In the 2010’s, drill music’s tough-as-nails bars and sinister beats were a Chicago hip-hop hallmark. The lyrics painted a dark picture of life on the streets for Chi-town’s urban artists, often violent and nihilistic. In the 2020’s, Chicago’s drill scene descendants are expanding on that theme.
Hardcore themes of betrayal, survival, and death remain, but the music behind the lyrics has turned hauntingly lovely. Plaintive guitar riffs, poignant piano runs, and nostalgic samples illustrate the bitterness of betrayal and loss or stress the importance of solidarity.
Chicago’s hip hop artists in 2021 are breathing fresh energy into the Windy City. If you love no-holds-barred hip hop, these ten should should definitely be on your radar.
Pinqy Ring
International performer and Chicagoland native Pinqy Ring’s breathtakingly courageous projects confront a different type of trauma than most Chicago hip-hop. Powerful authenticity, witty word-play, and Latina flavor deeply connects with listeners and encourages personal empowerment. This is real music, and she’s sharing it with the whole world, from Chicago to Belgium and beyond.
TrenchMobb
This young mixed-ethnic group from the West Side set Chicago buzzing back in 2018. Led by JR007, TrenchMobb consistently premiers new material featuring JR007’s fast-talking hooks and TMB Spazz’s flex-heavy, AutoTuned rhymes. Complementary styles give TrenchMobb an electric chemistry ready to sizzle in 2021.
Lil Durk
Lil Durk was a key figure in Chicago hip-hop’s early drill scene. Over the past decade he’s blossomed as a melodic trap music innovator, and he’s finally receiving hard-won props. Last summer’s “Laugh Now Cry Later” collab with mega star Drake catapulted Durk into the mainstream. Lil Durk enters 2021 with his first Billboard No. 1 album, The Voice.
G Herbo
Platinum-selling artist G Herbo’s music reflects life in the South Side neighborhood known as “Terror Town.” He made Forbes’ 30 under 30 list for 2021 and performed “PTSD” ft. Chance the Rapper on The Tonight Show – a somber tribute to fallen emo-rapper Juice WRLD. Herbo responds to recent fraud charges in his newest release, “Statement.”
Queen Key
New mama and future GOAT Queen Key is a force to be reckoned with. Even after giving birth to TRIPLETS in 2020, this Blue Island native has been pushing out new singles plus episodes for her YouTube vlog Key + 3. Queen Key opts for booming beats backed by bawdy bars, like the distorted bass on “Ratchett.” Don’t sleep on this brilliance. With her bold ambition, this Queen is poised for a hot year.
Lil Zay Osama
One of Chicago’s hottest hip-hop artists, 23 year old Lil Zay Osama’s “Changed Up” went viral two years ago, garnering 12 million views in one month. Going into 2021, his rising star continues to shine. Marked by heavy AutoTune, Zay’s compelling music and visuals permeate his body of work. Lil Zay’s ability to turn tragedies into triumphs is a true talent, so watch for more stellar releases in 2021.
Joseph Chilliams
For a punnier Second City twist, blaze up and cue Joseph Chilliams on the big screen. From Chilliams’ Napoleon Dynamite spoof in “Fergie” to his latest holiday single, “Wishlist,” you’re gonna want to “Taste it, taste it.” Last year’s projects were mostly focused on dropping bars with West Side group Pivot Gang, which is badass, but here’s to more foolery in 2021.
Calboy
2020 XXL Freshman Calboy rose to recognition after his 2018 single “Envy Me” blew up on YouTube two years ago. A prolific writer boasting a slew of collaborations with artists Polo G, Moneybagg Yo, Lil Durk, Meek Mill, Young Thug, G Herbo, Chance The Rapper, King Von, Lil Baby, and more, Calboy is set to pop off even harder throughout 2021.
Polo G
Chicago hip hop rapper Polo G landed the top spot on Rolling Stone’s “20 Best Hip Hop Albums of 2019” as, “The emerging leader of a new class of rappers from the city.” An XXL Magazine 2020 Freshman of the year, Polo’s deft delivery, knack for beats, and spontaneous veracity has snagged him recent spots on The Tonight Show Starring Jimmy Fallon and NPR Music’s Tiny Desk Concerts. This one’s ’bout to be a GOAT.
Chance The Rapper
Love him or hate him, Chance the Rapper is back, featuring a string of virtual concerts and new singles reminiscent of favorite mixtapes like Coloring Book. 2020’s acid rap-laced single “The Return,” a Bieber collab, and The Tonight Show appearance with G Herbo resurrected the rapper’s defunct career. And he’s charging 2021 with an upcoming Dionne Warwick collaboration to support Chance’s Chicago-based nonprofit, Social Works.
This list of Chicago’s best hip-hop artists in 2021 is by no means exhaustive, and it was really tough picking our top ten. Cheers to all the rappers, singers, songwriters, and producers heating up Chicago’s music scene in 2021.
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