How Chicago rap became a home for controversial, visionary stars

As it celebrates its 50th birthday, we are mapping hip-hop's story on a local level, with more than a dozen city-specific histories of the music and culture. Click here to see the entire list.

A city for poets, brawlers and hustlers — that's how the writer Nelson Algren described his chosen hometown in his book Chicago: City on the Make. That was in 1951, the prime of the Maxwell Street blues. But I've always thought it also applied to the city's most emblematic rappers, especially so in the past two decades, as a few iconoclasts — chroniclers and products of corruption — transcended the Midwest's status as hip-hop flyover territory and elbowed their way into greatness. Almost as a rule, that greatness has been complicated: by a chip on the shoulder, a misunderstanding, sometimes by the city itself. But that suits the place: "For always our villains have hearts of gold," wrote Algren, "and all our heroes are slightly tainted."

That the third largest American city, which urbanized the blues and invented house, was considered a backwater for the first 25 years of hip-hop's history is hard to fathom now. But in the '90s, while the genre became a juggernaut on the coasts and down South, Chicago was an afterthought. When a 19-year old rapper named Common Sense appeared in The Source's "Unsigned Hype" column circa '91, it was with a backhanded compliment: "Impressive rhyme skills especially for an MC coming out of Chicago," as if it were a shock they sold microphones there. Common's artistic identity was defined against the gangster mainstream — an intellectual in a newsie cap, pining for the days when rap had soul. He had it in spades thanks to No I.D., a fellow South Sider whose lived-in beats would be the keystone of a new Chicago sound.

The year I was old enough to drive on Lake Shore, the biggest song in my high school — and for one week, the entire country — was "Slow Jamz" by Twista, which featured Jamie Foxx and a new guy, Kanye West. (New to me, at least.) "Slow Jamz" was goofy but sort of genius — the helium Luther Vandross sample, the "state of R&B" meta-commentary, the lines that made you cackle at their knuckleheaded audacity. I knew Twista, the Guinness-certified fastest rapper alive, from the radio, where they'd sometimes play his song "Po Pimp" with the West Side group Do or Die; that was about as big as it got where local rap was concerned. "Slow Jamz" marked the first time a Chicago rapper had scored a Billboard No. 1, and there's justice in that milestone going to Twista, the unsung hometown hero, even if the song was pure Kanye.

The same month "Slow Jamz" topped the charts, I downloaded The College Dropout on LimeWire, my pirating platform of choice; the files were mislabeled "KAYNE WEST." People who once worshipped Kanye have relitigated their relationship with the rapper in recent years, but it's hard to overstate how it felt back then, listening to a Chicago rap album we all knew was an all-timer. We knew the backstory, too: A nerdy beat-maker rises through the ranks of the premier NYC street-rap label, leaps atop boardroom tables to convince powers-that-be of his solo promise, shatters his jaw in a rented Lexus. In the era of 50 Cent and The Game, this was a middle-class Midwestern guy whose ambition so happened to be insane, who'd be dreaming one minute of walking out on his retail job and the next of bringing Jesus to the club as his plus-one. And all of it sounded so good: Beyond the chipmunk soul sample work (a No I.D. trick Kanye had improved upon), there were scores of live strings and congas and choirs that blew way past the budget.

By 2013, that nerdy Chicago beat-maker, now 36, had amassed 21 Grammys and five multi-platinum solo albums (plus another with Jay-Z), the most recent of which critics had called a generational masterpiece. He'd mainstreamed Daft Punk and sad Auto-Tune rap, pissed off two presidents and at least one pop princess, and become the most acclaimed and controversial rapper of the century so far — and he was frustrated. "I'm assuming I have the most Grammys of anyone my age, but I haven't won one against a white person," he told The New York Times that year. He'd found rap's ceiling in the minds of the old gatekeepers, and with his sixth album he'd take what goodwill those gatekeepers had left for him and shove it. Yeezus juxtaposed civil rights iconography with bad puns and degrading orgies and made it all sound like a Nine Inch Nails nightmare. On Dropout, West had checked his own ego with humor and pathos; now he countered his god complex with chemicals and a death wish. It was anti-pop, anti-celebrity, anti-commerce, or so we believed. Yet it predicted how aesthetics could be mistaken for politics, and how rap would look and sound for the next 10 years: surly, medicated, ostensibly punk.

