Raymond O’Neal doesn’t remember where he was the first time he heard the 1989 Boogie Down Productions single “Why Is That?” But he remembers who played it for him: Michael “Mic” Shane. “If it weren’t for that very moment, I’m pretty sure the trajectory of my life would just be completely different,” says O’Neal. By 1995, O’Neal had become an executive vice president at Vibe magazine publisher Vibe Ventures, a job he owed in part to his collaborations with Shane. In the early 1990s, they’d worked together in the Chicago rap scene to organize shows, manage local acts, and launch the city’s first hip-hop magazine, FlyPaper.

Shane couldn’t always directly employ his friends, but he consistently championed anyone trying to build a Chicago hip-hop scene that could rival anything on the coasts. Bobby Sox, a visual artist and tattooist who ran Wicker Park hip-hop lifestyle boutique Triple XXX, recalls how doggedly Shane would press him and their mutual friends to pursue their dreams. “We’d talk about what we’d do, talk about pushing this hip-hop thing—Mic didn’t take no for an answer,” Sox says. “When you say ‘a driving force,’ that’s what that dude was—especially about the culture. He inspired all of us.”

Shane showed O’Neal a vibrant community in their chosen hometown, but neither of them saw that scene reflected in national hip-hop media, at the time epitomized by The Source. “Chicago doesn’t have a voice in this game between the coasts—that’s when we determined, ‘Fuck it, let’s do our own thing,’” O’Neal says. In 1991, they partnered with BboyB of graffiti collective the Artistic Bombing Crew to launch their magazine, originally titled The Rap Sheet. After they received a cease-and-desist letter from another magazine with the same name, they switched to FlyPaper.

  • This 1990s Media Burn Archive clip includes Wicker Park footage showing Triple XXX and Lit-X (also known as Literary Xplosion).

In the early 90s, as Chicago hip-hop grew big enough to get out of house music’s shadow, Wicker Park became the scene’s north-side home. Sox’s Triple XXX shop and Afrocentric bookstore Lit-X were right at the six-corner intersection near the Damen Blue Line station, and just north on Damen was Beat Parlor, a hip-hop-heavy record store run by former Medusa’s doorman Howard Bailey. The nightclub Red Dog, on the northeast corner of North and Damen, became a beachhead for hip-hop nightlife in the neighborhood. Wicks began throwing shows regularly at the club in early 1993, and the FlyPaper team distributed the magazine there. A bit south on Milwaukee was the Copy Max where BboyB used to design FlyPaper.

Those connections came in handy as Shane and O’Neal began to work in a more hands-on way with local rappers. “We literally had our pick of the greatest MCs in Chicago, in terms of managing,” O’Neal says. Among the artists they managed were Gravity (a member of the Elements of Nature collective, aka EONs) and the duo Kinetic Order, aka Rob Bradford (“Rob Free”) and Julian Akins (“Judgmental”).

Shane moved back to Chicago at the beginning of the 2010s, when Johnson was planning to launch Know 1 Radio. She reached out to Shane to work for the station, which began broadcasting in 2013, and he eventually became its chief operating officer. “He produced all the young people,” Johnson says. “He taught them about radio, taught them about hip-hop. He taught them about logistics.”