City of Win Archives - Chicago Reader

Loona Dae looks down at the camera against a backdrop of green leaves, with a long black coat draped over her shoulders and a white corset-style top

Loona Dae opens up a new world of psychedelic R&B

by Alejandro Hernandez November 30, 2023November 30, 2023

“When I started skating, I was definitely in a creative rut, and I needed to push myself in a way,” says Chicago R&B singer Loona Dae. “It’s scary to fall, but I found a lot of refuge in skating because it’s just you and the skateboard. It taught me to trust myself more and rewired […]

a black-and-white photo of Chai Tulani standing in front of a group of trees and wearing a brimmed hat and geometrically patterned poncho

City of Win

‘For me, music and spirituality are intertwined as one’

by Alejandro Hernandez October 19, 2023November 14, 2023

“Music is a spiritual thing.” These are the words of legendary Nigerian musician and activist Fela Anikulapo-Kuti, and if any artist in Chicago still carries the same pan-African spirit Fela did so many years ago, it’s Chai Tulani. Born in Kenya and raised in Chicago, Tulani has been a fixture in the city’s creative community […]

Stock Marley wears a Free Nation T-shirt in an outdoor black-and-white photo with a backdrop of tree branches

City of Win

Stock Marley invites us to show genuine love

by Alejandro Hernandez September 8, 2023October 12, 2023

“I’m not tryna get high, man. I’m tryna get righteous,” says Stock Marley. He’s in his west-side apartment, delicately rolling up a joint. “This is a daily sacrament. It’s a way of life. I’m not tryna do things fast—I’m trying to do it right. With the weed, with the music, we’re just trying to be […]

a man in jeans and an orange jacket stands in a garden plot with a large black plastic bucket

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Calez makes music his guide

by Alejandro Hernandez August 24, 2023August 24, 2023

Ten years ago, Chicago artist Calez was part of a changing of the guard in Chicago music. The south-suburban rapper made a name for himself locally during the peak of the blog era: as a member of the BRKF$T Club collective (part of a larger crew called 2008ighties), he collaborated with many future Chicago staples, […]

Galaxy Francis stands in a narrow passageway between two buildings, looking into the camera with big reflective sunglasses and one hand shading his eyes as though he's peering into the far distance

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Galaxy Francis leans into community to reinvent himself

by Alejandro Hernandez July 25, 2023July 25, 2023

Our current understanding of how galaxies form is that they’re shaped by the clumping together of dark matter, which makes up the invisible scaffolding of the universe. Clouds of gas and dust gather along this scaffolding, slowly collapsing into stars that evolve and then die in supernova explosions. These explosions create clouds of gas that […]

a triptych of rapper CantBuyDeem smoking and wearing a black T-shirt that reads "Restorative Justice Is a Lifestyle"

City of Win

CantBuyDeem to Black men: go to therapy

by Alejandro Hernandez June 28, 2023July 5, 2023

“I got all these friends but I still feel alone, imagine that,” says CantBuyDeem. These are the first words in Reality Raps, a short film created by and starring the multidisciplinary south-side artist. He’s a rapper, a model, a graphic designer, and now a filmmaker. Reality Raps, like the album of the same name that […]

Thelonious Martin sits in his blue-lit home studio in a hoody and brimmed cap, surrounded by keyboards, computers, samplers, drum machines, and monitor speakers.

City of Win

Producer Thelonious Martin keeps hip-hop’s old wisdom alive

by Alejandro Hernandez May 18, 2023July 24, 2023

Sitting under the warm blue lights of his home studio, Chicago producer Thelonious Martin reflects on his musical influences as he studies a set of shelves completely stacked with obscure vinyl. On the shelves’ top right corner rest thick biographies about two of the greatest innovators in their respective genres: jazz pianist Thelonious Monk and […]

a group of 15 people sit and stand in a posed arrangement in what looks like a lounge or even a live room in a recording studio

City of Win

TheGr8Thinkaz elevate as teachers, healers, and artists

by Alejandro Hernandez April 19, 2023June 27, 2023

It was a cloudy March day when I walked into Classick Studios to conduct my next interview for this series on Chicago artists impacting their communities. I was greeted by one of the purest forms of hip-hop: a bevy of rappers freestyling together, rhyming to the classic instrumentals of Mike Jones’s “Still Tippin’” and the […]

City of Win

Speaking purpose into artists’ lives

by Alejandro Hernandez February 9, 2023June 27, 2023

Behind a great artist, there’s often a great manager. The average fan likely never thinks about the people who manage their favorite musicians, but they’re the ones typically handling the behind-the-scenes work on the business side of the entertainment industry. Whether they’re booking performances, negotiating contracts, or just acting as voices of reason for the […]