Chicago Hip-Hop Before "The College Dropout"

A look back at the Windy City rap scene before hurricane Ye blew through.

There's no shortage of writing devoted to enumerating the ways Kanye West and The College Dropout changed hip-hop. From its sonic palette to its presentation, from 'Ye's creativity to the way he redefined the rapper's role—broadening its appeal as a form of expression for an entirely new audience, freeing artists to explore hip-hop in new ways—it's no exaggeration to say that after Kanye West nothing was the same. Sometimes, it can begin to seem like hyperbole; after all, his impact on beat making predates his debut album, and it's not like De La Soul didn't complicate the frame a decade and a half earlier. But it's pretty well accepted at this point that whether he was pushing hip-hop in a new direction, or just had a finger on the zeitgeist—or both—'Ye was in tune with the way things were and the way things were moving.

But the truth is always more complicated than the conventional wisdom. By zooming in on an artist and tearing down hyperbolic myths about our heroes, we may risk demolishing their reputations. But by hewing closer to truth we can also bolster them, hacking away at the legend, only to uncover a much stronger core, more resistant to the whims of memory and history.

For all that we do know about Kanye West—and we know a lot—his real context as a rapper, the scene he emerged from in Chicago in the late 1990s and early 2000s, is conspicuously obscure. After all, only Kanye (and slightly later, Lupe) became national brand names, stars in their own right who have sustained multiple-album careers. But Kanye wasn't coming out of nowhere. Nowadays, we take it for granted that we "know" Chicago's diverse, burgeoning hip-hop scene. Even if the press hadn't been paying so much attention to the city, YouTube and social media have made it so even foreigners can know (or think they know) the particulars of Chicago turf wars and the music that serves as their soundtrack. In 2014, the light is always shining; you just have to make sure someone is looking.

This was decidedly not the case when Kanye began his long and arduous journey to the release of his debut album. "The bar was so high," says Boogz, a producer who's perhaps best known for creating the beat to Kanye's "New God Flow," but who has also worked with almost every major talent Chicago produced in the early 2000s. He was a founding member of Lupe's 1st and 15th label when he was signed to Arista, was instrumental in producing for Bump J, worked with the LEP Bogus boys, and used to hang at Kanye's house making beats. Boogz has a wealth of stories, and tends to punctuate them with directions about whether or not an anecdote should be printed. "The bar in hip-hop period was Jay Z, Nas, Eminem...even Ludacris at the time, old Luda. It was heavy!"

Mikkey Halsted, at the time, was optimistic. Mikkey, too, came up with Kanye; he was going to be 'Ye's artist, until he signed on with Cash Money during a flush period for the music industry's interest in Chicago talent. (Boogz calls Mikkey "our fucking Jay Z.") Mikkey's biggest song around this time was "Foolish Game," a feature for him off Kanye West's "Go-Getters" group project, a popular tape in the city.

Says Mikkey: "The scene was bubbling. It was like the new generation, almost. It was similar to what's going on now. Hip-hop in Chicago was really looked at like, 'finally, a way that you could make it out the 'hood.' Finally, it was viable. It was a bunch of new South Side guys who were young, hungry, super-talented, and trying to make ourselves the next wave of Jay Z's, Biggies, Nas's—that era that influenced us."

The list of artists who began to pop off at that time reads like an alternate history of what could have been—or maybe what was, just not on a national level. Shawnna, of "Gettin' Some" fame, was a member of a duo called Infamous Syndicate with another rapper named Teefa; they were one of the first signed in the new generation, releasing Changing the Game on Relativity in 1999. Then came Cap.One (yes, 2 Chainz's homie) who signed to Motown and released Through the Eyes of a Don the year after. 

Rhymefest's name was buzzing after he beat Eminem in a national freestyle battle. Other artists—Mikkey Halsted himself, Twone Gabz, Lupe Fiasco, LEP Bogus Boys, Bump J and Sly Polaroid, Young Berg—were on the rise. "The epicenter" of this new Chicago movement at the time, contends Mikkey, was Kanye's house. Or more accurately, Kanye's mom's house, where some of these artists would gather to record. No I.D. served as a kind of godfather to the scene, Kanye West's mentor and and industry connection for artists who saw "getting on" as a narrow sliver of possibility.

Whatever Mikkey's optimism at the time, it was counterbalanced with the narrowness of the opportunities. "The majors—even if they signed you—they wouldn't deal with you, or put you out, or put any money behind you, until you reached a certain number of radio spins. They'd be like, 'You've got to get 350 spins before you even get a video.' Back then, a video wasn't like video now. Video was a minimum $20,000 undertaking! You couldn't just grab a camera and put something out. There was no YouTube. In hip-hop, you were on if you got on BET. And that was really it."

