Photo by Junny Laura
Rolling deep with the Ghetto Hipster, who is leading Chicago underground rap into a new era.
September 17, 2026
BY Millan Verma
It was nearing midnight, and about 50 yards away from us there was a man warming up on the basketball court. He wore a jumpsuit, over ear headphones, and carried himself with an air of seriousness. I suggested that he’s truly dedicated to the game, getting in extra reps late on a Saturday night. After his first shot, we had to laugh at that idea. The ball soared over the backboard then rolled onto the dark field, causing him to rummage on his hands and knees to find it. “Nah, that guy is heartbroken,” said Thirteendegrees.
We’d been loitering in Wicker Park for the past three hours, a neighborhood on Chicago’s West Side that Gen X would recognize as the set of John Cusack’s High Fidelity, and longtime readers of this website as LUCKI’s old stomping grounds. The tapped-in Zoomers, though, are sure to associate it with Thirteendegrees, the self-proclaimed “Ghetto Hipster” who is leading the way in what’s become a grey area of Chicago rap: not drill, not conscious, but the left-field underground scene that has been rather mute since Juice WRLD’s passing.
In a city as segregated as Chicago, Wicker Park is about as cosmopolitan as it gets. There’s a mix of hipsters, hypebeasts, goths, yuppies, and longtime locals; it holds an overwhelming number of thrift stores, the Supreme and Half Evil shops, and three or four small venues within walking distance. The teeth of gentrification have certainly sunk in, but not enough to rip the area’s fabric like in a Williamsburg or Silverlake. Walking around with Thirteen and his friends—Exavier, Don, and Verm, who are all involved in music or fashion—I learn that none of them live near the neighborhood. Multiple times a week they drive in from the suburbs and South Side just to post up. And, well, to work.
Photo by Exavier, shot on iPhone 5
While standing outside of Exavier’s car, he and Thirteen discussed locations to film a snippet video for “WHITE SOX CAPZ,” a standout track from his new album GHETTO HIPSTER. Filming exclusively with an iPhone 5, these grainy teasers have been the core of the album’s eight month rollout. Their goal with them, other than promoting Thirteen’s music, is to show the world how beautiful Chicago is, filming some on the lake, downtown, in Chinatown, at the Art Institute, and even inside a theatre, where Thirteen danced meekly among a sea of playgoers.
For this one, they settled on shooting outside the now-abandoned Wicker Park Bodega. After maybe thirty minutes of emoting to the song from various angles, grabbing some b-roll of street signs and passing cars, they called it a day. It was edited and posted online two days later.
When I first heard about Thirteendegrees around two years ago, the overwhelming narrative was that he sounded like early 2010s Young Thug, with a spastic and erratic elasticity to his flows that were reminiscent of the Atlanta great’s I Came From Nothing mixtapes. While the influence is clear in form, their voices are vastly different: Thug had a screeching tenor that switched octaves like an organ, whereas Thirteen sounds like there are cotton balls stuffed in his molars, giving him a more snarling nasality. While I wouldn’t classify Thirteendegrees as a solely “lyrical rapper,” his love of boom-bap shines through in his songwriting, which tends to be less off-the-cuff than his Atlanta-based peers.
In early 2025, around two years after he began rapping, Thirteendegrees’ breakout song “Da Problem Solva” went viral on TikTok and sparked a bidding war that landed him at Island Records. He was soon thrust into the toxic yet vibrant Instagram-meme-page-meets-parasocial-news-coverage ecosystem of underground rap. This boosted his name, but due to his early 2010s aesthetic, he was often accused of “nostalgia baiting,” something that has become a trend across media as a whole, and looms large in the underground (see: Nine Vicious).
The claim was warranted: stylistically, Thirteen pulls from the Rich Kidz swag-era, wearing snapbacks and oversized shorts, and the Young Thug influence is hard to deny, though he has been backing away from it lately, also citing Kanye West, Twista, and even Santigold as vital touchstones. Up until GHETTO HIPSTER, released August 21, his music was hit or miss for me. Like Thug, his voice attacks the track from a number of directions, so when paired with the maximalist production he often opted for, many of his songs sounded overcrowded. Some momentary breakthroughs kept me on the hook (“CC Choppaz,” “U DA BEST”), but GHETTO HIPSTER—his most tame and tasteful project to date—finally won me over.
Earlier in the day, Thirteen and I spoke at Classick Studios—a spot that has long served as an incubator for the city’s talent, playing a part in projects from Chance the Rapper, SZA, Smino, Ravyn Lenae, and countless others (including GHETTO HIPSTER, which was mixed there). It was a humid afternoon in late August, but he pulled up wearing all black with white sneakers and a grey trench coat. Relieved to find no cameras, he was visibly tired, and sounded like he had a cold. I soon came to realize he both speaks and raps as if his sinuses are clogged; a trait I imagine was a burden during his youth, but works to distinguish his voice in his current line of business.
Born Jalen Hughes in Chicago’s South Side, the rapper was an only child raised by three women: his mother, grandmother, and aunt. He was adjacent to the street culture that the South Side is notorious for, attending the same high school as drill rapper MAF Teeski, but focused whole-heartedly on basketball until his early 20s. From the fiercely competitive AAU circuit in middle school to getting recruited to play for the Hillcrest Hawks in high school, he was a physical guard with quick hands, precise passing, and a 40% three-point shot his senior year. In 2016, the Chicago Tribune dubbed him “Jumpin’ Jalen Hughes” after a 26-point outing. As he tells it, in high school he cared about two things: basketball, and “getting fly.”
