Rising Chicago Rappers You Need to Know
From Calboy to Ajani Jones, there is a new wave of artists bringing fresh energy to the Windy City. These 13 rappers should be on your radar.
Image via Sho Hanafusa/Complex Original
The sounds and flows of Chicago migrate across the city and out to the rest of the world. In recent years, Brooklyn has picked up drill music from rappers like Chief Keef and Lil Durk, and the aesthetic of R&B across the country pulls from producers like the Social Experiment and Phoelix. Now, Chicago is experiencing a new wave of talent, a generation removed from projects like Chance the Rapper’s Acid Rap. We have put together a list of the best rappers on the come-up, artists that might not be on your radar but deserve your attention. There are street crooners, brash bosses, storytellers, and crate diggers, all in one city. Some of these artists have been putting out projects for years, while others are still working on their debuts, but they’re all planting their flags in new places on the rapidly expanding map of Chicago hip-hop.
Calboy
Calboy's “authentic, soulful, catchy, emotional” sound is spreading through the city, and he knows it. “Out of the new wave, I’m the first one to come up with a platinum plaque, so I feel like I’m one of the frontrunners,” he says. Calboy earned the plaque for “Envy Me,” a portrait of his youth in the south suburb of Calumet City. “I was fighting some demons, in the field bitch I'm deep in/I was raised in the deep end, I know n****s be sinking,” he raps as his pitch arcs higher and higher with the triplets. His debut album, Wildboy, features Young Thug, Meek Mill, and local legend Lil Durk on triumphant posse cut “Chariot.” “It gave me a push to go hard because everybody is watching me now and they’re raising the bar,” the 20-year-old says. His tour with 21 Savage starts this month, including a stop at his hometown's biggest festival, Lollapalooza.
Femdot
“I could tell my story over anything,” Femdot says. “I would consider myself a multidimensional storyteller.” Born in Evanston, a college town immediately north of the city proper, Fem was a regular at open mics, eventually putting his collegiate health science studies on hold to pursue music. On “Snow In July,” a standout from last year's Delacreme 2, he narrates his struggles, waiting for the sun to come out. “Up late I was tryna be the GOAT so I don't got no time to count sheep/Stomach empty on a full mattress, all I had to eat was sleep.” Fem kicked off a weekly release series called #transmissiontuesdays with a new single “Whole Thang,” and he has a new project out later this year. He includes local legends like Twista, Bump J, and Lupe Fiasco in his list of storytelling inspirations, and he's excited to see a new wave of Chicago artists come up together. “We're tired of watching people pass us when we know we have the talent and the ability to get there.”
Chris Crack
“I always tell ’em it's some playa shit,” Chris Crack says of his free associative sound. Originally from the West Side neighborhood Austin, Crack has been steadily releasing music since 2012, including collaborations with foils Vic Spencer and Tree. But he’s become especially prolific recently, dropping four projects in the second half of 2018 and three so far this year. “I like the idea of like, you’ve gotta catch up with me,” he says. “There will never be a time when you’d be like, ‘Man, Chris Crack ain't go no new shit?’” Each project features songs with short runtimes and non sequitur titles like “Michael Jordan Don't Leave Comments” and “Pimp Hand Level One.” “Twist out a baggie, call me daddy, ask the baddies what they want/Phoning home plenty, that's on henny, never eat at Denny's,” he raps on the latter. Crack seeks out music in foreign genres and languages, like the Korean soul tracks he’s recently used as sample fodder. “Music is universal,” he says. “You don't know what they be saying, but you get it.” With his wide-ranging sonic palette and an exaggerated rap voice that renders every bar in comic book speech bubbles, it’s fitting that he’s been teasing a collaboration with Madlib coming soon. He also has another project on the way, dropping on his birthday, July 31st. Time to get caught up.
