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Chicago’s thriving music scene is nothing new. During the Great Migration, blacks fleeing the Jim Crow south, African Americans went to northern cities and brought with them their country slang, country ways and powerful music.

Mississippi bluesmen such as Muddy Waters, BB King and Howling Wolf migrated to the Windy City with their country tunes and are now considered musical legends. Eastside Chicago MC, Lil’ Herb, is just one of many Chicago artist with deep musical roots that began in the Magnolia State and spread to the promised land of Chi-town.


As of now, Chicago is the breeding ground for Hip Hop’s next superstars. For instance, Lil’ Durk signed a deal with the iconic Def Jam Records. Durk is also signed to French Montana’s Coke Boys imprint. Also, Lil’ Reese and Chief Keef have deals with Def Jam and Interscope, respectively.

Up next is eighteen-year-old Herbert “Lil’ Herb” Wright.  Lil’ Herb’s potent storytelling is reminiscent of a young Jay Z, but more gangsta. While listening to his street-acclaimed,“4 Minutes of Hell,” one gets tense, as if the danger of Herb’s hood, 79th and Essex, is creeping through the speaker and watching his/her every move. So, you listen and hang on to every word that Herb speaks. His lyrics are packed deep with anguish and pain, like a Mississippi bluesman.

Well, Herb’s, and many other Chicago artists, potent storytelling is rooted in Mississippi blues.  Herb’s great-great grandfather, Leonard “Baby Doo” Caston, was a successful blues singer from Sumrall, Mississippi, who, as a member of The Five Breezes, once performed for President Dwight Eisenhower. One can hear the musical similarities in Herb and his great-great grandfather. On Baby Doo’s, “I’m Gonna’ Walk Your Log, he sings, ‘Awww/Your bread ain’t done/Awww, your bread ain’t done/Awww, ya’ life that way/You cooking cabbage greens, but ya’ bread ain’t done.” It’s clear that Baby Doo has experienced something or many profound things in life.  Profundity makes ones vision clear and makes for simple, but profound lyrics. Hence, Lil’ Herb’s 4 Minutes of Hell 2.

But, Herb’s musical roots don’t stop with Baby Doo. Doo’s son, Victor Caston, which is Herb’s Grandfather, was a member of 1960s R&B group, The Radiants. They crooned love songs. Herb croons about the love also, the love of his homies. On the scary, Lil’ Herb Freestyle, Herb raps, ‘M.O.B./fuck a bi***/I put the block the first/Cause that’s where the money at.” If fact, Herb loves his homies so much, that his latest mix-tape, Welcome To Fazoland, is named after his deceased friend, Faison.

Herb knows murder all too well. His deceased uncle, Kay-Tone, rapped alongside Legendary Traxster as a member of D 2 Tha S. They also produced tracks for fellow Chicagoans, Po Pimp and Twista. As one listens to D 2 Tha S’s, Caps Get Peeled, you can hear the effects of Mississippi slavery, hangings, Jim Crow and disenfranchisement. All of which birthed blues, R&B, rock & roll  hip-hop and hip hop’s next superstar, Lil’ Herb.

Lil’ Herb spoke with The Source about violence in Chicago, getting advice from Common, success and much more.

 How much of an influence did your uncle have on your music career?

Not really, musically. Because when my uncle passed I was only 13 years old. I wasn’t even rapping then, I was just listening to music then. Of course, I liked his shit. He was one of my influences when I started rapping. But, back then I just looked up to him like my uncle.  I was around him a lot. I held the upmost respect for him. Then I stared rapping, it was a coincidence. I just kept going hard at it, you know? That’s what he would’ve wanted anyways.

Are you familiar with “Livin’ In A Hellhole” by D 2 Tha S? There are some similarities. 

Nah, I don’t remember that.

Your grandfather played blues around the house, so are you into other genres of music?

Nah, I ain’t never get into blues. That’s just my grandfather, he was into music, he played that stuff around the house. But, that was way back in the 60’s, you know I ain’t hip to none of that.

So, what artist did you grow up listening to?

