In 1992, a Chicago rapper named Tung Twista broke the Guinness Book of World Records for most syllables spit in under a minute. The same year, the city saw a young artist named Common Sense drop his debut album Can I Borrow a Dollar? In 1993, Chicago Tribune critic, Greg Kot observed, “Chicago’s clubs still remains hostile to rap.” 

Between 1994 and 2003, the city’s Rap movement went into overdrive, highlighted by hit singles, albums, and music labels by artists and producers such as Da Brat, Crucial Conflict, Do or Die, the Molemen, and Typical Cats. All of this was anchored by the Chicago City Council officially recognizing July as the month to appreciate Hip Hop.

2004 and 2010 marked the beginning of the next generation of Chicago Rap. Completely dominated by the names Kanye West, Twista, and Common, 2004 and 2005 would provide the world with  monstrous albums like College Dropout, Late Registration, Adrenaline Rush 2007, and Be in the first two years. The landscape began transforming. Common brought his Native Tongues’ roots and poured it over intricately laid soul samples. Kanye made young men feel okay with expressing insecurities and emotions. Lupe Fiasco forced people to ask questions about almost everything, including the way they were perceived to the way they were affected by media.

In 2012, Chicago led the nation in homicides with 506 counts, including an astounding 152 murders taking place between the beginning of June and end of August. The unrest was indicative of something indefinable. However, out of that rubble came stark acts of creativity as previously seen in New Orleans, New York, and L.A. before it. This new genre of Chicago Rap came to be called Drill, and it propelled Chicago’s declining state into the media, highlighted by artists like Chief Keef, Lil’ Reese, Young Chop, and Fredo Santana.

In response to this, a new wave of Hip Hop have become the trend, and one need not look further than Chance The Rapper’s Acid Rap, Vic Mensa’s INNANETAPE, or ThemPeople’s Smoke Break IV to see the collaborations taking place. All of this is also happening under the watchful eye of the YCA (Young Chicago Authors) group. There is a definite and palpable artistic renaissance happening in the Windy City and the Rap world may want to pay attention. With that said, here are the 10 Chicago Rappers that listeners should be on the lookout for as the second city gears up for yet another run. Happy surfing.


Age: 20
Affiliation: Pivot Gang
Most Recent Mixtape or Album: ComfortZone

“I like to think of myself as somewhere in between [Conscious Rap and Drill Rap],” Saba (born Tahj Malik Chandler) toldThe Chicago Tribune. “The only difference between me and most of the Drill rappers is perspective. They’ll talk about drug deals or something like that [in the first person]. My raps are a front porch kind of perspective.” October 15 marked the oneyear anniversary of Pivot Gang’s debut mixtape Jimmy. Since then, the intellectual emcee who graduated from high school at age 16 (with a 3.5 GPA, no less) has continued working, showing marked improvement on his solo debut tape GetComfortable in January, and following up with the widely-praised ComfortZone in July. Only after the most recent drop did the talented kid with a real ear for production start gaining significant traction outside of his home city. Standout tracks like “Butter” and “Burnout” got the ball of national attention rolling, but he is still grossly overlooked by most of the music media world. The city knows about the young West Sider—including everyone’s favorite, Chance The Rapper, who featured him on “Everybody’s Something” off of Acid Rap in 2013—and we can only hope the rest of the country catches on and gives him the respect he deserves.

Taylor Bennett

Age: 18
Affiliation: SaveMoney
Most Recent Mixtape or Album: Mainstream Music

Yes, Taylor Bennett is the younger brother of Chancelor Bennett, commonly known as Chance The Rapper. Yes, they have borderline-identical appearances and eerily similar voices. Yes, all of this makes him an easy target for, “he’s only XYZ because of his brother” talk. But, Taylor needs to be respected for his insistence on trying to create his own musicality, while so many other young rappers are so willing to copy-and-paste other artists’ blueprints. It would be all too easy to ride big bro’s coattails, and his conscientious attempt to not do so deserves acknowledgment. All of this is aptly covered in his recently dropped “HATIN’”. Some notable songs from Taylor include the energetic “Speed Racer”, the raw “Life So Tough”, and the Summer-y “New Chevy”, which features Chi-Town’s own King Louie. Having a Drill artist like Louie jump on his track demonstrates, yet again, that the neo-crop don’t see nearly as huge a divide between Chicago’s nuanced Rap genres as so many outsiders, essentially arguing for their synonymy: “Modern day Chicago Hip Hop is elevating towards something that nobody has ever seen,” the young Taylor told HipHopDx. 

