Billboard Women in Music 2025
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.
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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.”
What, then, is Chicago to make of West’s most recent flare-up? He’s their native son, sure, but does that make them more apt to defend a man who recently declared slavery “a choice” and openly supported President Trump, even as the man in the Oval Office has threatened to send in “The Feds” to stop the “carnage” in Chicago as if it were a third-world war zone? West has said he’s aiming to unshackle society form the constraints of groupthink, but what about those who’ve supported him from the outset? Do his fellow South Side natives see his recent behavior, his talk of “free thought,” as impacting his legacy as it relates to their city?
“Now in Chicago, we got tough love for Kanye,” says Tink. “We gonna always love Kanye because he did a lot for this city and put a spotlight on us, but there’s deeper issues that we wish Kanye would touch on.” Those include the city’s violence, the poverty, the fact that Chicago remains one of the most segregated cities in the country. “It hurts our feelings when he doesn’t understand where we coming from,” she adds. “He’s from the same ground we walked on. When you still living in the city, you understand the violence and how it affects your family… we’re actually living it. We looking at our siblings and our cousins dying. It’s real for us. For Kanye, there’s a clear disconnect.”
This feeling was only exacerbated when West’s longtime friend and fellow Chicago native Che “Rhymefest” Smith criticized the rapper last week for allegedly abandoning Donda’s House, a nonprofit co-founded by the two Chicago rappers in honor of West’s late mother. Additionally, on Friday, Donda’s House released a statement claiming that many supporters of the organization have turned their back on them in the wake of West’s pro-Trump comments. To make matters worse, the rapper has allegedly not responded to multiple attempts by the organization to secure funding for ongoing projects.
@Drake when G.O.O.D. Music sends the money they owe you, will you please help us rebuild Kanye’s mothers house for the youth of Chicago. I spoke to Kanye about it. His response was “fuck the youth of Chicago”
— Rhymefest (@RHYMEFEST) May 26, 2018
“As we seek support to convert Kanye’s childhood home into a recording studio museum and learning space, we have been unable to secure the financial support of Kanye despite multiple attempts, and despite those early conversations about his plan of support and advocacy for the youth in our programs,” the statement reads.
The following day, West’s wife, Kim Kardashian West, took to Twitter to defend her husband and launched personal digs at Rhymefest. In the end, Donda’s House issued a statement that in light of Kardashian West’s comments and the controversy surrounding her husband, they would no longer be using the name “Donda’s House” for the organization.
DJ Nehpets of Chicago hip-hop station Power 92.3 doesn’t defend West’s recent behavior, but like Tink, he believes it’s a symptom of the privileged life to which he’s long become accustomed. “When you grow to that level of stardom and celebrity, you can’t relate to [the average people] anymore,” Nehpets says. “Kanye can’t talk about the same struggles we going through. He can relive them, sure. He can talk about the struggle of eating ramen noodles, but we know he ain’t really eating them anymore. And then it comes off as inauthentic.”
Derogatis echoes Tink’s “tough love” sentiment but says he believes Chicagoans, if only because of self-indulgent pride, are more likely to give West a pass no matter his sometimes absurd actions. “There’s still a certain pride here for him,” Derogatis says. He draws an intriguing comparison between how Chicagoans feel when West runs his mouth and how a Liverpudlian may have felt when their native son John Lennon was staging sit-ins and declaring The Beatles were “bigger than Jesus.”
“When Lennon was shooting his mouth off and being a jerk, I’m sure the people in the pubs in Liverpool were saying, ‘Oh, that’s John! But he’s our boy. He’s doing incredible things!” That’s sort of the attitude in Chicago [with West],” he says. “It’s like, ‘If Kanye would only just shut up…’“
Though, the consensus among those Billboard spoke with is that unlike, say, Chance the Rapper or Common — who have are more constant presences in the city — Kanye has never been as pointed in his affection for Chicago. “I don’t think he has the strong connection with the Chicago community anymore that, say, Chance has,” Derogatis admits. “Chance is raising money for schools here, he’s very active. Common’s Hollywood, but he’s back here all the time and he’s doing stuff for the community all the time. And Kanye, well, he’s going to runway shows around the world.”
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But the fact that West continues to make some of the most daring, provocative and groundbreaking hip-hop music only further serves to complicate the city’s relationship to him, says Alex Fruchter, who runs local hip-hop label Closed Sessions and teaches music marketing at Columbia College Chicago. Interacting on a near-daily basis with young artists and music students, Fruchter says West is constantly cited as a major creative influence and point of pride for young Chicagoans.
“He’s going to always be in that influential conversation for people that make hip-hop music for years and years to come,” Fruchter says. “His impact might not have been on the grassroots level lately, but it’s on a higher level here because he’s from here, and has played such a big role in Chicago hip-hop.”
“I think the tragedy of Kanye’s career is he is a genius,” adds Derogatis, and his sometimes-outlandish behavior threatens to overshadow his art. “There’s no two ways about it. I will wrestle any critic to the ground who wants to argue otherwise. The concept, the production, pushing the envelope of what can be done in hip-hop; it’s the whole package.” Ultimately, though, Derogatis contends, West’s creative contribution to music is why he believes Chicagoans are willing to play the long game with the rapper. “We’re more willing to give him a break, because in the end, what people are going to remember in 10-20 years is the music the guy created.”