I grew up listening to Jadakiss, Jeezy, Gucci [Mane] Lil’ Wayne, Juelz [Santana,] you know, people out the Dipset.  I fuck with Reasonable Doubt and Scarface. That’s who I fuck with, people who got lyrics.

When I talked to Drake, he said that he played some of my shit for Jay Z and he was fucking with it. That was the last I heard of it.  Drake shouted me out on Hot 97 and on Twitter. (Drake Tweeted lyrics from Lil’Herb and Lil’ Bibby ‘s, “Kill Shit”).

Do you talk to Drake often?

I got a new phone and lost his contact. But, I’ll run into him again.

So, when did you start rapping?

I got into rapping when I was 15 years old.  I started rapping with [Lil’] Bibby and couple of other homies in the hood.  We just fucked around with the rap shit. I started rapping on cell phones. I was rapping like, 60 second shit on the phone. I always knew how to rap, but I just was never on that. I was playing ball and shit when I was a shorty.  I was familiar with music because of my uncle and grandfather, he had a studio and used to be fucking around in there.

Do you remember the first rhyme you ever wrote?

Yeah, I remember the first rhyme I ever wrote. I ain’t going to lie to you, I remember almost all my raps, like 80 percent of them.

Can you spit the first the first rhyme you ever wrote?

I first rhyme I ever spit went like, “I get it on Faison/Ask about me/Catch me on the block, big toolie/Big steal/ fuck around with….’ Damn. [Laughter] I forgot that shit. That shit is so old. But, I can remember it though. It’ll click.

No doubt.  The content hasn’t changed. So, tell me what it’s like growing up on the Eastside of Chicago?

Growing up on the Eastside. It’s the safest place in the city, but you got murder, violence. For me, growing up, I wouldn’t say I had a real hard life, but you know, I wasn’t born with no silver spoon in my mouth. Growing up where I am from, it ain’t nothing nice, you know? It was violence, killing, all type of shit. That’s what I rap on Fazoland. I tell a story, paint a picture of who I am and where I’m from.  My childhood wasn’t the best childhood, but I can’t complain, I’m here, I’m doing something with myself. I’m just trying to make the situation I’m in a better situation.

On the Eastside is where you met Bibby?

Yeah, that’s been my homie way before this rap shit. I knew Bibby since I was ten.

 What’s N.L.M.B.?

Never leave my brothers.  No Limit. That’s where we from. Me and my homies, just a group of niggas.  Growing up, it was real hectic, we had to survive out there and it was us, we was all we had. N.L.M.B., No Limit Muskegon Boys.

Are any of y’all affiliated?

Nah, it’s a brotherhood. It ain’t no click, no gang or nothing like that. It’s a brotherhood. We ain’t affiliated with no Vice Lords or none of that. I don’t be on the Southside or Westside, we straight Eastside. I’m known on the Eastside.

I expand myself everywhere I go. I’m free to go wherever I want. But, Eastside, that’s where I’m from, that’s who I am, you know? We not associated with no G.Ds, Vice Lords or none of that.

Ok. Let’s switch gears. So, what major labels are reaching out?

As far as labels, I’ve been meeting with everybody. But, I ain’t trying to jump in that lane right now. I’m just working, dropping songs, making songs, just trying to make myself better, my situation better. I’m not in no rush to jump in no deal with no label. But, I’ve been meeting with labels, flying out, building relationships with people.

Are you touring?

Yeah, I’m touring. Starting to tour more now. Got a lot of shows coming up in different cities. I just been working on my mix-tape trying to get my mix-tape out. So, now the work is about to start really kicking in.  That was just the beginning.  Now it’s time for the real work.

So, you have another mix-tape coming out?

Yeah, I got another mix-tape coming soon. I’m try to work on it, but I don’t have any dates for it though.

Have you started recording new material?

I’ve been dropping shit. I got songs that I can put on the next mix-tape right now that I didn’t throw on my first mix-tape. I could’ve threw twenty, twenty-five songs on my first mix-tape, but I only threw 16. I got songs that I didn’t use from my first mix-tape that I could’ve used for my second mix-tape. But, it’s about working with me.

