RedEye spent the day with Lil Bibby from Chicago's East Side. Here's what he had to say about himself and the city.

In May, Chicago rappers comprised a whopping 40 percent of XXL Magazine’s “Freshmen” list, an annual spotlight of 10 names to watch in rap that previously has included names like Lupe Fiasco, Kid Cudi and Kendrick Lamar before they were huge. No one was surprised to see Lolla 2014 acts Chance the Rapper and Vic Mensa on there. Same with Def Jam-signed Lil Durk.

Not as predictable was the slot for lesser-known East Side native Lil Bibby, whose sophomore mixtape, “Free Crack 2,” arrived Friday. It represents an impressive maturation of his sound, departing from a tendency to invoke cliched discussions of making money and distrusting women in favor of deeper lyricism and production that pushes Bibby out of his stylistic comfort zone. Not to mention credibility-boosting star power: In addition to production from Bangladesh (Lil Wayne’s “A Milli”), the tape features Wiz Khalifa, T.I., Juicy J, Jadakiss and Bibby’s frequent collaborator and longtime friend Lil Herb, who has had a huge year himself—guesting on Common’s new album and Nicki Minaj’s “Chi-raq.” Bibby too recently has appeared with Minaj (on Juicy J’s “Low”) and earned big-time fans like Drake and Kevin Durant.

With Bibby (whose real name is Brandon Dickerson) achieving that kind of success at just 20 years old, no one would blame the rapper for kicking back and toasting his accomplishments. Yet anyone who listens to 2013’s “Free Crack” or, in particular, its massively improved sequel will understand why Bibby doesn’t relax. Still residing in the East Side’s South Shore neighborhood, he comes from a 2-block by 4-block section that has seen three mass shootings since February of 2012, leading residents and even police to dub the area “Terror Town.” He’s soft-spoken and somewhat shy during an interview at the RedEye offices, but when asked about life in his neighborhood, his demeanor changes. He focuses, and his voice strengthens, albeit with more than a hint of sadness.

“It’s crazy as hell,” he says of South Shore’s troubles, like the June shooting in which a gunman fired on a crowd at a strip mall, wounding six. “I don’t know what to do about it. I just did a little back-to-school thing and gave away backpacks and supplies for the kids. I’m trying to think of a way to do more, but it’s hard, man. People are one-track minded. All they want to do is stay in the same zone. There’s no way out of it if you’re gangbanging. It’s either death, you’re in [prison] or you grow up to be an old drunk or something. It’s a repeated cycle.”

Part of the music industry attention for Bibby comes from his ability to deliver frank and brutal narratives about street life, lazily identified as “drill music”—a term broadly used to describe the work of several Chicago rappers that have emerged since 2012’s Chief Keef-led rap boom that brought major labels flocking to town. Songs like “Free Crack” and standouts “Water” and “That’s How We Move” might be dismissed as standard gangster rap in other hands. In Bibby’s, they carry an extra level of grit.

And while he’s hardly the first rapper to chronicle this subject matter on record, that doesn’t take any urgency out of new songs like “Dead or in Prison,” on which Bibby rhymes about the paranoia that comes with newfound fame. “They see a young n***a stuntin’/Now they want you killed/Gotta watch out for the young’uns/Tryin’ to pay their bills.” On the same song, he references the next generation: “This [bleep’s] for my young n***as/In the hood, with no fathers/[bleep] you see in these streets/Should encourage you, to go harder.”

“That stuff I rap about is real,” he says. “My neighborhood has so many enemies that something might happen while you’re heading to the job or getting back. People need to know what’s going on because they don’t care otherwise. I don’t speak positive on this stuff; my raps aren’t glorification. They’re advice.”

Of course, Bibby doesn’t know the future of the streets that created him. But he’s optimistic that they won’t define who he is.

“People recognize me now. I’m doing shows in, like, Rhode Island and Iowa,” he says with a laugh. “When I was coming up, we saw what Keef, Lil Durk and Lil Reese were doing. I knew I could do it. I’m going to try to start reaching out to other guys in the rap scene here. Maybe I can help them see about the bigger picture.

“You gotta go outside and look around. It’s good for you.”