Brian Fresco

Age: 19
Most Recent Release:
 SoulMoney EP

Fresco’s versatility is perhaps his greatest strength, fluidly fluctuating between soulful real talk tracks, car thumpers, and straight-up anthems. Recently, Fresco put out an EP with Chicago producer/emcee Tree that exemplifies one of the knobs that makes the Chicago Hip Hop scene so powerful: collaboration. The 19-year-old’s SaveMoney crew brings us the name of the EP, SoulMoney, a spectacular body of music that has a track for virtually every scenario. Part of what makes him such an exciting prospect is his lack of fear when it comes to taking creative risks—he refuses to put himself in a box.

“The state of Hip Hop in Chicago right now is really dope,” Fresco said. “There is so much diversity out here! Different bands and artists make up a beautiful cluster of originality and style.” I feel like Chicago is here and here to stay. The audiences that we have the ability to reach are almost limitless!” Tracks off of the EP to check out include the gem “Take a Breath,” the gritty “Rose,” and the anthem “On My Soul.” 

Sicko Mobb (Lil’ Trav & Lil’ Ceno)

Age(s): 18 & 20 (Respectively)
Most Recent Mixtape or Album: Super Saiyans Vol. 1

Lil’ Trav & Lil’ Ceno are hardly slept on: In December, they signed a publishing deal with producer Stargate’s Stellar Songs/Water Music Publishing, an imprint of Sony/ATV. On top of that, they signed an official record deal with Polo Grounds/RCA in May, which also has key A$AP Mob members Rocky and Ferg. Despite the deals — and a growing amount of press — the country is largely out of touch with Chicago’s incredibly popular Bop, the dance and accompanying music. Originating on the West Side and jettisoned into popularity by “Bop Kings” like Dlow and Kemo. Their anticipated follow-up mixtape Super Saiyans Vol. 2 is coming soon—along with an EP—according to the duo who basically started rapping as a way to give themselves a positive outlet. Sicko told HipHopDX that “the state of Hip Hop in Chicago is on the rise” and that many hometown artists are “getting attention outside of Chicago.” It’ll be interesting to see if Sicko Mobb can break into the mainstream.

Vic Spencer

Age: 32
Affiliation: Treated Crew
Most Recent Mixtape or Album: Vision Pipes

About a decade older than everyone else on this list, The Rapping Bastard takes a different perspective than most of the other artists included: “The Chicago Music Scene is whack,” Vic tells Vita 1017’s Ticara Davis. “The Chicago Rap Scene is a retarded bus with a blind person driving it. We got the most talent but the most rappers.” While these words appear unabashedly negative at first, he’s mainly blasting the copycats, a group that generally receives similar “feedback.” Regardless of his polarizing words, there is no way to misinterpret his talent. His clever wordplay and signature voice make him instantly recognizable on a track. Most recently, the hyper-confident emcee dropped “24k Visuals” exclusively on SoundCloud and announced that, in addition to the The Cost of Victory and Women’s Bathroom projects he is working on, there is also another collaboration with Tree coming to be appropriately named VicTree.

Mick Jenkins

Age: 23
Affiliation: Cinematic Music Group
Most Recent Mixtape or Album: The Water(s)

Mick is yet another graduate of the creative powerhouse that is the Young Chicago Authors (YCA) organization, a genuine “New School” linked to almost every up-and-coming Chi artist today. YCA has been an unbelievably positive influence in the lives of young artists all over Chicago and polished acts like the Huntsville, Alabama-born, Chicago-raised Mick Jenkins serve as evidence. Back in July, Mick officially signed with the Johnny Shipes-led Cinematic Music Group, a label known for giving their artists—like Big K.R.I.T, Joey Bada$$, and Smoke DZA—space to grow creatively. His latest mixtape, The Water(s), was met with near-universally positive press and featured a slew of other homegrown artists, such as Noname Gypsy and Jean Deaux (both happen to be on this list). With regards to the city that raised him, Mick told Complex “…the artists, themselves, of the drill movement of Chicago, they’re not the problem. As far as they go, I feel like they’ve got a story to tell. They have a voice and that shit’s real. The other side of what is going on in Chicago is like renaissance right now. It just needs to be shown. It just needs to be exposed to the public with the same amount of effort as the Drill side has.”

