Generation Next: Lil Bibby talks rap, rolling solo and stopping crime

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To be clear, interviewing a rising rap star whose first mixtape features a song titled “Tired of Talkin” probably primes everyone involved for a terrible conversation.

Except it wasn’t.

Lil Bibby, born Brandon Dickerson, is extremely measured and careful with what he proffers, but he doesn’t seem tired of talking at all. The 20-year-old talks about moving from school to school as a teen. He talks about how, years ago, he fell into car theft because he was bored and didn’t have anything better to do. He talks about the death of a friend and leaving crime behind. He talks about his mom, his two brothers and his sister. He talks about his new mixtape, “Free Crack 2” (which, ahem, is not actually about what you might think it is about), and he talks about his desire for stardom juxtaposed against his desire or a quiet life.

[one_third] Alex Wiley with Lil Bibby Where: Bottom Lounge, 1375 W. Lake When: Doors open at 8 p.m. Tickets: $25 Info:, (312) 666-6775 [/one_third]

Stereogum has hailed him the “young Chicago rap zeitgeist” and, like other up-and-comers have before, he’s performing 9 p.m. Thursday at The Bottom Lounge (He’s part of Ty Dolla $ign’s “In Too Deep” concert tour.)

But first things first.

Despite knowing and working with other Chicago hip-hop heads including Lil Herb, Young Chop and Chance the Rapper, he has learned the value of rolling solo.

“I stay to myself,” says the lyricist whose baritone vocals don’t initially seem to match his babyface. He’s seen several friends get shot and admits that he himself is no angel. “It’s always beef in Chicago. I don’t want to pick no sides.”

Perhaps that’s why, when he comes to the interview, he is pretty much by himself. No entourage. No obnoxious bodyguards. No fanfare. He’s wearing a preppy sweater (“I had court today, so I put on a sweater”) and fancy socks embroidered with his name. His Air Force 1s are squeaky clean. He’s carrying only one plain cellphone. And unlike others, he puts his phone on mute and keeps it in his pocket until the interview is over.

Outside of being nonspecific about his court case — and talking less and less — when discussing his experiences with car theft, he’s pretty open. Here are the rest of his basics: He’s biracial. He’s a skilled basketball player (hence the nickname Bibby). He’s 6-foot-1. He doesn’t put on airs. He’s thoughtful. He reads. He made XXL magazine’s Freshman Class issue for 2014 along with fellow Chicagoans Lil Durk, Vic Mensa and Chance the Rapper.

Related: XXL’s writeup of Bibby

His much-anticipated sophomore mix tape — which was hosted by DJ Drama and features cuts with R&B soul crooner Anthony Hamilton, Juicy J, Lil Herb, Wiz Khalifa and production by Chicago’s own Young Chop — saw half a million downloads within 30 minutes of its August release. To date, according to Datpiff, the mixtape, hosted by DJ Drama, has had 1.35 million listens.

Those are pretty good numbers, says Tyree “Drama” Simmons, who appreciates Bibby’s unique vocal sound and “depth.”

“I been following Bibby for some time,” says Drama, the Gangsta Grillz series deejay and A&R team member at Atlantic Records. “When it comes to Chicago, he’s definitely one of those dudes. I just liked him, because I feel like he has a lot of soul and the life of the city in his music. It’s quite capturing, as well, the way he mixes thoughtful ideas with street music and brings the two together.”

That music is what’s keeping Bibby off the street and he thinks that if others had similar work opportunities, it might cut crime — or at least cut car theft.

“There need to be more ways for people to get money,” he says, specifically referring to his old neighborhood around 79th and Essex. “Money is very important. I used to be a little crazy, [but now] I know it’s a bigger picture than all that.”

Related: has the details on the XXL “Freshman Class” writeup

He’s also got a mentor — an unnamed, higher-up mentor, who recommended he start reading books like “The Art of War.” He says he formed his own limited liability corporation, Grade A Productions, which is how he sells his merchandise. Earlier this fall he also hosted a bookbag giveaway for kids who lived in the neighborhood of his old elementary school, the Bradwell School of Excellence.

Like others in Chicago’s music scene, he has been doing a lot of work outside the city. After spending most of his early career literally recording songs inside of a closet, he now can claim space and time in an Atlanta studio. He’s not always at home, but when he is, he’s learning how to deal with newfound celebrity. It’s a bit unsettling to walk into a building in downtown Chicago and draw a crowd of people who want selfies, he says, but he’s aware of the blessing and trying to stay gracious.

But, perhaps following an alleged all-the-business-is-on-Twitter tiff between him and another rapper last fall, he has also decided that there’s a time and a place for all conversations, which is why his social media timelines are (now) pretty much drama-free.

“You can’t say so much on Twitter,” he says, perhaps referring to past moments of talking too much or perhaps referring to his hit song, “You gotta be vague.”

Reach Adrienne Samuels Gibbs at or on Twitter @adriennewrites


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