Lil Bibby: From the Streets to the Studio


If you take a trip through Chicago’s Eastside neighborhoods or Englewood on the Southside, or the Austin neighborhood out West, you’ll likely see a lot of abandoned buildings, liquor stores, and groups of young teens hanging on almost every corner, that may or may not be involved in illegal activity. A site that has become all too familiar for those living there, that seemingly will never change.

Rapper Lil’ Bibby can attest to that; It was his reality at one point. He grew up on Chicago’s Eastside, in one of the toughest neighborhoods the city has to offer, on 79th Street, and for a long while, he was one of those young teens that could be found hanging on the corner at all hours of the night. The excitement of the streets and fast money sunk its claws into Bibby at a young age, and wouldn’t let him go.

“I was grown when I was like 14 years old, man. Really, after 12 [years old], nobody told me nothing, nobody [ever] told me what to do. I was doing a lot of crazy stuff, man. I was in the streets; getting locked up every other day, and [stuff] like that.”

Lil’ Bibby had become used to run-ins with the law, it was like a regular occurrence for him, and though his rap sheet may be longer than most his age, deep down inside he always knew that he was capable of more. Bibby, whose real name is Brandon Dickinson, like most people, was a huge fan of music and spent a lot of time listening to his favorite artists, Drake, Jadakiss, and Jay-Z. You could even catch him playfully freestyling with his friends from time to time, but it wasn’t until going through the intake process at county lockup, after being caught with nearly 30 grams of marijuana did he come to the realization that the street life just wasn’t for him anymore.

“I had gotten locked up for like 30 grams of weed or something, and you know when you get locked up, you got to go through the intake process and that stuff, you know that overnight process, and they take you out the cell in the morning, and they transport you. I was in intake, and there was like a hundred and something people in a small box, like a little, little box cell, and we was all bunched up together. I was looking around, and it was all dope fiends and just dumb people. They were in there arguing, about to fight over dumb [stuff], and I was just looking around like, man what am I doing here?”

After his release, Bibby went all in with music, and it didn’t take long for his hard work to start netting results. Most artists will tell you that they’ve been at it since they were first able to construct complete sentences, with some never reaching the level of success they set out to, but after almost 9 months of focusing strictly on music, Lil’ Bibby got his first taste of success after releasing the track “Kill Sh!t,” with fellow Chicago artist Lil’ Herb in 2012 (above).

The track caught the music industry by storm, and today, has over 9 million YouTube views. It became so popular that it made its way to the iPods of NBA superstar Kevin Durant, and Young Money artist, Drake. They both liked the song so much that KD shouted it out on Twitter, and Drake sent a DM to Lil’ Bibby saying “the streets need that TAPE. I’m waiting on it. You and Herb the future.”


At the time, Bibby had yet to release a full project, just a few singles, and if he was ever thinking about giving up on music, his fans can thank KD and Drake, two of his favorite people, for keeping him going. In an interview with XXL Mag, he spoke on the moment saying, “[when DrakeDM’d me] I really had to come with more [stuff]. Drake scared me. So I went back into the studio, and we came up with ‘Water,’ ‘Whole Crew,’ [and finished off Free Crack].” There was a brief moment of excitement the young spitter felt after their recognition, and elaborated more on the feeling with Vita 10|17 telling us, “KD, that’s my favorite basketball player, so of course, I was excited about that. And Drake,that’s one of my favorite artists, so that was crazy too.”

Lil’ Bibby dropped his debut mixtape ‘Free Crack’ a month later on DatPiff, and has seen it soar to unimaginable heights. It’s been downloaded over 150,000 times, and streamed nearly 100,000 more times. Following the release, Lil’ Bibby’s national buzz continued to grow. So much that he was selected as one of XXL’s prestigious Freshmen and was featured on the cover of the Mag in May of 2014, alongside Ty Dolla $ign, Rich Homie Quan, and Chicago emcees Chance The RapperVic Mensa, and Lil’ Durk, and others. Surprisingly enough, Lil’ Bibby didn’t even know he was going to be on the list.

“I didn’t know about it until last minute, so it was a surprise. My manager couldn’t tell me, because if the information would have gotten leaked out man, it was a possibility of me being taken off the list, so they didn’t tell me. But it was dope, man. It was dope, seeing people that I listen to like, Rich Homie, and Durk and Chance The Rapper. And DJ Drama too. Me and Drama had met a couple of times, but it was good seeing him, and the people that I listen to.”