While he didn’t consider rapping until after his basketball career ended, he was a bonafide music nerd all throughout. A SoundCloud digger during its golden age, and an absorber of his city’s ongoing breakthroughs in rap: the drill of Chief Keef, Lil Reese, Lil Durk, and Fredo, and Chicago bop from artists like Sicko Mobb and Lil Chris, whose party energy are apparent in much of his early work. It wasn’t until Thirteendegrees hit a low point that he started to make music.
While playing basketball in high school, he was fully set on continuing at a Division 1 university, but had to go to a junior college instead, which “crushed” him. After two years at Moraine Valley Community College, he moved to San Antonio to play for Our Lady of the Lake University, a small catholic school in the NAIA division. Arriving during the height of COVID in 2021, he was effectively trapped in a new school, state, and city where he knew no one. Depression ensued, and he soon stopped going to practice and school altogether.
“I was seeing my friends get drafted or playing college ball on ESPN. I feel like I failed because my family is basketball-oriented. It felt like basketball was do or die, with all the work I’d put in over the years, but at the same time, I did feel like I gave it all I got and just couldn’t do no more.”
He moved back home and swore off basketball, diving deeper into fashion instead. “I didn’t even wanna touch a ball at that point. I was taking fit pics and listening to underground music, but I didn’t see myself being a rapper.” He decided to take the leap when he saw a gaping hole in Chicago’s underground scene. “Around 2022, there wasn’t nobody you could compare to Yeat or Destroy Lonely from Chicago. I thought to myself, Shit, that’s a land I can live in…I’m always thinking about the grey area. Like, why was nobody in Chicago doing this? It’s the third biggest city in America, so if everybody gets behind me, being from here will be like a cheat code.”
Photo by Junny Laura
The theory has proven true, as Thirteen’s success sparked what’s been dubbed the #NEWCHICAGO movement, a small but rowdy scene of streetwear demons and left-field rappers. However, Chicago’s startling lack of industry infrastructure has historically kept the city’s surplus of talent from breaking out. Thirteendegrees is particularly distraught by this, wondering out loud why so many of the city’s stars move to L.A., NYC, or Atlanta, saying that even Kanye West needed someone from Brooklyn to put him on the map. He hopes to play a part in changing that, though. On “MEMBERSHIP,” a boom-bap inflected standout on GH, Thirteendegrees croons: I tell the kids in Chicago/You don’t gotta be a gangster, hello/Look at me, little n***a, and follow.
It was at this point in our conversation I realized how savvy of a tactician Thirteendegrees is. Unlike many of his underground rap peers who feign tunnel vision about the complexity of their careers, Thirteen is hyper-aware of the audiences available to him and the ecosystem he exists in. In Wicker Park, he broke down three different factions of underground rap with surgical detail, and explained where and why each of his past projects fit among them. With GH, he was taking a risk. Rather than digging deeper into the high-octane trap sound he built his initial following from, he made something more laid back, introspective, and true to himself.
“[GH] is a bridge for everything,” he said. “You can still get that Atlanta-type vibe, but you can also get this conscious-type vibe, but then also a UK-type vibe. So it’s like, what box do you put me in? Am I still part of the Atlanta underground? Is it boom-bap? Is it UK?”
In an underground rap landscape dominated by snippets and singles, it is refreshing to hear a project that contains the clarity and cohesion of GHETTO HIPSTER. The album asks a simple question: What if 2013 Young Thug hopped on the cloud rap beats of early A$AP Rocky?
The influences are unmistakable, but Thirteendegrees manages to create something fresh while wearing them proudly on his sleeve. “This is my debut album,” he said, despite the six other projects of his available on streaming. “This speaks from every side of me, it brings all of my influences together, it’s the best representation of me that I’ve made. My other projects showed a side of me, but not the full Thirteendegrees. On GHETTO HIPSTER, I got a big chain on in the club, but I’m in the corner crying.”
Much of the project’s cohesion is thanks to Gyant, an Amsterdam-based producer whose airy vocal samples are reminiscent of Clams Casino. The tempos are slower than Thirteen’s past work, allowing his hyperactive vocals and acrobatic melodies to take center stage. He especially shines on tracks like “MEMBERSHIP” and “JEUNE OG,” has his strongest hook ever on “DWNTWN LUV,” and shows real growth as a lyricist on “POETRY JAMZ” and “LYRICZ.”
After spending nearly a year making the album, and just as long promoting it multiple times per week, I asked how he feels now that it’s finally out in the world.
“I feel drained,” he said. “I know it’s gonna take time for people to get this new me. Everybody thinks I’m on some old trap, Rich Kidz type-vibe, because that was their first impression. This whole year it felt like I was handing out CDs with a cardboard sign saying, ‘I’m different now! I’m on some different shit. Look at me!’”
Photo by Junny Laura
At the end of the night, we all went to The Hat, a late night spot in Wicker Park with Chicago Dogs and other greasy, messy delicacies. A few people recognized him, but as we sat down amongst the drunk friend groups and obnoxious high schoolers, it became clear that above all, Thirteendegrees is a regular dude. Over the past few years, he has been finding his voice, and redefining who he is as a creative rather than as an athlete. GHETTO HIPSTER is the closest he’s come to making something that is uniquely his. Though he currently exists in a grey area, I can’t imagine that will be the case for long.