Who Is Lil Herb? Redefining Drill With Chicago's Toughest New Talent

We spoke with Terror Town's favorite son, Chicago spitter Lil Herb. One of Chicago's most promising talents, Herb is redefining the rep of drill.

Not Available Lead
Image via Complex Original
Not Available Lead

What exactly makes a city's scene hot? You can argue that it's just an accident of history—a bunch of talent, randomly distributed, just happening to wash up on the shores of (let's say) Lake Michigan. The reality, though, is so much more complex, as real-world forces align to create a humming ecosystem: the spaces, both real and virtual, needed for it to exist. The people, and their ever-shifting economic and social backdrop. Then there is perception: the windows between this world and the outside. And the shadows, the spaces beyond the range of an onlooker's vision. There are channels that allow influences in and let art out; there's blockage, the limitations that distort those sounds, an evolutionary telephone game which gives a scene its particular shape, distinct from its influences above and outside.

In Chicago's case, it's a city shaped by geography and history, an urban landscape—Chicago is a city of nearly 3 million, the third-largest in the nation—and a Southern people—the bulk of its black citizens migrated from the South in search of work during the Second Great Migration. Many still have family in Mississippi; the music that plays in its clubs and at its parties reflects this lineage.

It's also a scene—you may have heard—with a number of new, young stars: Chief Keef, Chance The Rapper, Vic Mensa, and now Lil Herb, each their own center of gravity, operating in reaction to one another. Each represents an audience with a specific sensibility, a constituency of varying size. Herb's, no doubt, will rally around his debut tape, Welcome to Fazoland, out today. If the tape has a purpose, it's to present the blueprint for Lil Herb as a major artist. To suggest Herb is rooted in, but transcending, the laser-sight-narrow gun raps that have thus far been his stock and trade.

If Lil Herb didn't exist, it would be necessary for that constituency to invent him. A rapper is at once the product of the urgent needs of his audience and his own self-image, his own story—even if the latter only tenuously implies the former. On that first level, Herb's a rapper for those who like everything about Chief Keef except the way he raps. Herb is a spitter, a rapper with a dexterous double-time and a variety of intricate, nervous flows that dart across the beat. No larger a star than Drake has emulated him and his frequent rhyme partner Lil Bibby on-record. But Herb comes from a similar background to Keef. Still just a teenager, his bars revolve largely around the mastery of violence. He is a product of 21st century Chicago gang culture, and represents a crew that holds down Roc Block around 79th and Essex, in the neighborhood known as Terror Town.

Loyalty is hard to come by where I’m from. So we hang with people who we knew, who we grow up with. - Lil Herb

Like many rappers who spit from a street's eye view, he tends to talk about his rapping less in terms of its technical aspects and more for its content. "People tell me I’ve got my own style," he says. "I bring originality, but I rap just about my lifestyle, what’s going on, certain situations I’ve been through."

If that sounds like Keef, his rapping style, his controlled spray of words, does not. It is that level of mastery that has drawn the ears of listeners looking for an alternative. One of those people was Mikkey Halsted, a Chicago hip-hop vet who came up with Kanye West, but watched his own career fumbled by the industry—even as artists he collaborated with, like Lil Wayne, went on to find stratospheric success.

Like everyone interested in Chicago's young hip-hop scene, Halsted became aware of Herb by peering through the YouTube window. "One of my little cousins—similar to Herb’s age—was getting into some street stuff," he explains, "And I had him come to L.A. 'til things cooled down a little bit. He was into the whole youth movement going on in Chicago. I said, 'Man, there’s got to be a shorty from the city that’s about that life that raps but that can really, really rap. That’s really talented. Who’s the best rapper?'"

Halsted's hallelujah moment came when his cousin pulled up a video of Lil Herb spitting a freestyle for Urban1on1.com. In the video, Herb's booming voice belies his age. He spits with a steady, atypically deliberate style, even as a CPD SUV pulls up beside him.

"It’s like—I lit up," Halsted said. "I was like, 'Man, he the one. He the one right now.' I ran all over the studio showing it to everybody I could show it to. It made me proud. Like he’s got the talent of Jadakiss, like real spitters. I look at him like he mix of Jay Z and DMX. I see greatness in him."

These are bold words, but Halsted put his money where his mouth was, and reached out to become the rapper's manager. As it turned out, Halsted's little brother was a co-founder of Urban1on1, and had shot the “Kill Shit” video. (This was the video that attracted the attention of Drake, who tweeted out Herb's lyrics from the song last April.) Through them, Halsted reached out to Herb. "I could tell he didn’t even really care about rap at that time like that. He’s like, 'I’m in night school, bro. I’m going to hit you back.' But he was respectful."

This is where, at a deeper level, Keef and Herb also differ. Whereas Keef has taken to his role as hip-hop's youngest heel, Herb's position is one of reluctant nobility. Hip-hop wasn't Herb's first choice. Like a street rap Bo Jackson, he took to the streets, to rap, and to basketball. He's been shot (in the foot) as a result of the first. The second has led to local fame and national interest in his career as an artist.

My first couple of raps you can tell I hit a fast tempo, but I can rap slow too. And I just got better at it, so now it’s just second nature. - Lil Herb

And the third, suggests one source, is at the core of the story he has to tell, which is one of friendship and loyalty as much as it is one of societal dysfunction and violence. Herb's neighborhood, traditionally, were "moes"—the colloquial term for a member of the Almighty Black P. Stones street gang. Herb is also a member of No Limit, his more localized crew. Traditionally, the P. Stones are enemies of the Lakeside Gangster Disciples. But the No Limit crew played basketball with members of the Muskegon Boys, a crew aligned with the GDs. Both sets bonded over the game and became friends. Ultimately, both broke off from their parent organizations and became renegade factions, joining forces to become N.L.M.B., or No Limit Muskegon Boys. In an effort to suggest a more positive direction, they've since rechristened the crew "Never Leave My Brothers." 

