Top 5: The five best rappers to ever come out of Chicago
(Credit: Wikimedia/Hip Hop Hero)


Top 5: The five best rappers to ever come out of Chicago

From New York to to Los Angeles, every metropolitan city in the US has produced its fair share of rappers and Chicago is no exception. The third most populous city in the US, ‘The Windy City’ has given hip-hop culture some icons and even amazing subgenres such as hip-house in the 1980s and more recently drill.

The latter was said to be pioneered and popularised by the rapper Chief Keef who has been a highly elusive and controversial figure in hip-hop. Here we’re picking out five of the greatest rappers to ever come out of Chicago.

Chicago was not the first or even the second city to get accepted into hip-hop. New York was, of course, the mecca of hip-hop during the 1980s. However, it was a culture that was most prominent on America’s Eastern seaboard, particularly in the North. New York, New Jersey and Pennsylvania with their respective cities such as New York City, Newark and Philadelphia being the areas spearheading the genre.

During the ’80s and even the ’90s Midwestern America was a hub for house music with cities such as Chicago and Detroit very much being at the centre of pioneering underground house and techno scenes. However, eventually, the city did start to produce some hip-hop superstars. Chicago is quite similar to New Orleans in that it doesn’t produce rappers very often but when it does they are absolutely phenomenal.

So in this article, we are going to look at the best top five rap artists to ever come out of Chicago.

The five best rappers to ever come out of Chicago:

5. Earl Sweatshirt

A former member of the legendary LA-based crew Odd Future, Earl Sweatshirt is one of the few rappers that managed to gather enough of a cult following while in the crew that he could sustain a solo career after the crew’s dissipation. The rapper, despite being part of Odd future was actually born and raised in Chicago and moved to California for college. His rapping ability was on par with every other member of the crew and he was just as creative.

Earl Sweatshirt, akin to Tyler The Creator and Frank Ocean, was able to gather a separate following while still in the crew for several different reasons. Not only was his name bizarre and comical, but he also had a unique look. Some may have described him as ‘goofy’ or maybe even a bit ‘dopey’ looking, but that was part of his appeal. He was preppy, perhaps slightly nerdy, but this, combined with the fact he was a rapper, was refreshing for many who were sick of the macho gangster aesthetic.  Ever since Odd Future, Earl Sweatshirt has been making music, and his core fanbase has never left his side. He is experimental, daring and audacious with his music.

4. Vic Mensa

Born to a Ghanaian father and Caucasian-American mother, Vic Mensa grew up in the Hyde Park neighbourhood of Southeast Chicago. Mensa’s career beginnings go back to 2009 when alongside a friend he formed a small crew called Kids These Days. With a positive dynamic between the group, they would go on to release an EP in 2011 called Hard Times and then a full mixtape called Traphouse Rock which performed quite poorly on the website DatPiff.

Following this, the rapper decided to go solo. Deciding to head in a different and more audacious style creatively Mensa uploaded his debut solo mixtape Innately in 2013 and much to his surprise it was received extremely well on DatPiff and received a copious amount of downloads. Following this local success, he would go on to open for acts performing in Chicago including the likes of J Cole, Danny Brown and Wale. As a result of this exposure and growing popularity, Mensa would go on to sign with Roc Nation in 2014.

3. Chance The Rapper

Chance The Rapper rose to fame at a similar time to the likes of Tyler The Creator, A$AP Rocky and Yung Lean during the early 2010s. Coming out of Chicago, Chance The Rapper is often cited as the best Rapper of recent times to come out of the city.

Chance the Rapper (real name Chancellor Bennett) came up like most rappers through mixtapes. Bennett had an organic come-up in his hometown and was quick to appear on Chicago’s hip-hop radar. In 2011 he released his debut mixtape entitled 10 Day. The project made a lot of noise locally, as Bennett had tirelessly networked in and around Chicago in order to reach producers and fellow underground rappers prior to its release.

Following its local success, with over half a million downloads on DatPiff, he was named on Complex magazine’s ’10 New Chicago Rappers to Watch Out For’ list. Following this exposure and the success of his first mixtape, he was asked by Childish Gambino not only appeared on his sixth mixtape but also toured with him.

2. Common

Common is one of Chicago’s first success stories. With his career origins in the mid-’90s Common is known for his lyrical ability and extremely conscious lyrics. He is also renowned for having a very soulful and jazz-inspired type of sonic. The rapper is also a known poet.

Unlike previous rappers mentioned Common did not come up through mixtapes but put out a series of albums independently that did very well in Chicago and New York on an underground level operating in the same space as artists such as Mos Def, Talib Kweli and Black Thought. Behind the commercial Gangsta and Mafioso rap movements in the ’90s was a more underground, conscious and soul-based form of hip-hop.

Along with neo-soul artists bringing awareness to issues surrounding Africa and the Five per cent nation movement, these artists came together forming a collective known as The Soulquarians. The term also became a fast and loose way of describing a type of music that fell within the realms of conscious neo-soul and hip-hop at the time. Common broke through to the mainstream with his J Dilla-produced album, Like Water for Chocolate. Released in 2000 it did not even enter the Billboard 200 yet was so good, the album’s second single ‘The Light’ received a Grammy Award nomination for ‘Best Rap Solo Performance’.

However, Common’s biggest album to date was his 2005 album, Be. Executively produced by Kanye West, the album debuted at number two on the Billboard 200 and was certified Gold by the RIAA.

1. Kanye West

It was the obvious and only right choice to make. Kanye West is the most successful and revered rapper to come from Chicago. He is the wealthiest man in hip-hop and is just one of two self-made billionaires in the genre. Since his emergence on the Chicago underground hip-hop scene in the late 1990s, West has gone on to work with all the greats in the business.

When West first entered the game, he was seen as strictly a producer and had to fight against the industry to become what he is today. Even Jay-Z has previously admitted that he was not keen to sign West as a recording artist and originally had only planned on offering him a producer deal. However, with a bidding war between labels for West, with Ye’s only demand that he be taken on as a recording artist, with the risk of losing his talent to another label imminent, Jay and Dame Dash agreed to West’s terms and gave him a record deal.

The musician, fashion designer and entrepreneur is widely considered a genius. His impact on the sound of hip-hop is unparalleled, and although other artists such as Pharrell have shifted the sonics of hip-hop during their career, none have shifted it to the extent that Kanye has.

Aside from all the rants and craziness (like his recent appearance on InfoWars), West is the most influential figure in hip-hop without a doubt and, on numbers alone, obliterates almost every single rapper in hip-hop with regard to sales and overall accumulated wealth. Elusively and erratically emerging from his Wyoming studio with new projects and creative visions, whether it’s to do with fashion, music or other, people turn their heads and invest in what Kanye West produces and sells.

Whether or not he is a good person, while separating art from the individual, it is impossible to deny that Kanye Wet’s music is not good and that whether or not he is a clever politician, with regard to music, he is an idiot-savant.