Ric Wilson
“If Curtis Mayfield came out rapping, he’d sound like this,” Ric Wilson says of his take on hip-hop that mixes disco and funk influences into an irresistible concoction that will push you to dance. On “Split,” wobbling bass and clattering percussion build a groove as Wilson rhymes about indecision: “Stuck between caring too much and giving up/Victim of tweeting but not reading enough.” The Blue Island native credits Chicago’s scene for honing his live chops. “Being able to be a live performer is a thing out here in Chicago,” he says. “You go to any other city, and everybody can’t perform. Wilson has been balancing band rehearsals with recording sessions alongside other musicians across genres, part of collaborations he attributes to his “Prince period.” Catch the next project from Ric Wilson this fall.
Supa Bwe
Supa Bwe was wailing with pop-punk energy before Uzi ever went on tour with XO, but his style extends far beyond that. “It’s like a fucking charcuterie plate,” he says. “Good ass meat, good ass cheese, nothing but content.” He adds, “I’m a new age Renaissance man.” Supa was a part of Chicago's last big wave as part of trio Hurt Everybody, when artists like Chance The Rapper and Mick Jenkins first hit the national stage, and now he wants to provide for the next generation. “If we just eat all the apples and don’t leave no seeds in the ground, the forest won’t grow. The forest gets weaker every season, and that’s how Chicago remains a secondary city.” He's dropping an EP called Jaguar next month, and the title was inspired by white police officers who recently accosted him outside of a friend's home recently, fearful like they were facing a wild animal. But with the whole project produced and engineered at his home studio, Supa Bwe is also showing that this is his forest, and he’s ready to eat.
Queen Key
Queen Key is not subtle. On her single “My Way,” she raps, “I'm a spoiled ass bitch, I get what I wish/If that n***a got a problem, he can suck his own dick.” The Blue Island rapper refuses to cede an inch of control to anyone else, making her a tenacious role model for fans. “That's why I'm so welcoming to my fans, because it's like I understand them,” she told The TRiiBE last year. “I see me when I see them because I am a little black girl. I was a little black girl.” Queen Key prefers beats that boom like her authoritative bars, such as the distorted explosions on the ChaseTheMoney-produced “Ratchett.” After dropping her debut mixtape Eat My Pussy last year, she followed up with her second in May, titled Eat My Pussy Again. Don’t make her say it a third time.
Polo G
“I want people to consider me potentially one of the best artists to ever do it,” Polo G says. So he takes his time with his music: “I don’t want to put out no BS and I’m not freestyling in the stu. I want everything to be well thought out.” His breakout single with Lil Tjay, “Pop Out,” is a menacing anthem, warning others to “tuck your chain” when Polo crashes your party. The track’s infectious hook propelled the song to No. 11 on Billboard’s Hot 100 chart earlier this summer. The North Side rapper's debut, Die A Legend, debuted to debut at No. 6, and he is hyped to see other Chicago artists find success, too. “I support every single artist from the city because we all coming from the same demographic, whether you from the west, east, south side of town, we all going through the same stuff on a day-to-day basis, so I just love to see artists from Chicago come up and do their thing,” he says. Polo is working on a follow-up to drop this winter. “I’m already ready to outdo my last couple achievements,” he says. Polo G’s next milestone: a national Die A Legend tour starting next month.
Lil Zay Osama
“I probably got the realest music in Chicago right now,” Lil Zay Osama says. The rapper grew up in Bronzeville’s Robert Taylor Homes, moving to Englewood with his family after the projects were demolished, and he has turned his years in the streets into Auto-Tune’d anthems of success and betrayal. On recent single, “Back When I Was Young,” he compares his youth, growing up stealing cars and ditching them before the police arrive, to his present, rocking Amiri jeans and making press appearances at BET. Lil Zay Osama’s forthcoming debut project will be called The Hood Bible because it’s like “I'm preaching to the streets,” he says. But that doesn’t limit his melodic music’s appeal. “You’ve got people that hate me, and you’ve got people that love me,” he says. “But the people that hate me, they know that I speak real music, and everybody can relate.”
