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Kanye West · S1 E5
South Side
Chicago's hip-hop scene in the 90s, and the teenager trying to break in
A basement studio on the South Side, 1995. A seventeen-year-old Kanye West plays a beat for a room full of rappers and nobody looks up from their conversation.
"Touch the Sky" ft. Lupe Fiasco (2006). Two kids from Chicago who made it out. The video is a rocket-fueled fantasy about ambition, but the real story is two South Side teenagers who refused to accept that their city couldn't produce superstars.
The Third Coast
In the mid-1990s, Chicago is hip-hop's overlooked city. New York has Biggie, Nas, and Wu-Tang. LA has Tupac, Snoop, and Death Row. Chicago has Common, Twista, Do or Die, and a scattered underground scene with no major label infrastructure and no national spotlight.
The South Side, Chicago
The sprawling stretch of neighborhoods south of downtown where Chicago's hip-hop scene lived: basement studios, open mics at the Wild Hare, cyphers in parking lots, and record shops where kids dug for samples.
“Chicago didn't have a sound yet. That was the problem and the opportunity. There was no blueprint, so you could make one, but nobody was paying attention while you did it.”
— GLC (rapper, Kanye's childhood friend), interview with Complex, 2012
Touch the Sky, Kanye West ft. Lupe Fiasco (2006)
Built on a Curtis Mayfield sample from "Move On Up," this track is pure Chicago. Mayfield is the city's soul music godfather, and Kanye chopping his horns into a hip-hop beat is a direct line from the South Side's musical past to its future. Lupe Fiasco's guest verse is critical: he represents the next wave of Chicago rap that Kanye helped open the door for. Listen for the way the sample builds across the song, adding layers of horns and strings until the final chorus becomes a full orchestral moment.
TAP TO REVEAL: Why didn't Kanye fit into Chicago's rap scene?
The Producer's Trap
Here is the problem Kanye keeps running into: everyone wants his beats, but nobody wants to hear him on the mic. In the '90s, producers produce and rappers rap. Kanye does not accept this division, and that stubbornness defines the next decade of his life.
Bonus Listening
"Drive Slow" ft. Paul Wall & GLC from Late Registration (2005). GLC is Kanye's childhood friend from the South Side, and this track is a slow cruise through the streets they both grew up on. The Hezekiah sample drips with nostalgia, and GLC's verse is pure Chicago storytelling.
Which Chicago rapper was one of the first established artists to support Kanye?
Kanye is stuck: he can make beats better than anyone his age, but he needs someone to teach him how to turn raw talent into a career. Next: the Chicago producer who takes one listen and says, "Come to my studio tomorrow."
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