Kanye, of course, ended up paying out of pocket to get "Through the Wire" made. And even then, the video had to be edited by a friend at MTV using his company's editing gear. But it was enough to get him on BET, where history was made.

From a production standpoint, the sound of that era was considerably different than it is today. Mikkey described rappers wanting to sound like Jay, Nas, and Eminem; as a beatmaker, Boogz cites Dr. Dre, Timbaland, DJ Premier, No I.D., and the Hitmen as influences. While backpackers derided Puffy and the Hitmen for their commercial sound, that was the sonic blueprint Kanye, Boogz, Brian "All Day" Miller, and the rest of No I.D.'s circle were most interested in. "It's evident in some of the first beats you hear from Kanye," said Boogz. "Like Jermaine Dupri's album and the Harlem World album with Ma$e. We were 'hit men.' That's why we were using triangles and flex tones and shakers every-fucking-where. That was the Hitmen sound."

Beatmakers from that era in Chicago aspired to compete with the most popular hip-hop then hitting the pop charts (although as a true hometown partisan, Boogz sees Chicagoans as innovators in this arena, implying that Traxster's "Adrenaline Rush" anticipated trap music, and that Timbaland's style came from Wildstyle of Crucial Conflict, "a whole 'nother ballgame we don't want to get into right now"). But Kanye West's sound on College Dropout, like many of his records around that time, marked a shift in a new direction. Boogz argues that was a case of necessity being the mother of invention.

"We sat up all night doing the soul records. Before then, the only person that kept the words [from the samples] in [the beat] was The RZA. Everybody else chopped around them. We didn't have the luxury of money. So the most musical part of the records that we wanted to use? We just kept the fucking words in there. Because if we tried to chop around it, we'd lose the bassline. So a lot of that sound—because I was definitely right there when he was creating it, and I was definitely a beneficiary, because I went on and sold beats of a similar style myself—was made due to a lack of resources."

They made Hitmen beats without Hitmen budgets.

Likewise, recording techniques for Chicago rappers then were very different; it's easy to see the advent of today's adlib-heavy verses in basic recording technology. "We were recording on Roland VS1680s. There was no punching in like that. You had to give it one take! If you fucked up, you're like, 'Hold on. Let me get some water. Lemme sip the drink—OK, let me do it again.' Then your backgrounds, they had to be on point, synched up right. I knew niggas that literally wrote the backgrounds out, like 'Which words am I gonna double?' Whereas nowadays, you just put it in there. If it's off, the engineer lines it up."

As often as Kanye is set up in opposition to the street rap whose dominance he seemed to upset with his success—remember the 2007 sales battle with 50 Cent?—Kanye's context was a little more complex than folks usually give him credit for. To Boogz, 'Ye's rap style was well within the rules of his era. "We were going for au-then-TICITY," he says with extra emphasis. "That was one thing that people from that era of Chicago prided themselves in. We did not lie to you—that you can definitely put in [your article]. We were trying to be the most authentic shit you ever seen. Kanye West is the same fucking person off camera as he is on camera. He doesn't dress differently at the show than he does when he gets in his Lambo."

Chicago was already known in the early 2000s for thoughtful rappers like Common and the West Side bounce sound of rappers like Twista and Do or Die. The early '00s, though, saw the rise of South Side gangster rap, of artists like LEP Bogus Boys—made up of Count, Larro, who was killed in 2006, and Moonie, Boogz's cousin. (Various other rappers would be members throughout the years.) DJs Monty and Mikey of the Ickes projects on the Low End would put out mixtapes of the group, which helped make their names at street level. As with the current wave of Chicago street rap, narratively, authenticity was paramount: "Everything they was speaking about, these lyrics are real accounts of things that have occurred. The music we were going for with them was exactly what I said: let's give it to them in the raw."

It also points to how hip-hop has changed since that time. "If you notice, nobody talks about hustling any more. Because they don't hustle. These kids, they crack cards, they rob, they steal. These guys [in the early 2000s] were selling drugs. Nobody hits the stove any more, you notice. You don't hear Pyrex mentioned any more. Chief Keef and them talk about doing drugs, they don't talk about selling them motherfuckers, though."

Another major story in Chicago prior to The College Dropout's impact was Bump J, who was signed by Lyor Cohen in February 2004—the same month Kanye's debut dropped. "It only took us six months to get Bump's deal," boasts Boogz matter-of-factly. "Six months to get a million dollars." Bump's career was sidelined when he went to jail on bank robbery charges in 2009, but in the lead-up to the release of The College Dropout, his buzz was reaching a fever pitch. Boogz was living with Lupe Fiasco in a house in Riverdale, Illinois, when Bump decided he was going to go solo. "Bump and Lupe would go at each other for hours, rapping. God, if I had a smartphone then. It was dope as hell. One guy just intellectually spitting some dope punchlines. The other guy just putting it right in your face, with the same impact."

