast and taxing on our friendship. It also doesn’t hurt that despite our contentious relationship, Cole teaches me something new about music every time we talk.

What about this format excites you?

Cole: Mostly I’m just excited to argue with Charles. But also the exercise of determining an artist’s single best song forces you to scrutinize their music in a way you normally wouldn’t. A number of factors must be considered: musicality, lyricism, message, popularity, how it performs live. Being forced to examine every song by these measures has been very fulfilling.

Charles: There’s no hiding with this format. You have to stand on your word. Each episode there’s a Last Song Standing, which means feelings will get hurt. The moment Cole admits “Swimming Pools” aged like milk is a revelation.

Why do the first season on Kendrick Lamar?

Cole: With a lot of artists, it’s clear what album or song is their strongest. With Kendrick, he has so many great albums and songs that it’s a near-impossible task to pick just one as his best. I’m also a Kendrick Lamar truther—I think he’s the greatest rapper of all time. Charles, of course, does not agree. So I’m looking forward to convincing him through this first season.

Charles: Kendrick Lamar is an album artist. Some of his greatest songs make very little sense out of context of a larger body of work. Similarly, Kendrick’s hits don’t always paint the totality of what makes him an interesting figure. The level of thought it takes to pick the best Kendrick song week after week is a layer of tension you can’t find with many of his peers.

Why are you confident that your pick will be the Last Song Standing at the end of the season?

Cole: I’ve done over 40 episodes analyzing Kendrick’s music on Dissect, so I’m coming into this season with that up my sleeve. I also have a background in music theory and composition, which I’ll be using to my advantage. In short, Charles stands absolutely no chance.

Charles: I go to war every week on The Midnight Boys. My heart was forged in the content mines. Cole ain’t ready for a generational hater like me.