In 2010, Andrew Barber of Fake Shore Drive joined forces with Complex to drop a list of the best hip-hop songs in Chicago rap history. Then, Chicago hip-hop exploded, with one of the most commercially successful periods in its history. Many young artists were signed and gained national attention. We've adjusted the list to account for Chicago's recent changes, and adapted Andrew's list to account for the impact of a new generation.
Chicago. The Windy City. The Second City. The City of Hella Haters. Call it what you want, just don't call it a city that hasn't contributed to hip-hop's legacy. Often dismissed as a town buried within "flyover states" and a place where people only listen to house music, Chicago has a rich hip-hop history that dates back to the early '90s, when its two most prominent artists—Common and Twista—landed deals and released their debut albums.
Representing different sounds and different sides of town, these two kicked down the doors and ushered in a whole slew of innovative and unique artists who were making music differently than their counterparts on the coasts.
From the wild styles of Crucial Conflict to the laid-back, pimptastic sounds of Do or Die, Chicago was breaking through with slang and swagger unseen in other regions of the U.S. Years later, a boisterous up-and-coming producer would emerge as arguably the greatest and most polarizing rap artist of all time and change music completely. The City of Broad Shoulders, indeed.
Now, we easily could've made this list based on Kanye, Twista, Common, and Lupe records alone, but there's more to Chicago's story than just these four juggernauts. In the immortal words of No I.D., "the one that's in the middle is the one that sees the most." So come visit the Middle of the Map and take a ride down Fake Shore Drive for The 50 Greatest Chicago Rap Songs.
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