"We all just grew up, we from the same neighborhood," says Herb. "The people that I hang with I knew for a long time, my friends growing up. We try to keep our circle small. It’s really a loyalty thing. Loyalty is hard to come by where I’m from. So we hang with people who we knew, who we grow up with. Some people stayed, some people branched off, some people got killed."

It has been a path beset by tragedy. Halsted tells the story of the backdrop for the "All My Niggaz" video shoot. After local graf legend Kane-1 finished the R.I.P. tag, Halsted told Herb to give Kane the names of his friends who'd passed on, so their names could be added to the mural. Herb named seventeen people.

This has obviously and evidently shaped Herb's music. As has Chicago as a city, more directly; one of his earliest, best singles was the DJ L-produced "Gangway," a very explicit nod to Chicago's particular urban topography. It's also evident in his lyrics: "Young nigga, always hangin with them older guys/We was bangin, slangin all the white but we ain't Oberweis." 

But as much as Chicago, basketball, and the streets have defined Herb's life, in his veins runs a musical heritage going back generations. Herb's great-great grandfather was Leonard "Baby Doo" Caston, a blues musician born in Sumrall, Mississippi, and raised in Meadville, who moved to Chicago in 1936 at age 17—one year younger than Herb is today. He recorded with Willie Dixon. One of his most well-known solo songs was 1940's "I'm Gonna Walk Your Log."

His son, Herb's grandfather, was Victor Caston—a member, as has been reported previously, of the Radiants, a '60s R&B group whose hits included "Ain't No Big Thing,""Baby You Got It," and "Hold On."

That last song, though, was written and produced by Victor Caston's older brother, Leonard Caston, Jr., also a member of the Radiants. Leonard, Jr. would go on to become a songwriter and instrumentalist of great renown, working for Motown, playing piano on Fontella Bass' 1965 R&B No. 1 single "Rescue Me," and co-writing such R&B/dance classics for Eddie Kendricks as "Keep On Truckin,""Girl You Need a Change of Mind," and "Boogie Down." In 1975, he received a Grammy nomination. He also wrote and recorded "I'll Keep My Light In My Window," an R&B standard recorded by everyone from Marvin Gaye to Ben Vereen.

But more relevant to Herb's own creative output was the music of his uncle, Victor Caston's son Trevor Caston—known throughout Chicago as Kay-Tone. Kay-Tone doesn't have much of a national profile, but he was a seminal recording artist as one half of D 2 Tha S. (The other half was Legendary Traxster, who went on to produce Do or Die's "Po Pimp," Twista's "Adrenaline Rush," and songs for Cam'ron, Scarface, Lil Boosie, Mystikal, and Mariah Carey.) D 2 Tha S were known for a series of singles they released in the early 1990s, when Chicago was still an emerging marketplace. At the time, Chicago's hip-hop scene was divided between Dem Dare—a more true-school hip-hop scene that revolved around the parties of DJ Twilight Tone and produced beatmaker No I.D.—and the Ill State Assassins, a more street rap-oriented crew that included D 2 Tha S, EC Illa, and Twista.

D 2 Tha S was fated for local fame. Although they had beef with Treach of Naughty By Nature and released a handful of classic singles, they remained local legends. D 2 Tha S's "Doomsday" dropped the same day as the Traxster-produced "Po Pimp." One sold hundreds of thousands of copies, while the other did not.

In 2010, Victor Caston passed away at the age of 63. Later that year, so did his son Trevor "Kay-Tone" Caston, who succumbed to asthma. Lil Herb was 13 years old.

This history doesn't predict fame and fortune for Herb any more than the elder Castons could guarantee success for Kay-Tone. Nor does Mikkey Halsted's enthusiastic cosign. Herb is, after all, an 18-year-old kid, one whose past is especially troubled. Whose feet are still planted in the street, and whose future is far from ordained. On Welcome to Fazoland, the sonic palette is broadened, expanding to incorporate the Kanye-style soul of Brian "All Day" Miller's "Fight or Flight," and the ribbon of strings on the C-Sick-produced "Momma I'm Sorry." Titanic drill beats still—thankfully—make up the meat of the album's sound, granting the album a contemporary vitality. But in Herb's latest work, cracks of light are beginning to break through its darkened world.

Where some rap heads might see Herb's rap style as interesting primarily for its regionally-rooted fast rap style, for Herb, progression is about broadening his fanbase. Where some of Herb's earliest verses had a twitchy, scattershot quality, his partnership with Mikkey has provided some dividends in the studio. "My first couple of raps you can tell I hit a fast tempo, but I can rap slow too," he says. "And I just got better at it, so now it’s just second nature." On certain cuts, he still sounds as if he's ready to break into a flurry of densely packed syllables, to let his ideas get ahead of his delivery, and our ears. But Welcome to Fazoland finds his words becoming more centered on the track, his ideas coming into focus. And this, in turn, sounds similar to what working with Mikkey did for Lil Wayne in the era of the Sqad Up tapes. 

Not to put even more history over Herb's head. He's not the next Lil Wayne; he's also not Mikkey Halsted, or Kay-Tone. But he is working at reaching outside of his block. 

It's also clear his ancestors are on his mind. His latest single includes the chorus, "I'm koolin in this hellhole." It's not just a figure of speech; D 2 Tha S's first single, recorded by the Legendary Traxster and his uncle Kay-Tone in 1993, was a 12" called "Hellhole." Kay-Tone didn't find popular success living in a hellhole. Perhaps "Koolin'" in one is the answer.

RELATED: Stream Lil Herb's New Mixtape "Welcome To Fazoland"

Latest in Music