His new, and debut, mixtape Free Crack is capping the year for a Chicago rap scene that has mutated but remained as fertile as ever. Bibby is gruff and direct, without the pop inclinations of the city’s current stars or the playboy swag of his frequent partner Lil Herb. But he is on the way to establishing his own sound, one that folds the bluster of early-aughts New York into drill’s rattling template. It’s not a stretch to think that one day soon Bibby might rap over a Just Blaze beat.
But last week he sat in FADER’s conference room, talking about his career so far, DM’s from Drake and Iman Shumpert, and why he bristles at the term “drill.” All the while, he munches incessantly on Welch’s strawberry fruit snacks.
Stream: Lil Bibby, “Water”
When exactly did you start rapping? Three and a half, four years ago.
What’s the first music you remember hearing as a kid? My sister had me listening to Nas, DMX, Bow Wow, Eminem… that type of shit.
So that’s kinda what you came up on? Nah that’s what I was forced to listen to. I came up listening to Lil Wayne, Gucci.
How did you get into rapping? I don’t know, I just didn’t like a lot of the music I was hearing. I was always a big music critic. One day I was at my friend’s house and we was just playing the instrumental. We had pulled out the phone and they was recording it while the instrumental was playing on the speakerbox. We just started rapping and then they recorded, and we sent it to all my friends and everybody put it as their ringtone.
Do you remember what instrumental it was? It was a Cool & Dre instrumental or something. “Chevy Ridin’ High” or some shit.
When did you first start to think that rapping was something you could do seriously? We went to the studio one day, me, Herb and my other friends. We recorded like three songs and put them on a CD and then we put it on YouTube. It took off from there. All my homies was riding to it, and everybody just encouraged it.
Have you and Herb always been working together? When did that start to happen? Ever since the start we been working, you know. I don’t remember, like — I probably recorded a song before him, but the second time we went to the studio it was me and Herb.
That sorta demo thing, was that in a bedroom? Somebody’s closet.
When did you start recording in more professional environments? Probably a year ago. Like, a year or two ago. But I still prefer the closet. Me and my producer it just seems to work. When we in the house somewhere you don’t have no time limit…
No distractions. Yeah.
How long have you been working on the mixtape? What was that process like for you? Actually, some of the songs are like 10 months old. Some of it is weeks old. Probably about nine months, but the mixtape was supposed to been out. But we just released all the songs and decided to start from scratch.
Why’d you start over? I was finna put it out earlier, but when Drake DM’d me, he was like I’m waiting on the tape, the streets need it. I was like, Man, I gotta go back in the studio. He put the pressure on me.
What was that like when he reached out to you? I don’t know, I was a little shocked. I was scared, cuz I was like, Damn, this mixtape probably ain’t ready to be heard by no Drake.
What were some of the songs that came out of the second session? “Whole Crew” produced by Hit-Boy. “Water.” A song called “See Me Down.”
What direction did you wanna go in with the mixtape? I just wanted to express the type of shit I was going through, the type of shit I was seeing in Chicago. I wanted to show a little bit of versatility. There’s really no subject matter—I just wanted to showcase the versatility.
There’s a line on the mixtape where you say “This not no drill shit.” How do you see yourself being different than what most people would consider drill music? I don’t like that category, how y’all put Chicago music in that category.
Why’s that? Well I see why you did it, cuz a lot of artists, all they talk about is shooting, killing, smoking. So y’all call that drill. But I don’t think I do that. I talk about the shit I go through on a daily [basis]. When I make a song called “Stressing,” it was a lot of shit on my mind. I was going through some type of shit. So, I don’t only do that type of shit.
So you think you’re a little bit deeper? Yeah. You can hear by the choice of beats that I pick, the type of songs that I make.
Drill music obviously opened some doors for you, but do you feel like Chicago’s reputation has boxed you in at all? Nah, not me. But some of the kids, that’s all they could talk about, because… I don’t know, I don’t know if that’s all they see that’s why they do it. I dunno why people can’t talk about other shit in Chicago.
