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Eagle is a son of the now-demolished Robert Taylor Homes in Chicago, and fluctuated around the Southside through his adulthood. He kicked his first rap in the back of a KFC in Hyde Park, but he prefers the Harold’s Chicken on 53rd. Leon’s BBQ on 79th and Stoney holds a special place in his arteries as well. He first moved to L.A. in 2004 to serve Dorsey High School in South L.A. through AmeriCorps VISTA: a government-subsidized volunteer program bringing tutoring and after-school support to underserved youth while placing its workers at poverty-level themselves. Even in 2004, the wage was unsustainable for L.A.; after nine months in the trenches, he worked several other jobs in schools and halfway homes while finding a home in Project Blowed and jumpstarting his career via the group Thirsty Fish with Dumbfoundead and Psychosiz.

Eagle’s first solo album Unapologetic Art Rap arrived with a whimper in 2010, but led the charge in defining the “art rap” niche at a time when gangsta rap aesthetics still dominated the mainstream, and a select few began the march into rap’s odder possibilities. He didn’t coin the phrase — his contemporaries Busdriver, Serengeti and more were using it before — but Eagle found a strong necessity to expand the idea and self-determine the context. Unapologetic Art Rap sets the tone for the off-kilter progressiveness of the Open Mike Eagle oeuvre: a boom-bap foundation dressed in odd electronic trinkets and blips, the grooves churning along to pad the intense multi-layered lyrical technicality that requires as much skill to execute as it does to process as a listener. It’s gleefully weird, Black and nerdy all together without apology. But according to Eagle, the term art rap is no longer necessary: When you can dig the deep net for any kind of rap you want, its connotation now shifts to a discussion of which resources were available to the artists you’re listening to.

“It’s not to say that anybody’s lesser than because they’re in a good economic situation,” Eagle says. “The reason to have labels: it’s helpful for us to explain to consumers the differences in how this product arrived to them, because there’s a tendency to put it all in the same sentence, which is cool! In one sense, you have a seat at the table, which is great, right? But in another sense: you don’t necessarily want your work to be compared to somebody who has hella more resources, or at least you want that to be part of the conversation. If you’re scratching and clawing to survive, I feel like that should be part of the conversation in assessing your work. Even if that’s a choice, that should be part of the discussion.”

But what does one make of the underground today? With a supposedly infinite accessibility, and a similar chorus of hands on the strings of what rap rises to the top, what does underground even mean? Flashback to the Mike Eagle who bust his first rhyme in the KFC, the same man who used to go to The Point to immerse himself in the founding elements and principles of hip-hop. Think of him as a child, tuned into the radio, fingering through bootlegs in the sleeves of a CD jacket or the stores of a local library. Where are folks like him born and bred to carry this tradition forward? While the way’s been paved for a milo, a Sammus, a Quelle Chris to thrive in the fringes of the rap we’re presented on a mainstream level, which folks are seeking the art of Black folks — for Black folks — outside the margins of our sponsored, playlisted reality?

Recalling his time at Dorsey, his observations are streaked with confusion and an air of sadness: the fists on the lunch tables and locker doors of his youth may be far gone. And the Black kids of that time that closest resembled the Mike Eagle of his time — emo kids, gamers, art nerds — fed their inner outsiders without hip-hop to guide the way.

“I think of all trajectories, that was the one that was most surprising to me,” Eagle says. “I figured that would’ve grown, but it didn’t, it just kinda went away. Instead of these kids thinking that there was anything they could relate to about hip-hop, they were relating to [emo and pop-punk.] I guess what bothered me about it is that shit was marketed to ’em; it wasn’t like ‘Oh, these kids just found this music they like a lot!’ No, this was the stuff that’s signal-boosted for these lonely kids! They weren’t seeing anybody inside of hip-hop who were relatable to them.”

Open Mike Eagle is made for kids like them, but Open Mike Eagle isn’t streamlined to them. “Story of my career,” he posits, sipping the literal tea in his hand. Eagle notes the success of his fantastic Brick Body Kids Still Daydream release as another artistic milestone; every time he drops a new project, more young Black folks are paying attention to him. But even he’s unsure of the machinery that’s aiding his trajectory, and he’s surely skeptical of any system improving or opening up for folks like him to prosper. When he considers where he fits in the Spotify algorithm, for example, he’s in the same pool as his contemporaries — many of whom he’s worked with — but virtually no one else beyond those layers, sectioned off into the art rap echo chamber. While he’s made big playlists and received bigger streaming looks as his profile elevates, it begs the question of which bits of code are drawing the lines that are further containing folks who create under a certain context while minimizing the crossover potential.

“I feel like there’s a line from J. Cole to me,” Eagle wonders. “Not an exact line, but if you’re gonna list 10 related artists, I feel like I could be nine or 10!”