After receiving much acclaim and positive reviews from their peers, some artists would kind of sit back and enjoy it, but the soon to be 21 year old rapper was anxious to get back in the studio and keep making hits. Shortly after being featured in the XXL Mag, he released his second mixtape in a year, ‘Free Crack 2,’ hosted by DJ Drama. DJ Drama is known throughout Hip Hop for his Gangsta Grillzprojects with Lil’ Wayne, T.I., Snoop Dogg and other talented spitters. It’s also worth mentioning that Lil’ Bibby was able to get Hip Hop heavyweights, Wiz Khalifa, Juicy J, and T.I. to feature on various tracks throughout the Free Crack 2 mixtape.
bibbWhen asked about how it felt to be in a category with so many other successful artists that have been blessed with a DJ Drama hosted project, Bibby humbly responded, “hat’s a big accomplishment for me. I grew up on the Gangsta Grillz. The Dedications [by Lil Wayne] and all that, Trap or Dies [by Jeezy] and [stuff] like that, so that’s a big accomplishment, but I knew Drama for a long time. I had known him for probably a year before that and he actually was supposed to do Free Crack 1. He was supposed to host Free Crack 1, but I was kind of messy with the music, man, and had music all over the place.”

With ‘Free Crack 2,’ Lil’ Bibby took a slightly different approach to creating the project. After sitting down and writing out a lot of the tracks on his debut, Bibby confessed that for ‘Free Crack 2,’ a lot of those tracks were freestyles, a habit he’s gotten into with a lot of his songs as of late. “Right now I’m freestyling most music, the young emcee stated. “For Free Crack 2, I don’t know, I’m getting in a process where I can’t write. It’s hard for me to write now. I know that sounds crazy, but I can’t sit down and write a song. I just get a beat and I just got to get in the booth and record, like, as soon as I get a beat or I’ll forget.” It’s a process that seems to be working for the up and coming star; It’s gained him over 200,000 downloads on his most recent release, and endorsements from some of the game’s hottest MCs.

As for what he has planned next, Bibby is hard at work on his EP that he plans to release next month in March. He’s already recorded over 40 songs so far, and more than half of them are freestyles. Lil’ Bibby is also developing a North American tour with plans to hit Denver, Detroit, and of course Chicago. And even Canada.  He also has his sights on venturing over to London soon saying, “I always get a lot of stuff about London, it’s a lot of fans over there, so I think I need to touch London.”

After 2 mixtapes, nearly 500,000 total downloads, and more YouTube views to count, Lil’ Bibby promises fans he isn’t going to slow down any time soon. He doesn’t shy away from acknowledging his success up to this point and  is highly appreciative of it, however, he remains humble through it all. And while most in his position would be thinking of cashing in off the first big contract placed in front of them, Bibby isn’t concerned with signing a major label record deal at this time. He remains focused on simply working hard and perfecting his craft, something he picked up from Juicy J and T.I. Both artists often tell him “you gotta outwork everybody,” and he’s making music everyday, doing just that.


In such a short time, Bibby has gotten a lot of attention from mainstream artists like Drake, and even Jay-Z, but don’t expect to hear a track with either artist anytime soon. Though, he does often dream of one day making music with both, right now, he doesn’t feel he’s quite at the point to request a feature from either just yet. When asked what he feels he needs to do before that dream can become a reality, he didn’t hesitate to say, “I’ve got to get right before I come to [Drake]. I wouldn’t even want to get a Drake record too early. I would want to have all my ducks lined up before I even try to play the Drake card.” When questioned about what he means by getting right, he went on to explain that, “If I get my own song on the Top Ten Billboard, then I think that’s getting a little right,” he said laughing.

It’s a goal that doesn’t seem at all too far-fetched for a young man who has overcome so much, and seen more in 20 years of life than most have in 3 lifetimes. Lil’ Bibby has accomplished everything he’s ever set his sights on, and has a music future as bright as the sun on a mid summer Chicago day. In his own words, “I kind of always knew I could do stuff, I always knew I could do almost anything. I was always smart, and whatever I put my mind to, I get done.“ And there’s no doubt in anyone’s mind that getting on the Top Ten Billboard chart and doing songs with Drake and Jay-Z will be any different. Drake might have been on to something when he proclaimed Lil’ Bibby was the future, and Lil’ Bibby is determined to make that opinion a fact.

If you haven’t already, download Free Crack & Free Crack 2 from DatPiff for free, and stay up to date with all things Lil’ Bibby by following him on Instagram and Twitter.


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