NoName Gypsy

Age: 23
Affiliation: N/A
Most Recent Mixtape or Album: N/A

One of the few non-Drill female emcees from Chicago, Noname Gypsy turned heads with her verse on Chance’s “Lost,” off of Acid Rap. Since then, she’s worked with Mick Jenkins, Saba, Taylor Bennett, and many other Chicago artists. Like Chance, Saba, and Mick, NoName is also an alumnus of Chicago’s YCA weekly “WordPlay” open mic for artistic-minded youths. This makes sense, as her verses are normally blessed with a heavy mix of spoken word and singing.  True to her name, NoName hasn’t put a lot of herself out in the public eye. Hopefully, it’s because she’s working on her solo debut, Telefone EP. Most recently, the young poet dropped “Dizzy” on her SoundCloud. We’ll see what comes next.

Leather Corduroys (Kami de Chukwu & Joey Purp)

Ages: 21 & 20, respectively
Affiliation: SaveMoney
Most Recent Mixtape or Album: Porno Music Volume II: TSFR

“We are who we are,” SaveMoney off-shoot, Leather Corduroys, tells HipHopDX. “We always are headed towards change. We never know until we get there.” Led by talented crew members Kami de Chukwu and Joey Purp, the Leather Corduroys are a duo to watch out for. Since dropping their debut track “The Prophet” featuring theMind last June, the young twenty-somethings have consistently done good work, showing strong improvement with each showing. A perfect example of this is the hilariously-named EP, Porno Music Vol. II. With no Vol. 1 ever released, Kami and Joey had fans confused, especially once Chance The Rapper dropped the EP through his personal Reddit account in April. Notable tracks since then include “Cheese Fondue With a Little Bit of Exercise” (yup) with Vic Mensa and OG Big Lurch and “Mexican Coke”, which dropped in September. They are said to be working on a full-length release. Joey Purp is also reportedly working on a performance art album to be named either Eyedrops or Performance Art

Jean Deaux (“john doe”)

Age: 19
Affiliation: The Village 777
Most Recent Mixtape or Album: N/A

Jean Deaux is still rocking braces, but that shouldn’t give the wrong impression of the 19-year-old’s maturity. “I’ve always had this mindset that you have to get it done, Deaux told Pure Dope Magazine. “Although Chicago is a place to live in, it’s never been easy for me at any point in my life. I’ve been homeless when I was little so, being my age and taking care of myself, I know that I have to get it done.” The kid who signed a publishing deal at 18 clearly has a mindset more world-ready than most actual adults and her toughness is on display in her music. Not to be defined as a rapper nor a crooner, Jean contributes an equal dose of both. Her RAW Series is comprised of four songs so far, including the light Sampha-produced “Find U” and tough-talking “T.M.S. Freestyle”, where Jean reveals that behind the sweet voice lives a confident soul. Most recently, you can listen to Jean Deaux’s “Healer”, off of Mick Jenkins’ The Water(s) project. She is said to be working on her debut album, Soular System.

Dinero Dynasty (Shazey & Runna Garcia)

Age(s): 22 and 24, respectively
Affiliation: N/A
Most Recent Mixtape or Album: Everything Local EP

Shazey and Runna Garcia hail from the West Side, like so many others on this list. Their debut EP is so enjoyable that it immediately warranted placement on this list. Given their sound, it’s not immediately apparent that they hail from the Windy City, a refreshing outside-the-lines audio coloring book with influences from all over the country, including a heavy Bay Area sound. They shared their feelings of optimism with HipHopDX: “It’s dope. The diversity is starting to show and it’s revealing that Drill isn’t the only sound from here. Everyone is doing great in their own way.” This positivity is no longer a lone rebellious thought lost in a sea of negative news. It’s becoming the norm. 

Honorable Mentions (Alphabetical Order):

Caleb James, Dally Auston, Defcee, God, Ibn Inglor, Jarred A.G., Kembe X, Logan, RondoNumberNine, SashaGoHard, Spenzo, Sulaiman, Tink, Towkio Shawn, Tree, ZMoney

Additional Reporting By: Patrick Guilfoyle & Josh Adams

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