Joseph Chilliams
Joseph Chilliams is one of the funniest rappers in Chicago. He’s a member of West Side group Pivot Gang along with his brother Saba, and he drops quotables all over their recent album You Can't Sit With Us: “Keep my circle tight like new braces,” “Like Sammy Sosa, I know that I blacked in my past,” and “Sit that ass on my face ’til I look like an orangutan.” (He’s also the group's most enthusiastic dancer.) Chilliams dropped an EP last year called The Plastics, taking inspiration from millennial touchstone Mean Girls the way coke rappers pull from Scarface. But he’s not some Buzzfeedcore nostalgia machine; Chilliams wrings real pathos out of his characters. With a new solo album in the works, catch Chilliams gyrating across your local stage soon.
Taylor Bennett
On his new album, The American Reject, Taylor Bennett raps about the perils of blowing up on “Streaming Services” and pays homage to the mother of his children on “No One Outside,” augmenting his bars with pop-punk melodies inspired by Plain White T’s and the All-American Rejects. Growing up in Chatham, he first knew he wanted to rap after hearing Twista and Faith Evans’ collaboration “Hope.” “It inspired me to say I want to help people with words, and I love how that song changed my perspective on life and what I could do at such a young age,” he says. Bennett explained that he wants to make timeless music: the kind of songs that get played at weddings and funerals. His lush live band has garnered him performance slots on Kimmel, at Taste of Chicago opening for De La Soul, at Complexcon, and a still-to-be-announced support slot on tour with a major artist. Bennett is excited that he and his peers are continuing to build out the music industry in Chicago: “We are acquiring a new blueprint to make somebody actually successful, and I think that’s not going on anywhere else besides Chicago, because we don’t have independent artists like that anywhere else.”
El Hitta
On his breakout hit, “Aww Yea,” El Hitta bellows through Auto-Tune over piano, like if Future ever went outside in the daytime. “Brains on his shirt, he a stain/Thought we had a bond like James,” he raps. Hitta was inspired by G Herbo's “humble energy” growing up, and that apparent contradiction runs through his boisterous yet reflective tracks. “I really been through the struggle, and it’s like you can hear me crying out in my music,” he says. The Humboldt Park native is proud of the current scene in Chicago: “Even if I don’t wanna do a song with you, I’m still gonna have respect for a person that came from the bottom as well.” Hitta’s next project, Proved Em Wrong, is coming later this year, though he is considering dropping a mixtape first to build hype even further. And he”s setting his sights high for dream collaborators. “Bruno Mars,” he says. “I just feel it.”
Ruby Watson
Ruby Watson makes weirdo rap. “Definitely weird and glitchy and uncomfortable, but it’s personal and genuine at the same time,” the Kansas City transplant says. His self-produced debut album, Balance, is about dodging depression and addiction through community, when buying a junker is a small victory that means freedom from public transit and a new place to hotbox with the homies. Ruby’s beats build on dusty samples, distorted vocals, and warm keys, a potent stew for anyone who grew up digging through DOOM and Earl rarities on YouTube. Along with fellow rappers Malci, Davis, and Joshua Virtue, Ruby launched an independent label, Why? Records, to release their projects, as well as tapes from duos UDABABY (Virtue and Davis) and Free Snacks (Watson and Virtue). For a rapper who spit “property is theft” at the end of a verse like a mic drop, it’s fitting he’s dismayed at Chicago artists only chasing the bag. “If motherfuckers really want to see their scene shine, you have to start with your community and those who are creating for their community,” he says. “That’s where genuine, interesting, and provocative art comes from in my opinion.” After completing another Free Snacks project, Ruby and Joshua hit the road with Malci this September for an East Coast tour.
Ajani Jones
“When you hear me, I want it to be a special occasion,” Ajani Jones says. That determination is a key part of his story; the South Side rapper left a full-ride scholarship studying psychology at the University of Iowa to return to Chicago and refine his music through open mics. His debut album, Dragonfly, showcases him rapping over a range of rhythms held together by an undercurrent of neo-soul: music he grew up hearing on his mom's stereo, mixed in with 50 Cent and Ludacris. “It's rooted in a melodic tone that goes back to Lauryn Hill, Floetry, a little bit of Musiq Soulchild, and I mix it with the nuances of modern hip-hop,” Jones says. He’s ready to follow in the path of Chicagoans like Noname and Saba and build his own legacy at home. “Chicago is looking for that next class,” he says. “It's given us an opportunity to build on what they did for us.”
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