But Mike Eagle’s hustle is never contained: He’s dwelled in everyman territory far before it became the millennial default, the fortitude only chiseled from a long tenure navigating independent artistry. He hosted the Secret Skin podcast to interview other MCs on life and craft, captained countless U.S. and overseas tours with small crews helming the whole operation, made his feature-length film debut in this year’s It’s a Party and recently pivoted his L.A. comedy residency The New Negroes, in collaboration with Baron Vaughn, into a Comedy Central series currently in production. The latter is the reason why Eagle’s phone won’t stop buzzing through the interview, and he’s brimming with excitement through the tired exterior. Without giving anything away, he champions the music that’s coming with the show and smirks when detailing the “crazy-ass guest stars that we were able to talk into doing a buncha crazy shit!” If all goes well, the Open Mike Eagle brand’s poised to take off even further into the unfathomable artistic ether with no shortcuts and no extra hands tying his own.

It’s only fitting to remember Unapologetic Art Rap as a stepping stone for the Open Mike Eagle we know today. (He had another album done before it to press on a smaller label, but it sounded terrible.) Released on Mush Records, home of early releases from the likes of Daedalus and Busdriver, the success of his group Thirsty Fish gave Mush enough room to drop the first Open Mike Eagle album as a side project. Eagle trusted the release process to them while dreaming of a new tomorrow, a now-laughable delusion in the tradition of any rapper putting out their first album. He recorded it all in his office home studio with a growing sense of studio technique, projecting low and close into the mic, every mix saved by the engineer. The bars were landlocked into strategic multi-rhyming grids with a theory wedged in; a brainiac’s pen, running the same trick constantly and trying to outrap everyone. Half-baked as it was, it proved Open Mike Eagle could finish his ideas.

“I didn’t know nothin’, man,” Eagle remembers. “I just completely trusted that they were gonna take care of everything. I had a lotta delusions at that time: I was teaching then, and I can remember this one day where I faked like I had to go to the bathroom so I could hear a message [the label] left — ‘Oh, the album’s ready, we have a release date in mind…’ — and I came out that bathroom thinkin’, ‘Oh, these people ’round here cain’t tell me shit! Man, they don’t even know!’ I was feelin’ myself so hard! But I just had no idea how my album comin’ out — the position it was in, and even the product itself — it couldn’t have been more than a fart in the wind. The system of that label, my product, where that label currently was in the culture of the music industry, me comin’ literally outta nowhere… everything that went well about that record was just great fortune.”

In 2010, when The Throne was still together, pointing toward the museum and fornicating on the Warhols, Eagle deemed it necessary to set the context away from the High Art Pop Culture. He dwelled in the weirder territories, the basement beneath the mansion, where folks like Shabazz Palaces and Danny Brown were thriving by burning the envelope. Dropping a first album at 29 made Eagle the prime candidate for a calculated risk: full of life experiences, fantastic organizational skills and proficiency in sending a decent e-mail. And with features from the Swim Team, Busdriver, Serengeti and Nocando to help the record along, it did better than it should’ve for a relative nobody in Eagle’s position.

Today, the growth of yesteryear revoked Eagle’s delusions and made him the practical man that can run every facet of an indie rapper operation. The shows remain cozy, a few hundred fans at a time, but they know whom they’re supporting and how small the supply chain truly is. They come ready to spend on vinyl, sweaters, collectible socks; no matter the niche, Eagle supplies the demand by giving his supporters ample opportunities to do just that. He credits his time interning for Project Blowed’s label operations to see every angle of how the business works, and pines for an apprenticeship space in the indie rap sphere where the next to embark on the journey no longer have to inherit the absence of information. When he’s off the road, he’s talking basketball with his nine-year-old son, who “raps like himself, he’s got his own style.” I recall an older freestyle where he asks the viewer for support to buy his son formula and diapers. “That seems like forever ago…” he says, looking off into the distance to cherish the memory.

As a man known for his cynical takes cast off into Twitter — surely a small help in elevating him as artist and pundit — I ask Eagle how he takes care of himself. He exhales deeply, thinking for 20 seconds before replying:

“I like to… read about how the world’s going to shit,” Eagle says. “I think it surprises people sometimes how much I actively dive into reading the news. I know it’s horrifying, but I wanna understand shit; I always wanna understand how shit came to be. And I think that helps me, you know: having all the context I could process, and trying to see all the angles. Other than that, my brain will just go crazy thinking about what could happen cuz I don’t understand what already happened.”

He knows the human brain’s no match for overload, but it doesn’t stop him from diving into decoding the usual suspects — what’s happening, how it happened, who did it, who told us, why — and feeding his perspectives back into the world no matter how contrarian or inconveniently true. Even when he doesn’t intend to start a fight, his version of the truth is sharper than most. A world-weary traveler who doesn’t unplug, he scoffs at the unhealthy tab load in my phone, keeping his own to a minimum.

It’s invigorating to imagine the 37-year-old Mike Eagle nowhere near his climax, his meteoric rise to mainstream cultural importance happening closer to midlife than most allot for entertainers, let alone Black rappers making weirdo shit for folks like them. But that very thought sparks concern when considering a man like Mike Eagle being subjected to the meme, the context collapse of his suffering and survival rendered cultural fodder to abbreviate a joke. If we’re post-art rap, who’ll be the first of that class to pivot upward into that dialogue with all the rewards and consequences imaginable? It soon becomes clear that I’m the only one focused on that in my head; Open Mike Eagle’s here to be in every way he desires, every next step what it needs to be to keep him here.

“Making psychological mountains for myself to climb… not really into that,” Eagle says. “A clutter of my own making… it’s not my hang.”