There's an area in the South Shore neighborhood of Chicago known as Terror Town. It’s a 2-block-by-4-block area that has seen no less than three large-scale shootings in the last 3 years. This is where the rapper Lil Bibby lives, he of the boyish looks and the grown-ass man voice. He debuted nationally in August of 2012 alongside lifelong friend Lil Herb via "Kill Shit," a song that stands out as the absolute hardest song recorded by children I’ve ever heard. Bibby's work is a live play-by-play of chaos, with numerous references to paranoia that comes with simple trips to the store—"This real life, real facts, this ain't rap/ Walk into that corner store, we had to stay strapped/ Yeah, most of these niggas can't relate to that," he raps on "EBT to BET."

The moment that gave Bibby his introduction to the world—the initial gold rush of the drill sound, with every rapper with a 773 or 312 area code getting a look and/or a deal—has passed now. His latest tape, Free Crack 3, feels like a game attempt to escape the box that being labeled a "drill" artist puts you in. The tape comes with via a mix of big-name grabs (Future and Metro Boomin on obvious radio ploy "Aww Man") and local legends (Jeremih, R. Kelly, and Common, who drops one of his better verses in awhile on "Speak to ‘Em," all appear). The C-Sick produced "If He Find Out" features a stellar collaboration between Tink and Bibby. As expected, Lil Herb stops by for "Ain't Heard Nuthin Bout You," and the song is such a great example of the chemistry between the two that they’ve been promoting the single as "Kill Shit pt. 2."

As he expands his range of guests, his lyrical ability leveled up significantly. By and large, Bibby’s been out of town doing shows and recording, and in a recent interview on Chicago’s WGCI radio station, he acknowledged the change has been daunting for his creative process: When I be in Atlanta too long I can’t write too many songs. I have to always come back to Chicago. There's nothing like the Chicago feeling." The travel may have ultimately been good for him, though, broadening his worldview and leading him to delve into newer ideas and to sharpen his focus. On Free Crack 3, he switches perspectives ably, from a survivor determined to better the lives of himself and the people around him (the Five Stairsteps-sampling "Things Will Get Brighter") and a 21-year-old with a little money in his pocket and some time to kill, like "Aww Man." Through all of it, he remains self-aware of the choices he’s made and how they’ve made him into who he is. On "Word Around Town," he chuckles, "Probably could've been a mathematician/ But a nigga made bad decisions/ Momma told me but I didn't listen/ Judge sent my bad ass to prison."

In lieu of struggling to keep up and stay relevant, Bibby has found success mostly by sticking to the program that got him here: consistent quality. While this tape marks the conclusion of the Free Crack series, he recently announced a debut, FC3: The Epilogue, coming next month. A few months back, Bibby posted to social media that he received his G.E.D and was now thinking of attending UCLA. For various reasons, it’s hard not to listen and root for him.