It was also the most Chicago album that Kanye had ever made. From its full-body bass and buzzsaw synths, you could tell he'd been studying acid house. As for drill, the heavy new sound of the city, Chief Keef's placement on the hook of "Hold My Liquor" told you what you already knew if you'd heard West's remix of the teenage rapper's "I Don't Like" the year before. Keef had been a favorite in the local public schools; when an early 2012 viral video brought the 16-year-old to the public eye, it hit hip-hop like a bomb. Suddenly, all anyone industry-adjacent could talk about was drill, the slow, menacing local trap offshoot which had been bubbling up for years, just out of the media's view. (Had your concept of Chicago rap come from magazines and blogs, you'd have thought it consisted only of hipsters.) Drill was unforgiving music with a dark code of honor, but the anthemic hooks, catchy ad-libs and wall-of-sound beats courtesy of Young Chop were, in their own way, euphoric. Keef was drill music's poster child, but the scene went remarkably deep — spend a couple hours on YouTube and you'd find dozens of kids who spoke the same lingo, warbled similar dirges just out of pocket, and seemed just as detached about anything the future might hold.

Was drill the most compelling regional rap movement of the early '10s or the self-fulfilling soundtrack of the city's worst ills? Ask any Chicagoan back then and you'd get an earful, though often missing from the conversation was anything to do with Keef (or Lil Durk, or Katie Got Bandz) as an artist, not a cipher for gun violence or a passive product of his environment. "Chief Keef scares me," said Lupe Fiasco — Chicago's first post-Kanye rap star, who'd brought a certain cool to thinking man's rap in the mid-'00s — in 2012 . "Not him specifically, but just the culture he represents." By then the ink was dry on the year's buzziest record deal: Interscope had signed Keef for upwards of $6 million, though the relationship would be short-lived. When his debut album, Finally Rich, moved just 50,000 first-week physical copies, the industry frenzy cooled off immediately. If anything, Keef had become a liability.

What looked like failure within the establishment was, as it turned out, a paradigm shift. Keef's star had risen in the twilight of the transition period between CD sales and DSPs. He was the first in a new generation of hip-hop stars for whom the old system was incidental; he'd become known without a label, a co-sign, a press run. He'd also invented a language of sorts — an intuitive way of rapping and song-making that almost obscures itself, swinging to its own rhythm and burying meaning in atmosphere. There has been no greater influence on how rap sounds, and how we find it, in the decade since Keef surfaced. SoundCloud brats (Trippie Redd, Lil Pump), traumatized anti-heroes (NBA YoungBoy, 21 Savage), bleeding-edge stylists (Lil Uzi Vert, Playboi Carti), lean-soaked balladeers (the late Lil Peep and fellow Chicagoan Juice WRLD), significant artists in their own right, all are in Keef's formal debt. (Even wilder: they're proud to admit it.) And when the industry jumped ship on drill after Finally Rich, the culture carried on a life of its own, mutating as it spread to Brooklyn, London and beyond, where its varied sounds remain potent and its artists are similarly moralized.

As A&Rs went panning for more Keefs in the Chicago rap gold rush of 2012, what turned up instead was a full-fledged hip-hop ecosystem, spilling over with talent. Within drill itself was a world of diversity, from wise-cracking elders like King Louie to serious writers like G Herbo. Alongside it were Chance the Rapper, Vic Mensa and Noname, artists raised in the spoken-word poetry circuit who performed with full bands. There were femme fatales like Sasha Go Hard and Shady who spit as hard, if not harder, than the Glory Boyz, and leagues of producers (DJ Kenn, DJ L) whose battle-cry beats would inspire countless more. Out came sui generis acts like Tree, the raspy soul-trapper; Cupcakke, the bugged-out provocateur; Sicko Mobb, the duo who practically predicted hyperpop. (I could go on all day.) "Where had all these rappers been?" the hip-hop world asked, and Chicago answered: "Right here. Where were you?"

Where to start with Chicago rap:

• Do or Die, "Higher" (Remix) ft. Kanye West & Shawnna (2005)
• The Cool Kids, "Black Mags" (2008)
• Shady, "Go In" (2011)
• King Louie, "Bars" (2012)
• Katie Got Bandz, "Ridin Round and We Drillin'" (2012)
• DJ Nate, "Gucci Goggles" (2012)
• Lil Durk, "L's Anthem" (2012)
• Tree, "Probably Nu It" (2014)
• Chief Keef, "Earned It" (2015)
• Valee, "Shell" (2018)

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