What Rappers Would You Pick for "Chicago vs. Everybody?"

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And so we've come, to the end...of, the road.

Here's the deal people. So far in this "vs. Everybody" series I've tackeld L.A., Atlanta and New York City. It feels like I also need to do Chicago, so today I'll be heading to the Windy City. I'm thinking this will be the end the series, but if there's another city (what's good, Topeka?!?!") that y'all absolutely insist on, I'll consider coming out of retirement and doing it. So with that said, welcome to the Chi.  

First, for those who are new, or regulars who had their memory erased in a tryptophan overdose, let's go over the rules again real quick. For those who really want the fine print, the ridiculously detailed rules are here

  1. Hey, "Detroit vs. Everybody." That was cool. What if we picked out a roster for every city? [Note: We already did LA and NYC and ATL.]
  2. You get to pick four rappers to rep the city, plus one hype man who doesn't rap a verse but can yell stuff throughout the track (aka the DH). 
  3. You're not necessarily looking for the "best" rapper, but you're not necessarily looking for a battle rapper either. You're looking for someone who's so aggressively, shockingly dope other cities would be scared to go against them. Hence the "vs." 
  4. They have to be alive, and you're getting them as they are now. (ex. You'd be getting Animal Ambition 50 Cent, not Get Rich or Die Trying 50 Cent.) 

Got it? Good. Now let's move onto the specifics. 

I won't front, I'm a little nervous about this one. Chicago is one of those cities that's its own world. Over the years I'd like to believe I've picked up a pretty good amount of Chicago knowledge, and I consulted Chi-native DJ Z, but especially now that the city seems to be experiencing a hip-hop rennaisance, I could easily see some Chicago residents taking shots at me for not including so-and-so. But whatever, if I didn't write things because I was worried the internet would say mean things, I'd never write anything. Let's do it. 

So Who's on Chicago vs. Everybody?

Bump J (DH): I won't lie, I'm not particularly well-versed in Bump J, but I do know that everyone I've ever talked to from Chicago ever swears that Bump J is that dude who was going to make it but had his path derailed. (Case in point, Yeezy's shout out.) So come on; I live in Cali and even I know a prison-phone recorded intro from Bump wouldn set this shit the fuck off. 

Kanye West: Even Jim Harbaugh's angry about this pick, and he's from Michigan. 

Listen, I know mentioning Kanye's name in 2014 is the quickest path to controversy on the internet, but I still don't see any world in which Ye isn't on this song. He's by far the most famous artist from Chicago on the planet now, he does rep his city (even if his relationship with the Chi is complicated) and the man can still rap. Plus, there really aren't many people on the planet better at boasting than Yeezy, this is the kind of song he was born for. Every city has at least one automatic pick, Kanye is Chicago's automatic pick. 

Chance the Rapper: We're only on the second selection and Nathan's already losing his mind!!!

Yeah, fair enough imaginary people in my head who are angry about this pick. I hear you. Chance isn't nearly aggressive enough - there's a good chance he could spend his entire verse talking about his grandma over a flute solo. If I didn't pick Blu for the L.A. version because I thought he wasn't right for this kind of track, how could I pick Chance here? All great points, but allow me my rebuttal. First, like every city, I want a mix of veteran and young voices in here, and right now Chance is his city's most prominent young voice. Second, he's a huge wild card. Yes, he could absolutely ruin this song, but there's also the chance he could come up with some astoundingly brilliant shit no one would ever think of. Putting him here is a huge gamble, but I'm a gambler at heart. I'm willing to take the risk. 

Lupe Fiasco: Sweet baby Jesus, I honestly didn't expect Chicago to be this hard. No joke, I just spent the last 20 minutes staring at my computer screen before I typed the words "Lupe Fiasco." 

Even just a few months ago I don't think I would have been able to place Mr. Fiasco here. I don't want to say he'd falled off, but he'd certainly been stumbling. But the man's been on a hell of a streak lately, and when it comes to tackling some of the complexity surrounding violence and poverty - unfortunately two things that have become Chicago's strongest associations - he's not going to shy away. I'm willing to bet that given the stakes (a national rap battle for city supremacy) Lupe would bring his A-game and absolutely destroy this.  

Chief Keef: Hello? Is this the FBI? So, tell me about that witness relocation thing you guys do. 

I swear I'm not trolling here, and I'm pretty nervous about putting in Keef. DO YOU HAVE ANY IDEA HOW MANY OTHER BETTER EMCEES THERE ARE IN CHICAGO, NATHAN?!?!?! I mean, fucking come on. You're going to leave out vets like Common and Twista? You're going to pretend like Mick Jenkins isn't one of the best young voices to come along in years? And for what? For a kid who might not actually know what a rhyme is? (For some reason I'm doing a lot of talking to myself in the third person today.)

If this was a "best rapper" discussion, Keef might as well not exist. But after a whole lot of thinking, after more marinating than a barbecue contest, I felt like Keef was perfect for the purposes of this track. First, it just didn't seem right to ignore the drill scene. Love it or hate it, in many ways it's the sound of the city in 2014, and Keef is its forerunner. Second, the symbolic value of having Keef AND Chance (the two ends of the new generation spectrum) AND Lupe (who he's had beef with) AND Kanye (again) would elevate this from a song to a historical moment. Put together, like some sort of rap Voltron, these five represent the full range of Chicago's hip-hop past and present. 

Alright DJBooth Nation, feel free to grab your pitchforks and burn my (internet) house down, I can take it. But I promise I didn't take this lightly, and looking back on it in a lot of ways I'm really happy with this line-up. Chicago stand up. 

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[Nathan S. is the managing editor of The DJBooth and a hip-hop writer. His beard is awesome. His Twitter is @RefinedHype.]