Wind city slickers: The five best rappers from Chicago

Where do the best rappers in the world of hip-hop come from? The obvious answer is the United States, but without being close minded, let’s pay some respect to the iterations of hip hop that have been growing in popularity abroad. 

The grime scene in the UK has seen the introduction of artists that have made waves beyond the shores of the relatively tiny island. Names such as Skepta, Central Cee and Dave, are known outside of London and Dublin these days. Whilst Latin American artists such as Bad Bunny, J Balvin and Daddy Yankee have been headline news in the music world for over a decade now.

Do any of these names hold a candle to what has come out of the East and West coasts of the United States? In fairness, probably not. Repping the East Coast, we have the likes of Jay-Z, Asap Rocky and Lauryn Hill, and on the West we have 2pac, Kendrick Lamar and Lil Kim. This is without mentioning what seems like the endless supply of hip hop talent flowing out of Atlanta.

An often overlooked city when it comes to hip hop is Chicago. We might have to blame Michael Jordan for claiming the city for basketball despite the efforts of the burgeoning music scene. In an attempt to bring them out of Jordan’s shadow, we’ve decided to rank the 5 best rappers to hail from the capital of Illinois.

The five best rappers from Chicago:

5. Polo G

Starting with a relatively new entry to the hip-hop game, Polo G seemed like he was always destined to do great things. His first track ‘Neva Cared’, went viral upon release. With projects titled Die a Legend, The GOAT and Hall of Fame already under his belt, you can be sure that he isn’t stopping any time soon. 

The very definition of a modern rapper who leverages the asymmetric capabilities that the internet can provide, G’s combination of melodic tone, vivid imagery and vulnerability ushers in a new, refreshing take on hip hop.

4. Twista

Twista’s prowess on the mic was overlooked slightly as, for a period of time, he was the world’s fastest English-speaking rapper. Consigning him more to pub trivia questions than concert halls. 

With this speed, though, he pioneered the “chopping” style of rap, which involved stitching together bars at such a pace that a verse could be confused with the sounds of an automatic weapon or a helicopter. How many rappers can claim to have created their style? Not many.

3. Juice World

Similar to Polo G, Juice Wrld leveraged melodic beats, which could be classified as dreamy, and introspective lyrics. Gone are the days when rappers only produce content about money, sex and violence. The late rapper would touch on themes that he felt were not spoken about enough in the music industry.

Before his death, at just 21 years of age in 2019, the man formerly known as Jarad Anthony Higgins had claimed the praise of hip-hop legend Eminem, who spoke on the Crooks Corner podcast following the former rapper’s death. 

“That kid was so talented, man,” he confirmed. “His freestyle that he did on Westwood where he rapped for an hour, like what the f**k! He might have been mixing a little bit of written in there, but that’s the sh*t that we tried to do at the hip hop shop, was work on our freestyle right? But to be able to slip in and out of written when you need to, you know what I’m saying. If you’ve got a certain punchline to take out this dude. To be so young, he mastered that so f**king quickly.”

2. Chief Keef

Whilst Twista might have created a style of rapping, Chief Keef has a solid claim to creating a new subgenre of hip hop. Synonymous with the US drill scene alongside pop smoke, many other hip hop artists have cited Keef as influential to their styles.

His DIY approach to music production was revolutionary as he produced and recorded his own music without a label. Former Interscope A&R, Larry Jackson had this to say about how the game was revolutionised by these methods, “There was nobody who had the kind of gravitational pull he had online. He was the first.”

1. Kanye West

Was it ever going to be anyone else? It is hard to define the greatness of the man who has possibly done more for the proliferation of hip hop than any other artist. With a genuine claim to having produced the greatest album of all time in My Beautiful Dark Twisted Fantasy, amongst other instant classics, Kanye is simultaneously an icon and an enigma. Trying to pick just one song to define his career would be painstaking.

Yes, he was probably wrong for interrupting Taylor Swift’s acceptance speech at the Grammys. Yes, he was definitely wrong for saying that slavery was a choice. But, given his self-proclaimed position as a “21st-century schizoid man”, this may be one of the rare cases where we can separate the art from the artist. 

One might be able to question his character and for a good reason. However, what is unquestionable is his work ethic in producing music, which has altered his perception of what was possible. He is a generational talent.