It’s hard to remember now what Chicago used to be talent-wise before the emergence of Chance the Rapper, Vic Mensa, Chief Keef and Lil Durk. But, not long ago, Chicago was hardly known for producing a slew of hip-hop stars. It’s the city of broad shoulders, sure, but when it came to respect for its rap scene, this one had a major chip on theirs. Then, circa 2002, a loudmouthed, hyperactive, one-man street team arrived on the scene, began self-proselytizing about his mad skills to anyone who’d listen, and things changed overnight.
Kanye West, the lower-middle-class, artsy son of an educator, exploded on the scene with The College Dropout, a bold, brash and self-deprecating debut album, and suddenly Chicago had a star to call its own. In those early days, as then-Chicago Sun-Times critic (and early Kanye interviewer) Jim Derogatis notes, West “was Chicago’s own. He’s rapping about working at The Gap at the Evergreen Park mall, and how he barely made enough money an hour to make bus fare. He’s rapping about Chicago.”
In the decade-plus since, however, as West’s star has risen to meteoric heights, and he’s subsequently established himself as one of hip-hop’s most innovative superstars, his connection to his native city has become less palpable. He decamped for Los Angeles, married a Kardashian and began working on a fashion line. Some of those Billboard spoke with are quick to believe West will always be a Chicagoan at heart, but as local rapper Tink, who grew up idolizing West, offers, for someone like her, his trajectory has left him alienated from the city he once called home. “Once you leave the city and you gain so much success,” she says, “sometimes you don’t really understand how the people living in that shit feel.”