On Wednesday, November 13, DaWreck of west-side hip-hop group Triple Darkness posted a mini documentary to YouTube about E.C. Illa’s 1994 EP, Live From the Ill. The video E.C. Illa Dissecting Live From the Ill shows E.C. sitting in front of a camera and talking for almost 28 minutes about the creation and history of his EP. When he dropped Live From the Ill, E.C. was one of Chicago hip-hop’s brightest stars, and his recollections of the music, people, and places that filtered into the EP make the video a must-watch for any hip-hop head. The release of the documentary was timed to promote a 25th-anniversary CD reissue of Live From the Ill by Big Herc Collections that came out the same day, but it stands on its own as a crash course in local rap history.
Prior to Live From the Ill, E.C. had largely recorded in the secondary studio at Chicago Trax, where he learned the craft by watching artists in the main studio, including Ministry front man Al Jourgensen. While E.C. was at Chicago Trax making the Live From the Ill cut “Funky Like This 94,” Common was hanging out in the studio—and E.C. says he dug the song so much he wrote a verse for it on the spot, only deciding at the last minute not to record it. E.C. took a recommendation from his friend the Legendary Traxster and made much of the EP with house engineer Dane Roewade, who’d worked on the single “Doomsday” for D 2 tha S, Traxster’s duo with rapper Kay-Tone. E.C. also recruited Kay-Tone (uncle of future Chicago hip-hop star G Herbo) to deliver the hook on the nimble, funky “It Don’t Stop.” “Kay-Tone makes this classic chorus,” E.C. says in the documentary, “that went on to be an important part of Chicago hip-hop history.”
Of course, no consensus exists about what counts as an important part of Chicago hip-hop history. That history has never been compiled, and most attempts to recount it have either been self-consciously niche or depressingly shallow and misinformed. The new podcast Place in Sound, from streaming service TuneIn, unfortunately belongs in the latter category. The same day E.C.’s documentary arrived, TuneIn dropped the first season of Place in Sound, devoted to the music of Chicago (each subsequent season will focus on a different city). TuneIn isn’t new to audio storytelling, and since its launch in 2002 has built an audience of more than 70 million listeners per month. Backed by several venture capital firms, including favorite Silicon Valley funder Sequoia Capital, TuneIn was valued at $500 million at the time of a 2017 deal reported by Bloomberg. But despite all the money it has sloshing around, the company couldn’t be bothered to make Place in Sound more than a collection of regurgitated half-truths and cliches about Chicago music.
The Place in Sound team wanted to spotlight Chicago’s reborn hip-hop scene and demonstrate its connections to the city’s musical history—an admirably ambitious goal, and one I can’t imagine any podcast achieving in a four-episode season totaling 131 minutes. In the final episode, host Anthony Valadez acknowledges that time constraints limited the program’s scope, but what he doesn’t say is that they apparently also prevented its creators from addressing their preconceptions and blind spots.
TuneIn is hardly the first outlet to parachute into town hoping to tell the world about the exciting developments in Chicago hip-hop. But while so many others indulge in an exploitive fascination with drill, Valadez barely mentions it, and then only in terms of its relationship to systemic violence. I’d thought it’d be impossible to talk about Chicago hip-hop in the 2010s and completely leave out Chief Keef, whose astronomical rise in 2012 put the national spotlight on the local scene. But unless I missed a passing reference, Keef is never named. Valadez and Consequence of Sound critic Wren Graves suggest that Chance the Rapper’s 2016 mixtape Coloring Book was “the coming-out party for the Chicago hip-hop movement,” which I suppose could be true if by “movement” you mean “people who appear on Coloring Book.” By my reckoning, they’re four years late: the floodgates really opened for a new wave of Chicago hip-hop in May 2012, when Kanye West shouted out LEP Bogus Boys, King Louie, and Chief Keef on the GOOD Music remix of Keef’s breakout hit, “I Don’t Like.”
Earlier chapters of Chicago’s hip-hop history don’t fare much better in Place in Sound: it trots out cliches about the scene’s supposedly fallow period in the early 90s, ignores the mid- to late-90s popularity of west-side chopper rapping, and suggests that ghetto house is a subgenre of rap, not of house music. The podcast’s version of house’s history is equally suspect, but if I keep going, I’ll start to feel like I’m piling on.
Despite its faults, Place in Sound makes a serious effort to enhance its audience’s appreciation of current Chicago hip-hop by digging into the past. But there are more rewarding ways to do that digging—especially since it’s been getting a little easier to hear old and unjustly obscure local hip-hop that’s fallen out of print or never got properly released in the first place.
Reissues have never gone out of style, but since vinyl reemerged as a popular format, the proportion of reissues designed to appeal to serious collectors has jumped. This growing market has made it possible for a clutch of smaller labels to surface some remarkable 80s and 90s Chicago hip-hop, almost all of which I think is crucial to understanding our history.
