At 21, rapper Lil Bibby has the street knowledge and quiet confidence of a man twice his age. Hailing from Chicago, the city given the dubious title of the nation’s murder capital in 2012, he has lost numerous friends to gun violence. Bibby was forced to mature more quickly than the average youth due to his rough surroundings on the east side, which he characterizes as “probably the worst neighborhood in Chicago.”

As an alternative to hanging out on the streets, Bibby (given name Brandon Dickinson) initially started recording rhymes on his cell phone for fun at the age of 17. But he quickly realized he had a future in hip-hop when one of his first songs with friend and frequent collaborator Lil Herb became a viral sensation. “Kill Sh*t” caught the attention of Drake, who then added a clip on Instagram of him rapping along to the song. Bibby hasn’t looked back since, releasing three installments in his Free Crack series of mixtapes. The most recent, Free Crack 3, dropped November 27.

EBONY.com spoke to Lil Bibby about everything from his latest mixtape to Spike Lee’s Chiraq, the rise and fall of Slim Jesus, and his unapologetic Justin Bieber fandom.

EBONY: Congratulations on getting your high school diploma. Explain how Sway and Heather B inspired you to do that.

Lil Bibby: When I went in there, I really wasn’t thinking about a high school diploma. I didn’t see myself going back to school, but they were telling me to go back. They said they would throw me a party if I did. It still didn’t move me too much at first, but I just woke up one day and decided I needed to start doing it. It got to me.

EBONY: With the release of Free Crack 3, does that mean the end of the Free Crack series?

LB: It’s the end of it. No more free stuff.

EBONY: The features included a lot of other Chicago artists, such as Common, R. Kelly, Jeremih, Lil Herb and Tink. Was that done intentionally to give the tape more a Chicago vibe or did that just happen?

LB: It was just people that I was messing with at the time. I got Future on there and Jacquees. That’s two Atlanta artists. I got a lot of Chicago people on there too, but it wasn’t intentional.

EBONY: How did the collaboration with Future come about on “Aww Man?

LB: My A&R had the record and he just gave it to me. Then I ended up running into Future when they were recording What a Time to Be Alive in Atlanta and we just linked.

EBONY: What do you think a record like that can do for you if it takes off at the right time?

LB: I think that record is super-catchy. It’s a club record and it sounds good on the radio. It’s got the flow. I think it has the potential to catch. It might need a video and just a little bit more radio. A lot of people are feelin’ it in the streets.

EBONY: What was it like growing up with Lil Herb? When did you guys get into hip-hop?

LB: Uhh..it was cool. (laughs) We were just kids standing on the block, doing crazy stuff. I would say when I was about 17, so he was about 16. About four years ago. We were playing around with it at first, rapping over cellphone voice notes. We would have a beat playing in the background, then we would make a voice note on the phone. We would send it to all our homies, and the next thing you know everybody got it on their ringtone. We just went to the studio one time and made a CD with three songs. Everybody was riding around playing it.

EBONY: When did you guys realize you were good?

LB: When we did “Kill Sh**.” The type of attention it was getting in the little time that it was out. That’s when I knew it was bigger than we thought.

EBONY: Drake co-signed it and Kevin Durant tweeted out his appreciation when you guys dropped “Kill Sh*t.” What did that attention feel like for you at the time?

LB: That was crazy, man. Kevin Durant is one of my favorite players and Drake is my favorite rapper. That was crazy to know that, damn, I was just standing on the street corner and I got these people shouting me out, these people that I look up to. It was just… I don’t know. I can’t even explain the feeling.

EBONY: Have you gotten a chance to meet Drake or work with him?

LB: I met Drake a couple times. Drake is cool. I’m cool with people in his camp.

EBONY: Did you and Drake work on any music?

LB: Nah, not yet.

EBONY: You and Herb have collaborated a bunch of times. Have you guys ever considered forming a group putting out a collab project?

LB: We’re thinking about putting a group project out at the top of the year or February.

EBONY: Have you gotten a chance to see Chiraq?

LB: Nah, I’m actually supposed to be watching it today. I’ve seen the trailer.

EBONY: Did you like the trailer? What were your thoughts on that?

LB: I don’t know. I was expecting it to be a documentary of Chicago, but it’s nothing like that. Just from the trailer, it doesn’t seem like a documentary. Spike Lee must have tried to put his own message in the movie. I don’t know where he was trying to go with it. I’m waiting to watch it today though.

EBONY: Chance the Rapper and others tweeted about their problems with Chiraq. What’s the overall reception towards the movie in Chicago?

LB: I don’t know anyone that has seen the movie yet, but I know people that have looked at the trailer and not too many people are happy about it. I was thinking, “Why does Nick Cannon have his shirt off like he a gangsta?” (laughs) We know Nick Cannon for funny roles. I don’t know what made him do that. I don’t know who told him that was a good idea.

EBONY: Tell us about The Epilogue, your debut studio album coming out next year.

LB: I’m in street mode, so it’s probably gonna be a lot of street records on there. On FC3, I gave them a little bit of everything. I gave them the joint with Kells, the joint with Tink, and a couple other different joints. I think I’m gonna go mostly street with on this record. That’s how I’m feeling.

EBONY: What do you think it is about Chicago that’s producing so much young talent right now? Acts like you, Lil Herb, Chance the Rapper and Vic Mensa appear to be at the forefront of the next generation of Chicago MCs.

LB: Chicago is one of the craziest cities I’ve ever been to. It’s one of the realest cities. I don’t know how to explain Chicago. There’s a lot of sh*t going on out there. There’s a lot to rap about. I think people are just rapping about what they’re seeing. There’s a lot going on.

EBONY: Who’s somebody you would want to collaborate musically that people wouldn’t expect?

LB: I’ve been listening to Justin Bieber. (laughs)

EBONY: How do you feel about Slim Jesus and his movement?

LB: I knew what it was. I was probably one of the first people up on it because it was funny. It was entertainment. I’ve been doing this for a minute and I know the game is really entertainment, too. If you can entertain people, then you’ll [have some success.] I took it as entertainment. That’s why I shouted it out. I knew once people saw it, it was gonna stick with everyone.

EBONY: So you didn’t take it as him biting the drill sound?

LB: Nah. I was flattered a little bit, because he was doing exactly what we were doing. You can tell he was listening to me and Herb because of his whole beat patterns and cadences and everything. So I was like, yeah, he really watches us a lot.

EBONY: Did you see the video from one of his shows when he got the mic snatched from his hands?

LB: Yeah someone showed me that yesterday. I don’t know, man. He went out and said, “I don’t really do this stuff I’m talking about. I’m just rapping.” He shouldn’t have done that. Now people aren’t gonna respect him, so they’re gonna try him a lot of places. He’s gotta do something about that if he wants it to stop happening. (laughs) He’s gotta go up somebody head.