Best Music Scenes 2020: Chicago - Rolling Stone
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Inside Chicago’s Wild Music Scene, From Trailblazing Hip-Hop to Indie Jazz

The Windy City is one of the most adventurous, experimental scenes in the country — here’s why

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Photograph by Aaron Engler

Aaron Engler

In our new series, we look at eight cities where live music has exploded — from legendary hubs like New Orleans and Nashville, to rising hot spots like Tulsa, Oklahoma, and Portland, Maine. The latest? Chicago, where artists are pushing the envelope at secret clubs, strip clubs and more.

Chicago has always been a city for musical risk-taking. It’s where the Chess brothers helped introduce electric blues to the world and Kanye West changed rap 50 years later. Today, it’s home to one of the most adventurous, experimental scenes in the country. Just take a visit to the Silver Room Sound System Block Party, where veteran house DJs share billing with outré hip-hop and jazz ensembles. Fueled by strong indie labels like International Anthem and FPE, the city is experiencing a major jazz renaissance; Makaya McCraven, Angel Bat Dawid, and Nicole Mitchell are connecting Chicago’s long history of avant-garde innovation with inspirations ranging from hip-hop beats to Nineties post-rock.

An exciting new hip-hop sound has emerged too, thanks to up-and-comers like Calboy, Polo G, and Lil Zay Osama, who have softened some of drill’s hard edges, pairing deeply honest lyrics with delicate melodies over lilting beats. “It’s the launching pad,” says Merk Murphy, co-founder of the city’s Complex 2010 studios (an epicenter of drill music) and co-manager of key export Chief Keef. “It’s like a treasure hunt of sorts — by the time you find out about them, they’re already almost gone.”

Street Soul

Calboy, 20, became a surprise national success in 2019 with his melancholy ballad “Envy Me,” which helped win him a deal with Meek Mill’s Dream Chasers Records. But as he steps onto the national stage, Calboy remains focused on repping his hometown, even while trying to push hip-hop in new directions. “I feel like we’re just gonna move a little different, a little smarter,” he says. “We’re drifting away from the streets, staying out of that life.”

Garage Heroes

Twin Peaks, with their approachable garage-pop sound and sunny psychedelic vibe, are pillars of the local indie scene. (Start with their 2014 breakthrough LP, Wild Onion, then head next to 2019’s Lookout Low.) Among their fans: indie-rock elder statesman Stephen Malkmus, who pronounced Twin Peaks “fuckin’ rad” in 2015.

Secret Rap Shows

New rap artists can often be found performing at strip clubs in the city’s southern suburbs, like Red Diamond (Megan Thee Stallion performed there last year). Elsewhere, 606 Open Mic Hip Hop has taken over Subterranean — one of the few nightclubs that routinely books rappers — regularly for the past two decades. And Jam Night, led by Stix, a drummer who has worked with Chance the Rapper, among others, is a monthly hip-hop and R&B party with a live band that rotates from venue to venue. Chance has been known to stop by. “I wanted to create a space where musicians can go create and be vulnerable,” says Stix. “One night can be more rock, one can be more R&B — it’s an actual jam, where whoever’s in the room creates the vibe.”

The Future of Jazz

Dorian’s Through the Record Shop is a speakeasy located, as the name suggests, in the back of a record store. There’s a casual atmosphere, but never a dearth of great music — recent performers include up-and-coming saxophonist Isaiah Collier and local-legend guitarist George Freeman, who is 92 years old. “It’s not the kind of jazz club where you feel like you can’t talk,” says International Anthem co-founder Scott McNiece. “More of a good time — the kind of place you can invite your friends.”

Far-Out Sounds

On the South Side, the AACM Great Black Music Ensemble perform on the first Sunday of every month at the Stony Island Arts Bank. The group, connected to a long-running collective devoted to experimental takes on black music, finds ways to push reggae and African sounds forward each week. On the North Side, try the Green Mill, particularly its Sunday-night sets with the Joel Paterson organ trio. “It’s one of my favorite clubs in the city,” says McCraven of the century-old spot where Al Capone was once a regular.


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