Some of these reissues have come out in absurdly small editions, either in an attempt to create the appearance of exclusivity or in an acknowledgment that their potential audience is tiny. Big Herc pressed just 94 copies of E.C.’s Live From the Ill, and local microlabel Icy Palms made 54 cassette copies of an unreleased 1989 album called Cause 4 a Riot! by Chicagoland trio Wildstyle. The tapes sold out even before their mid-November release, but the music is streaming on Bandcamp, and Wildstyle rapper Kevin Beacham (who’s also a hip-hop historian) recently published a 30-part series about the group on Medium.
Possibly even rarer is a T-shirt featuring the menacing artwork for M.C Def Ski’s obscure 1993 cassette EP Rap Tyrant. Its cover is a flash photo of an impassive Def Ski standing in a graveyard (though no headstones are visible), wearing sunglasses at night and holding a pickax in one hand and an ax in the other. The shirt came out this summer, and it’s impossible to say how many were printed before the small clothing company responsible apparently vanished from the Internet earlier this month.
In the spirit of the Reader‘s gift guide, I’ve chosen to focus on recent Chicago hip-hop reissues that you can buy on physical media without spending serious cash on the resale market. Even in 2019, it’s still a little anticlimactic to unwrap a download card!
Rubberoom
Gothic Architecture
$20.34 plus shipping for double LP (subject to exchange rate), $8 for download via Bandcamp
When Rubberoom entered United Technique Studio to record their 1995 debut EP, Gothic Architecture, the six-member crew had earned a following by appearing at a weekly freestyle series at Lower Links, but they hadn’t spent much time in a professional studio together. They didn’t have much money to spend either: Kevin “Fanum” Johnson, one of Rubberoom’s three producers, says they’d scraped together enough to cover a single song. But United Technique owner and engineer Rae Nimeh offered to let them record more material for the same price, working quick and dirty with a Sansu six-track tape machine. Johnson describes the quality of the results as “releasable,” and Rubberoom eventually included all ten tracks from the sessions on Gothic Architecture, which they put out on cassette through their own Elastic Recordings.
Some fans weren’t happy about the production quality of Gothic Architecture, but it captures Rubberoom’s hard-hitting, grimy sound and their three MCs’ limber rapping and raw energy. “I didn’t really care about standards,” Johnson says. “We felt so confident in it. We just cared about putting it out and getting it to the people so they can hear it—that’s how confident we felt about our music back then.” The group’s intuition served them well: on the strength of the EP, the Notes From the Underground column in Vibe magazine put the spotlight on Rubberoom in November 1996.
Rubberoom lost their momentum after New York indie 3-2-1 Records folded shortly after releasing the group’s 1999 debut album, Architechnology, and they broke up in 2000. In the years since, Johnson has gotten requests to reissue Rubberoom’s material—in fact, a Gothic Architecture vinyl release would’ve happened already if the person interested had been able to work with the masters Nimeh had given Johnson.
The reissue is happening now because Berlin-based HHV could make do with the material Johnson provided. Spread out over two LPs, it adds three instrumentals to the original track list. HHV designer Boggie Cramb even re-created the original artwork, proportioned for a cassette J-card, to fit a vinyl release. In the course of getting this old material released again, Johnson spent a lot of time with it. “I listened to it as a producer—I’m like, ‘Ooh, I wish I would’ve did that differently,'” he says. “But then at the same time, I’m like, ‘Wow, I felt what I felt in that recording—I felt our passion. I felt our drive to have no fear.'”

Nacrobats
A in the Square and companion book A Love Supreme
$25.99 plus shipping for vinyl (with book while they last), $20 for download via Bandcamp (no book)
When Sterling Price, aka Pugs Atomz, started attending Kenwood Academy in the early 90s, he was a graffiti artist and a budding rapper. He’d hoped to find some teenage hip-hop crews at the school, but as far as he could tell, there was only one. “I felt like a lot of people my age really didn’t have a support system in the sense of getting into hip-hop,” Pugs says. “Everyone was way older, but also they’re off chasing their dreams.” So in 1993, he launched the Nacrobats crew.
“We just all were learning together,” he says. “One person will figure out how to do wholesale, and then they passed that on. One person will figure out how to do websites, and they passed that on. One person figured out how to book shows out of state, and they will pass it on. It’s definitely a network—I really didn’t know how big it would get.”
The crew peaked at around 200 members, many with overlapping affiliations—Alley Katz Crew, for instance, topped out at 50 people (one of whom was famed artist Hebru Brantley), and most of them were also in Nacrobats. Their ranks ran so deep that even today you can find former members everywhere you look. Future rap heroes Offwhyte, Psalm One, and Open Mike Eagle were all involved with the crew in their youth. Brian Nevado, part owner of crucial Loop streetwear shop Jugrnaut, rapped in a group called Lyric District that formed after a Nacrobats meeting at a Burger King near Congress and State. Andre Vasquez, sworn in as 40th Ward alderman in May, used to be a battle rapper who called himself Optimus Prime, and he joined the Nacrobats after entering one of their freestyle cyphers outside that same Burger King.