It seems like you just blew up over night. Have you experienced any roadblocks?  

I kind of expected it, but I ain’t expect it to be like this. I’m starting to see that I’m in a real good situation. And, I can have a real good career in the future. But, it started with just me and my homies, just rapping.  Coming up in the struggle. It was a war going on in our hood. I was just rapping, getting by, trying to stay out of the way. Then it started going crazy, I was dropping videos. Then it started going from hundred-thousand, to 1 million, to 2 million, to 5 million, to where I got on like now, independent without a label. It just blew up. A lot of people got good situation in Chicago. I like that the spotlight in Chicago. A lot of rappers in Chicago, artist that I know personally and built relationships with, come from nothing like me and are doing something with themselves. So, that’s real good. But, it’s just about working hard and staying humble. I don’t let that shit get to me cause that ain’t no real success. I want real success with my career.

So, what’s real success?

Real success, I define is being at the top. That’s what we in… Well, I don’t know what people in it for. That’s what I’m in it for, I’m in it to provide for myself and everybody around me.  I’m trying to be a millionaire, a billionaire possibly. I’m really trying to go as far as it can take me. You know what hard work will do, it’s just about working hard, you know.

Five years from now Lil’ Herb will…?

Five years from now, I see myself doing movies. Five years from now I see myself having successful albums out, a lot of milestones. Of course, touring, doing shows, filling up big arenas. Five years from now I see myself selling out arenas.

Is your music career the reason you dropped out of school?

Yeah, it was a lot going on as far as the music and other shit going on in Chicago. Chicago a real hateful city. It’s a lot going on, but you know it’s a good city. I love my city. I ain’t just give up on school, I’m just giving it a break. I was going out of town a lot, I was missing test and shit. It was a lot of shit.

Do you feel relaxed when you get to leave Chicago? 

I got my guard up everywhere I go, bruh.  L.A. wherever, I’m always aware of my surroundings, I always got my guard up. If I’m at the crib I feel the same way, I just know to keep my head up. I lost five of my homies, close homies all in one summer. I know Chicago ain’t a safe place to be. My guard is always up, bruh.  I ain’t worried about it, What’s going to happen, is going to happen.

Do you see Chicago getting safer?

I mean, it’s been so many people saying what can be done and what can’t be done, I don’t know what can be done. I can’t just say, ‘this is what can stop the violence,’ because it’s been violence. It’s been killing, it’s just worse.  I mean, that’s what’s going on with the kids out here. I can’t really speak on it. When people kill people, that’s what happens. When somebody kill someone close to you and you feel like you want to do something about it, it’s going to happen and can’t nobody change that, ain’t nobody going to make nobody stop killing.  Can’t nobody take every gun off the street. No president, no police officer, nobody.

Are you involved in any type of activism yet?

If I can expand my career, I’m going to reach out to my community and the people in my city. I’m going to try to be a good influence to the kids in school. I ain’t rapping about, ‘you should go kill people’ and shit like that.  I’m rapping about real stories. Shit that happened to me and the reason why I am the way I am.

Do you want to talk about how some your friends, specifically Faison, lost his life?

Nah, I don’t really want to get into that. Nah, I ain’t going to talk about that. That was the first person in my age group that died. There was people that was older than me [that died] but that was the first person that was my age that was killed.

Ok. So, have any of the older artists from Chicago reached out to you?

Common, the big homie, Common reached out to me. Common just hit my phone a couple weeks ago to see how I was doing. He gave me a verse on the intro of his album.  I fucks with Common, that’s about it.  I had bumped into Twista one time at a store.  Like, when I was growing up, Twista was at my grandmother’s house with my uncle and them doing records and just fucking around.  Traxstar and all them used to fuck around. But, that was as a shorty, I don’t really know him like that.  The only person that has reached out to me, that’s real successful from Chicago, is Common.

What did he say to you?

When I first spoke to him, he was like, ‘keep it up.’ He told me that he like my style and the way that I carry myself.  And with my work ethic, I can go real far and he told me don’t ever stop doing the shit.

As told to Darryl Robertson (@darryl_robertson)