Before Kanye dropped his debut, he worked with artists from across the spectrum: from R&B stars like Brandy to street stars like Bump J. But with The College Dropout, his palette was very particular, aiming for a soulful sound that was at odds with what Boogz was used to producing for folks like Bump. "A lot of these raps was so real because the artists had just left the block. And then they come to me, and I got this beat that fits the mood or feeling of how they felt an hour ago. So here comes this rap that's just hot off the presses."

Chicago's sound in that era was largely sample-based; Kanye wasn't unique in that department. But the samples Chicago's producers were using were shaped by their purpose. "When you know you're dealing with street guys, you stop getting into certain records. We started leaning into some rock shit. Like Supertramp and Kansas and Yes. Rick Wakeman, with those airy synthesizers and shit. If we were doing soul, we were looking for a different soul, the harder soul. Angelo Bond, Lou Bond. People that Havoc and them started sampling. Because Mobb Deep had soul, but they had hard soul. Whereas Kanye would take the popular record or the sweet soul record, I would take a record off the same album that had more of a harder edge. Because I didn't give a fuck about melody, like he did. I was all about boom bap."

But although Kanye was using different samples and was far from a street rapper, his identity as a conscious rapper was, much like his sampling technique, a product of need rather than design. "Kanye was never a backpacker," says Boogz. "He was just a fuckin' star." That wasn't to say that he wasn't an enthusiastic collaborator with underground artists. At one point, says Boogz, the Roc was trying to get him to do a Kanye Presents.... album, with his beats, but rappers from the Roc stable. 'Ye wasn't having it. "He started producing for Dilated Peoples, Talib Kweli, Slum Village. He was doing features and records on the underground artists. He was really into the indie scene and the underground hip-hop scene, and they embraced him. He avoided the Nas's and all that. They wasn't letting you on they album! But Slum Village would let you on there. 'You give me the beat, I'll let you on this motherfucker.'"

It was canny strategizing like this that led to The College Dropout and its seismic impact on the industry. Many of the Chicago artists, though, would never have more than a few moments—Shawnna had a massive single with "Gettin' Some," and a couple major label albums. Yung Berg had a pop smash with "Sexy Can I," and has made his fair share of money working behind the boards, and in the boardrooms. No I.D. would become a Def Jam exec even as he continued his work as a respected, high-profile producer. 

For his part, Mikkey ended up one of the most influential artists in hip-hop, even if it was behind the scenes. Lil Wayne has credited Mikkey with helping him transition to a truly national solo star. Today, Mikkey is attempting similar magic with Chicago drill rapper Lil Herb, whom he's taken under his wing. But nonetheless, in his quest to be the next Jay Z or Nas, he argues that he never got his chance. "None of the artists besides one really 'made it,' and catapulted himself to the mainstream. We felt it was a shame. We had all of this talent, but we didn't really have the radio support or the infrastructure to do everything we needed to do to facilitate our own movement. We needed cosigns that were outside of Chicago, label support that was outside of Chicago. In that time, it was largely based on how many spins you could get. With only two radio stations in our market, and with the Midwest being so disjointed, it was really hard to reach those numbers that the South was reaching."

Boogz, though sees that generation's impact as a victory. "All of us had some sort of hand in The College Dropout. Credited or non-credited. If you look at Kanye's tweets of the last three days, he was like, "shout out to everybody who was there to help it and contributed even the smallest amount to it." So The College Dropout was like our album. We are all products of Kanye's house."

"You notice everybody that comes from there. We all made it in the industry some sort of way. We entered. Kanye of course went on to make a lot of money. I made a lot money! Shawnna, Mikkey, Rhymefest, myself, we all got in, because we were all pulling each other up. And at the head of all this shit was fucking Kanye. He was our boss because he was fucking great."

Boogz, true to form, also directs a fitting closing image for this article. 

"Kanye was the only person that I knew was gonna be star when I first met him. I knew it. Just like Yung Berg. I knew Yung Berg was gonna be a star when I met him too. He's had some character flaws, but he's still got the 'it' factor. But we were all nominated for a Grammy—this is some shit to end the piece with. At the Grammys, two weeks ago. Me, Kanye, Yung Berg, King Louie, Chief Keef, Malik Yusef, Lupe Fiasco, The Internz. That's a lot of fuckin' people from one town, right? It was like 11 fucking people from Chicago that was up for a Grammy. And none of us fucking won," he laughs. "Except No I.D."

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