Chicago hip-hop is closing out its biggest decade on the international stage with some remarkable releases and dramatic moves on the charts. Yet the mainstream press has rarely reflected the reality on the ground here, instead focusing on obviously popular figures such as Chance the Rapper and Kanye West (both of whom dropped albums this year that I’ve mostly forgotten). And though the media finally caught up with Juice Wrld as soon as his second album, Death Race for Love, debuted atop the Billboard 200, I saw far more coverage of his unexpected death earlier this month (and of the still-emerging details surrounding his run-in with the feds in the last moments of his life) than of his music.

Of course, it’d be unfair to make these complaints about the state of music reporting and criticism without acknowledging that those fields have been disproportionately harmed by the instability in the journalism business. News and culture outlets continue to shut down at an alarming pace (pour one out for Pacific Standard), and at those that survive, music coverage gets cut before hard news does as budgets shrink. (The situation is even worse for people trying to write about theater, dance, books, or visual art.) This is by no means a new trend—the Sun-Times hasn’t had a full-time music critic for years—but it does make it increasingly difficult for curious fans to get a sense of what’s happening in their regional scenes. When one of the most aggressively visible Chicago rappers of the decade, Vic Mensa, pulled a Tommy Wiseau in August with the political rap-rock album 93Punx, Anthony Fantano of the Needle Drop (who’s based in Connecticut) was the only noteworthy critic who bothered with a review.

A note for those who may have forgotten: Chance the Rapper has only updated the Chicagoist homepage once since publicly announcing he’d bought the defunct news site in July 2018: he added a “find your alderman” search that became inaccurate when the newest batch was inaugurated in May. In November, Chance told Fast Company that he plans to relaunch “the Chicagoist” as an app devoted to food and entertainment, then cede control to an editor. But unless Chance also sells the app, one of the city’s few outlets focusing on local music will be owned by its biggest pop star.

For six years now, I’ve put together an annual list of the best overlooked hip-hop releases in Chicago. Under present circumstances, determining what counts as “overlooked” is more challenging than ever—fewer and fewer releases get any media coverage at all. That’s just one variable that goes into my decision, though: I also consider chart placements, streaming stats, frequency of local performances, accessibility of the music to fans, social media presence, and more. Because I regularly cover Chicago hip-hop, I didn’t include any artist I’ve ever written about before—but that still left me with more candidates than I knew what to do with.


Jim Crow: The Musical

Veteran rapper Add-2, who also mentors at-risk youth via programs at his Haven Studios, unpacks the complexities of Black life and Black art as well as the deep historical roots of structural racism atop white-knuckle beats and sumptuous soul melodies.

Don’t Be Kendall

Did U Die?

Don’t Be Kendall distills youthful vigor into loose lines that he sprays across stylistically disparate instrumentals—and he’s got the charm to make it all hang together.


Rambe World

Kahrion has a husky voice and the lyrical perspective of someone who’s seen it all, and on Rambe World he wisely uses gritty old-school beats to complement his stylish air of mystery and magnetic mystique.

Ness Heads


On her debut EP, Numb, Ness Heads flips between lightning-fast rapping and cool-in-the-pocket singing with enough grace to make you wish stardom were a meritocracy.

SBG Kemo and Shawno

Kollege Kidz

Rising street rapper SBG Kemo brings along his friend Shawno for a smattering of frenzied tracks that sparkle with a smidgen of pop glee despite the hard edge in the duo’s delivery.

Honorable mentions

Escher, Escher

Illuminati Congo, Time Killaz

Malveaux Donnell, Memoirs 7

Noah., What Was That?

Semiratruth, I Don’t Wanna Have to Yell for You to Listen  v