These are Chicago’s 15 most influential rappers

Chicago’s Hip Hop scene has a rich and diverse history that mirrors the area’s complex cultural tapestry. Initially overshadowed by the East and West Coast’s early dominance, it soon carved out its own identity, distinguished by a blend of local street culture, dance, and production techniques. Now, some of rap’s most notable innovators – including Twista, Common, and Kanye West — proudly hail from the Windy City.

Chicago’s Hip Hop culture also gave rise to influential groups and movements. One collective, known as SAVEMONEY, featured artists like Chance the Rapper, Vic Mensa, and Towkio, and brought a new wave of independent, socially conscious rap to the forefront. Others like Do Or Die and Crucial Conflict carved niches that further added to the Midwest’s versatility.

More recently, Chi-Town’s drill music scene made a significant impact with rappers bringing the gritty, raw energy of the city’s streets to a global audience. Characterized by its dark beats and stark lyrical content, the now-international subgenre reflected the harsh realities of life in some of Chicago’s most challenging neighborhoods.

Below, REVOLT compiled a list of 15 artists who had a major part in Chicago Hip Hop’s evolution. All-in-all, the success and accolades of its biggest players are a testament to the city’s resilience, creativity, and cultural diversity.

1. Jitu The Jugganot

Jitu The Jugganot is a pioneering figure in music. He participated in the earliest rap events at the Blue Gargoyle community center and co-founded the New World Order, an organization representing Chicago’s rap artists. As a member of Ten Tray, he was also a part of the first Chi-Town rap group to secure a major label deal.

2. Kool Rock Steady

Originally from New York and a cousin of Afrika Bambaataa, Kool Rock Steady grew up in Chicago and became a major purveyor of hip house, a subgenre that mixed rap with electronic elements. His most notable tracks included “Turn Up the Bass,” “The Other Side Of Me,” and “You Ain’t Nobody,” a hard-hitting diss to hip house critic KRS-One. Tragically, he succumbed to HIV-related complications at the height of his career.

3. Lord Cashus D

Lord Cashus D is both an artist and educator who created New World Order alongside Jitu The Jugganot. He also established the first Chicago chapter of the Universal Zulu Nation under the guidance of Bambaataa. As an emcee, he performed with renowned artists like Public Enemy, Arrested Development, Queen Latifah, A Tribe Called Quest, The Last Poets, George Clinton, and KRS-One.

4. Crucial Conflict

Crucial Conflict, a quartet consisting of members Wildstyle, Kilo, Coldhard, and Never, found their niche within rap by blending stoner culture with an Old West-inspired sound. That mix culminated with the wildly successful hit “Hay” and the collective’s debut LP, The Final Tic. They would continue to hone their sound with subsequent drops like Good Side, Bad Side and individual efforts.

5. Do or Die

Do or Die gained initial success with “Po Pimp,” a collaboration with Twista and Johnny P that became a local hit and led to their signing with Houston’s Rap-A-Lot Records. The single’s wider release brought national exposure and paved the way for their classic debut LP, Picture This. Despite various obstacles, the trio of N.A.R.D., Belo Zero, and AK-47 remained active and consistent with a wealth of subsequent albums.

6. Twista

Twista is largely known for his lightning-fast, chopper-style delivery, which earned him recognition from Guinness World Records early in his career. With help from Kanye West, he ascended from the underground scene to the mainstream with his chart-topping single “Slow Jamz” and solidified his place in the popular realm with Kamikaze. Since then, the Chi-Town vet collaborated with a diverse range of artists, including Lil Jon, DJ Khaled, Mariah Carey, Lady Gaga, and more.

7. Common

Common (formerly Common Sense) is a highly influential artist known for sophisticated lyrics and political consciousness, consistently delivering top 10 releases despite evolving rap trends. The Chicago emcee made waves with songs like “I Used To Love H.E.R.,” an ode to the culture that led to a hotly contested battle with Ice Cube and Westside Connection. He would eventually find new levels of fame after aligning himself with West, which spawned albums like Be and Finding Forever.

8. Da Brat

Da Brat holds the distinction of being the first female rapper ever to score a platinum album via Funkdafied, which boasted singles like “Fa All Y’all,” “Give It 2 You,” and the LP’s title track. The first lady of Jermaine Dupri’s So So Def would continue to experience success with subsequent projects like Anuthatantrum and high-profile collaborations like “Not Tonight” alongside Lil’ Kim, Missy “Misdeameanor” Elliott, Angie Martinez, and Lisa “Left Eye” Lopes.

9. King Louie

King Louie, also known as King L, was a major factor in Chicago’s rap renaissance, especially regarding what eventually became known as drill. He’s just as resilient as he is prolific, having experienced a major car accident and being shot in the head. In addition to releasing a treasure trove of classic mixtapes, King L’s career highlights included working with West and aligning himself with Drake.

10. Kanye West

There may not be an artist, rapper or otherwise, from Chicago that made a bigger impact on music than West. Now known as simply Ye, the artist-producer transformed Hip Hop via his own barrier-breaking releases and contributions to countless others from his peers. His influence continues to reverberate throughout the culture. Ye’s constant reinventions were endless, from earlier days as a Roc-A-Fella signee to becoming a G.O.O.D. Music emperor.

11. Rhymefest

Rhymefest is largely known as a frequent collaborator of West’s. Together, the two co-wrote hit songs like “Glory,” “New Slaves,” and “Jesus Walks,” the last of which won a Grammy Award for Best Rap Song. Rhymefest experienced moderate success with his debut LP, the star-studded Blue Collar, and its follow-up, El Che. Outside of music, he also brought his cultural sensibilities to the political realm when he ran for Chicago’s 20th ward alderman and defended Hip Hop during a sit-down with former British Prime Minister David Cameron.

12. Shawnna

Before finding fame as a solo artist, Shawnna was one-half of Infamous Syndicate, a group that broke some serious ground with Changing the Game. The Chi-Town rapstress eventually signed with Ludacris’ Disturbing Tha Peace, where she delivered chart hits like “Shake Dat S**t” and the platinum-certified “Gettin’ Some.”

13. Lupe Fiasco

Lupe Fiasco is arguably one of the best lyricists of his generation. Known for his intricate wordplay, socially conscious themes, and diverse musical style, the Chicago wordsmith graduated from well-received mixtapes to his debut album, Food & Liquor, which earned him four Grammy nods. His subsequent albums, including The Cool and Lasers, further solidified his reputation as an influential figure in Hip Hop.

14. Chance The Rapper

Chance The Rapper’s unique blend of Hip Hop, gospel, and soul has garnered widespread recognition and critical acclaim. He gained prominence with his mixtapes 10 Day and Acid Rap, showcasing his distinctive style and introspective lyricism. He reached mainstream success with his Grammy Award-winning album Coloring Book, which made history as the first streaming-only LP to receive a Grammy nomination and win.

15. Chief Keef

Many consider Chief Keef to be the originator of drill music, a subgenre of rap that’s also taken over New York and London. Early in his career, Keef gained attention for his raw lyrics and distinctive flow, coupled with a production style molded by the likes of Young Chop and DJ Kenn. His breakout single, “I Don’t Like,” became a viral sensation and propelled him to national recognition, eventually catching the attention of West and spawning a high-profile remix. The rest is history.