Do you think it casts the city in a negative light at all? Some people are scared by the music that comes out of the city. That’s what we experience so that’s what you need to hear. You ain’t gotta be scared of Chicago. Just go downtown. Don’t come on the south side if you don’t want no trouble.
There was sort of a moment there where Drake kinda blew you guys up on his Instagram… what was that like? Drake didn’t blow us up like that.
Maybe not in Chicago, but a lot of people I think first found out about you guys through that. Was that not something you saw as a big deal? Nah, that was a big deal—cause that was my favorite rapper at the moment. He the biggest rapper right now. That shocked me. That was a big deal.
Have you spoke to him at all beyond DM? That nigga cool. He cool.
That’s all you wanna say? [Laughs] He cool.
When you were putting the mixtape together, you didn’t really go outside of the city for collaborators. Yeah, that’s exactly what I wanted to do. Just keep it in the city. Just me and the people that I mess with. A couple of my homies they got a lot of connects, they were trying to get Game and all these other names on there. But I was like, Nah, not for my first tape.
Do you find it tough to say no? Yeah, yeah, I don’t really like saying no. That’s why I like to stay out the way. I don’t like to be seen. Cuz when somebody run up on me like Bibby, I got a song for you I’m like Just send it to me. I don’t like saying no. But I just try to keep myself busy.
How do you write songs? What’s that process like? I write a lot of songs on my phone. I freestyle a lot of hooks, too. Very few songs I might freestyle the verse four bars at a time.
When you’re writing a hook what kind of concepts are you trying to think about? When I hear a beat I kinda… Whatever mood the beat put me in then I try and think of the concept that match the beat’s mood then I put it into words. You gotta think of the melody and the rhyme scheme…
Was there a certain mood you were kinda going for with the mixtape? The mixtape all over the place. Some of the earlier days it was the drill music. I was turnt, I was having fun. But when shit started getting crazy, man… the soul samples, man, I started expressing how I was feeling.
When you say things started getting crazy, do you mean when people started paying attention to you? Yeah, that’s the type of shit. All the attention, all the fake fame or whatever you wanna call it.
Is it tough being in Chicago and having that sorta attention? To me, to me. I don’t really like a lot of attention. I don’t know if you see it but I don’t like talking a lot, man. I don’t like people messing with me, man. Now, I can’t walk down the street without someone messing with me. Everybody want something, whether it’s nothing but a picture, they want something. My homies… I don’t know. People just fake, man, nowadays. People wanna be your friend now.
But back then they didn’t. What Mike Jones said.
Do you think people look to you as someone who’s bringing something that wasn’t in the city’s music scene? Yeah, yeah. I don’t know, I don’t think there’s anybody in Chicago that’s doing what I’m doing. Or, they probably can’t. [Laughs] I just make songs… I express a lot of feelings in my songs. It’s everything real.
That’s the kinda music you connected to before you started rapping? I like to get something outta the music. I ain’t gonna lie, sometimes I play the Keef when I wanna nod my head, get turned up. But the music I think stick around is the music that got a message to it, you can get something out of it. Make you think, or make you wanna do something, you know.
Have you heard from fans, like, Bibby this track spoke to me? I was just a few days ago with Iman Shumpert from the Knicks. He told me Man, I was so glad that you came up with this tape at the time you did, man. Cuz I needed that shit, I was going through some shit. Don’t never stop rapping.
Well the Knicks are having a terrible season, maybe you were able to help him out. [Laughs] How you gonna do my homie like that?
How did you guys meet up? He hit me on Twitter like a minute ago. I just found out he was from Chicago, so that’s one of my homie’s homies for real, though.
You ever used to play ball? Yeah I used to play ball, man. My name Bibby, man. Lil Bibby.
Is that where it came from? Yeah. I had that shot.