62 ` Rolling Stone ` February 2020
The Windy City is
currently home to
the most innovative
hip-hop scene in
America — and jazz
is being reinvented in
wildly psychedelic
new ways
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
C
HICAGO HAS ALWAYS been a city
for musical risk-taking. It’s where
the Chess brothers helped intro-
duce electric blues to the world
and Kanye West changed rap 50 years later.
Today, it’s home to one of the most adventur-
ous, 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 con-
necting Chicago’s long history of avant-garde
innovation with inspirations ranging from
hip-hop beats to Nineties post-rock. An
In the past five
years, Bad Bunny,
Luis Fonsi, and
Daddy Yankee
have helped make
Latin music the
fastest-growing
genre in the
world. They all
have something
in common: They
all have roots in
San Juan, which,
despite its small
size and economic
struggles after
Hurricane Maria,
has become a
world-shaping
music scene, with
forward-looking
salsa, reggaeton,
bomba, Latin trap,
and more. “It can
compete head-to-
head with other
Latin American or
European cities
because of its
diversity,” says
Bárbara Abadía-
Rexach, a Uni-
versity of Puerto
Rico anthropology
professor. To get a
picture of the rich
scene, head to La
Placita, a market-
place that turns
into a giant musi-
cal bash at night,
with more than 15
bars. At the hip La
Respuesta, you
can pay $10 and
see anyone from
local indie-pop he-
roes Los Wálters
to jazz trail blazer
Miguel Zenón.
One of the scene’s
biggest moments
will happen in
May, when Bad
Bunny returns
for a two-night
stadium blowout,
which may break
Metallica’s ticket
sales record.
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Chicago,
Illinois
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 differ-
ent, 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 perform-
ing at strip clubs in the city’s southern sub-
urbs, like Red Diamond (Megan Thee Stallion
performed there last year). Elsewhere, 606
Open Mic Hip Hop has taken over Subterra-
nean — 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 col-
lective 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. NATALIE WEINER
PRAISE YOU Clockwise from top:
Chance the Rapper; Post Animal’s
Jake Hirshland and Twin Peaks’ Cadien
Lake James (right) at a favorite Lake
Michigan swim spot; a Red Hot Ranch
burger; Twin Peaks at Thalia Hall
After-Show Stops
RED HOT RANCH
The hot dogs at this local chain, a
popular spot for musicians, are a must.
FREEHAND CHICAGO
This hotel is worth a stay for its
top-notch selection of lobby DJs.
HOT
DESTINATION
SAN
JUAN,
PUERTO
RICO