Who’s the Greatest Chicago Rapper of All-Time? Posted by Nathan S. on 02/05/14 | Filed under Top Stories, Debates, RH Nation Answers, City Series

And it don't stop. After covering NYC, LA and ATL, this week I turn our ongoing "City Series" to the Midwest with the allmighty Chicago. So far RefinedHype Nation has Andre 3000 as the greatest from Atlanta, Tupac as the greatest from L.A. and Nas as the greatest from New York. Who will grab the crown for Chicago? 

As a reminder, here are the guidelines for defining "Greatest From That City": 

Inherent Dopeness: In a vacuum where record sales and influence don't matter, how purely/rawly dope are they? If you could only listen to one rapper from that city until the day you died, who would you pick? If there's a national rap battle, best song wins, who are you picking to represent that city? 

Influence: When they did something, did the rest of their city follow? And by extension, did the rest of the country follow? Have they proven they can have multiple generations of influence? 

City Association: The two above are pretty standard criteria for any RefinedHype debate, but this is the x-factor in the "City Series" - how closely is that rapper linked to his/her city? For example, if I say "Toronto hip-hop" a lot of people's strongest association is going to be with Drake. (It's an example, relax, we'll get to the Toronto-specific debate in due time.) By contrast, while Tupac's roots are Bay Area, he also has some really strong associations with L.A. (Again, we'll get there.) Point it, the greatest rapper from that city has to really embody and represent that city. 

Got it? Now, onto the nominees for a city that's produced an astounding amount of dopeness. 

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Yung Berg: Relax Harbaugh, that was a joke. 

Kanye West: The most complicated nominee because when is anyting involving Kanye ever simple. Even setting aside the four million hours of debate we could have about his inherent dopeness, his city association is complex enough that he's written several songs about it himself. All that considered though, I have to give him the top spot. 

Lupe Fiasco: Although also one of the most confusing emcees to ever grab a mic, there's no doubting that at his best, Lupe is one of the greatest lyricist of all-time period, let alone one of the greatest from Chicago. And he's remained Chicago to the core. 

Common: The younger generation may know him primarily as an actor, or that old guy Drake had beef with, but for those in need of a refresher, we're talking about multiple classic albums (and classic songs) over a 24-year career that's included work with other Chicago staples like Kanye and No I.D. Plus a huge city association score; I have him just behind Kanye, ahead of Lupe (and everyone else). 

The Young Guns: A new generation is currently bringing Chicago hip-hop back into the spotlight. I don't think any of them - from Chance to Keef to Vic Mensa to everyone else who deserves a mention - have done enough yet to really be a factor here, but they're certainly building the foundation to become all-time greats, especially Chance. Salute to them. 

One last word before we get to voting and discussing. I know in the age of Wale screaming at Complex we're used to a site putting up a definitive, unchangeable list and then yelling at them. This isn't that. This is more of one of those collaboration type deals. I won't claim to know Chicago nearly as well as a Chi-Town native.

So if you're from there and you think Crucial Conflict deserves a place in the discussion, or the number one spot, add them yourself and make the case. The same goes for Twista or Do or Die or GLC some other artist that I don't even know about but is a legend in the Chi. 

And with that, have at it people.  

Who's the Greatest Chicago Rapper of All-Time? ;