Pugs started recording in 1996, and other Nacrobats followed suit, releasing a torrent of homemade mixtapes, professionally dubbed cassettes, CD-Rs, and CDs. Pugs retired the Nacrobats name in 2003, but he’s kept in touch with people in the network he developed. Earlier this year, hyperprolific rapper and former crew member Infinito 2017 reached out to Pugs about releasing a vinyl compilation of old Nacrobats material on his Culture Power45 label. The resulting LP, A in the Square, is accompanied by a 50-page book called A Love Supreme, which collects flyers, photos, and essays from former Nacrobats; the package started shipping in mid-November, and Pugs is also using Threadless to sell a new Nacrobats T-shirt he designed.
As part of compiling A in the Square, Pugs reached out to crew members to make sure they wouldn’t be embarrassed by their old material coming back to light. “Some people’s rap styles have changed,” he says. “Oftentimes artists look back and are like, ‘Ooh.'” The process has given Pugs a greater appreciation for what he and his friends accomplished with Nacrobats. “In the 90s, there was a movement happening—it was definitely a movement in art, a movement in culture, a movement in music,” he says. “It was all happening ’cause we were all feeding off this thing. None of us really could even see it.”

Various artists
Closed Sessions Vol. 1
$20 plus shipping for vinyl, $7 for download via Bandcamp
Chicago hip-hop label Closed Sessions emerged in 2009, arising from crucial Chicago hip-hop blog Ruby Hornet, and its creation illustrated one of the best things about the blog era: the blurring of boundaries between covering an artist and releasing their music allowed publishers to make dazzling creative leaps. Closed Sessions cofounder Alex Fruchter (aka DJ RTC) was also editing Ruby Hornet, which brought together fans and creators of underground hip-hop. “That was almost like the wild, wild west,” Fruchter says. “Blogs were filled with passionate kids figuring out the Internet, making their own connections with artists. Operating an alternative, curated distribution network for—mainly, definitely at the start—independent artists. What happened, not just in Chicago but in other cities, the blogs, a lot of the good ones, transformed.”
Ruby Hornet threw parties at Lava Lounge with local and touring rappers, and Closed Sessions evolved from the Ruby Hornet crew’s habit of taking visiting artists to Soundscape, a Humboldt Park recording studio owned by future Closed Sessions cofounder Michael Kolar. Fruchter and company would invite the MCs to record, and Fruchter, always given to documenting, filmed the sessions. After inviting cult rapper Curren$y to rap over a Tony Baines beat in July 2009, Fruchter and his team gathered a mess of MCs to record one-offs and collaborations with almost as many different local producers. In March 2010, Fruchter announced the resulting compilation, Closed Sessions Vol. 1, on the Ruby Hornet site and posted a link to download it for free.
Nationally famous out-of-towners such as Bun B and Skyzoo raised the profile of Closed Sessions Vol. 1 when it came out, but the Chicagoans define it and the era it represents. The songs combined artists from different cliques, from far-flung neighborhoods, and from distinct waves of Chicago hip-hop that barely overlapped. “Fresh Academy,” for example, features blog-era upstarts Kidz in the Hall alongside Mikkey Halsted, who by then was a long-grinding veteran. It’s hard to imagine such a collaboration existing without blogs such as Ruby Hornet and Fake Shore Drive putting up tents big enough for so many different parts of the local scene.
“You had two distribution centers run by two people with different music tastes, different connections within the scene. And artists could now see what each other were doing, and you could all be online in the same place,” Fruchter says. “If you’re from Hyde Park and that hip-hop scene, you could see what the people on the north side were doing, and you could appreciate it without leaving your house, without feeling threatened, and could start to collaborate.”
Closed Sessions Vol. 1 wasn’t available in a physical format till this April. “Having it on vinyl was something that we toyed with, and maybe desired, since the inception,” Fruchter says. “But when we started the project, that was just an unattainable thing.” The remastered LP version is on mustard-yellow vinyl, and 2012’s Closed Sessions Vol. 2, reissued digitally on November 12, will eventually have a relish-green vinyl edition. Closed Sessions also partnered with Dark Matter this month on a tenth-anniversary coffee blend packaged with two white-label seven-inches of Closed Sessions material, but it’s sold out.
The arrival of the Vol. 1 vinyl prompted Fruchter to consider his history. “I remember getting the vinyl for the first time and just thinking, like, ‘Wow, this started as an idea, a hope, a SendSpace file,'” he says. “Ten years later, we have a label, we have a history, we’re part of the stories and lives of so many different people and great music.” v