Top 25 Chicago Rappers of All Time

Chicago’s music scene has birthed iconic rap stars who’ve shaped hip hop nationwide. This definitive ranking will count down Chi-Town’s finest MCs starting at #25 down to Chance the Rapper at the #1 spot.

These rappers were selected based on criteria like lyricism, discography, classics, longevity, influence, commercial success, and cultural footprint within rap. From gangsta rap pioneers to new school drill trailblazers, let’s explore the 25 best Chicago rappers ever.

#25. G Herbo

Formerly known as Lil Herb, rapper G Herbo emerged onto Chicago’s drill scene as a teenager in the early 2010s. His gritty mixtapes like 2012’s Welcome to Fazoland and 2014’s Pistol P Project showcased vivid storytelling about gang life over hard-hitting beats. Tracks like “Kill Shit” with Lil Bibby built his buzz. G Herbo’s solid output and collabs earned him XXL Freshman honors in 2016 as he crossed over more into mainstream success.

#24. Vic Mensa

After rising in Chicago’s alternative hip hop circuit with collective SAVEMONEY, Vic Mensa landed on major radars through his 2015 single “Down on My Luck.” His debut The Autobiography and collaborations with Kanye West and Ty Dolla $ign followed. Known for his socially conscious lyrics, Vic Mensa represents a progressive voice among Chicago’s recent wave blending hip hop with EDM and rock influences.

#23. Lupe Fiasco

Born Wesley Lupe Fiasco, this rapper first hit the scene in 2006 with critically acclaimed Food & Liquor, earning him three Grammy nods. His sharp lyrics built buzz alongside productions from legends like Kanye West, Pharrell and Soundtrakk. Singles “Kick, Push” and “Superstar” displayed a penchant for storytelling. Though some later albums proved polarizing, Lupe Fiasco’s early work cemented him as one of Chicago’s most skilled lyricists.

#22. Juice WRLD

Emerging from the online SoundCloud rap movement, Juice WRLD found breakout success with hits like 2018’s “Lucid Dreams.” His major label debut Goodbye & Good Riddance contained more emotional trap-rap cuts. Juice WRLD’s melodic style and introspective lyrics on tracks like “Legends” connected widely before his untimely 2019 passing at just 21 years old. He left a considerable influence on post-2000s Chicago rap.

#21. Twista

Setting Guinness World Records for fastest rapping, Twista skyrocketed in the early 2000s through his blistering triple-time flows. 2004’s Kamikaze went to #1 behind the Kanye and Jamie Foxx collab “Slow Jamz.” Twista dominated midwest radio alongside fellow Chicagoans like Do or Die. Though less prolific recently, rapid-fire tracks like “Adrenaline Rush” cemented his notoriety.

#20. Da Brat

As one of rap’s pioneering female MCs, Da Brat repped for Chicago starting with her 1994 debut Funkdafied that introduced her slick style. Hits like “Funkdafied” and “Po Pimp” spawned platinum plaques. Later work with Mariah Carey and label boss Jermaine Dupri kept her visible. Brat also acted in films and TV. Her confident attitude and flow inspired future female rappers to be bold.

#19. Shawnna

Female rapper Shawnna first garnered attention through Ludacris’ Disturbing Tha Peace label in the early 2000s. She appeared on hits like “Stand Up” before dropping her fierce solo debut Worth tha Weight in 2004 led by single “Shake Dat Shit” featuring Luda. Shawnna’s raunchy lyrics and nimble flow on tracks like “Damn” earned her the moniker Queen of Tha Ghetto. Though brief, her thrilling output left an impact.

#18. King Louie

Known as one of Chicago’s early drill scene architects, King Louie often cites Kanye West as the fuel for his swaggering mixtape grind starting in the late 2000s. Tracks like “Val Venus” spread his soulful delivery ahead of 2013’s March Madness banger “Bitch I’m Posh.” While his studio debut suffered setbacks, King Louie’s influence helping drill go viral as Chicago’s next hip hop wave after trap cannot get understated.

#17. CupcakKe

The raunchy bars and hypersexual imagery from female rapper CupcakKe draws obvious comparisons to Lil Kim. But with tracks like “Deepthroat,” she also showcases intricate flows and a tongue-twisting rhyming ability. After early mixtapes, CupcakKe earned more mainstream looks in 2018 with Ephorize earning a Billboard top 40 spot. Never one to hold back, CupcakKe displays creativity through confrontational lyricism.

#16. Common

As one of Chicago’s most respected rap veterans, Common (formerly Common Sense) broke through in the 90s with tracks like “I Used to Love H.E.R.” and “The Light.” His 1994 album Resurrection remains vital. Though branching into acting limited his music, conscious classics like “Retrospect for Life” retain influence. Common’s passion for uplifting the city and black community remains constant.

#15. Chief Keef

The monotone ad-lib master Chief Keef symbolizes Chicago drill’s early 2010s commercial breakthrough. Sharing raw stories about drug dealing and violence in Englewood, tracks like “Love Sosa” and “I Don’t Like” made Keef rap’s newest antihero. Legal controversies couldn’t stop his debut Finally Rich impacting. Chief Keef’s Itunes start-up Glo Gang also founded fellow hitmakers like Lil Reese. His influence looms large.

#14. Lil Durk

Originally aligned with Chief Keef’s Glory Boys crew, rapper Lil Durk carved his own lane repping Chicago drill with vulnerable street tales and an R&B-flavored style. Mixtapes like Signed to the Streets and Remember My Name built momentum before Lil Durk crossed over into melodic trap rap on albums like 2020’s Just Cause Y’all Waited 2 and collabs with Drake. His longevity and stylistic shakeups keep him relevant.

#13. Do or Die

This pioneering trio helped put Chicago’s rap scene on the map in the 1990s through hard-hitting albums like Picture This, Back 2 The Game and Headz or Tailz. Their 1996 hit “Po Pimp” ushered in the city’s gruff street rap style. Twista’s rapid-fire flow paired dynamically with Belo Zero and N.A.R.D.’s perspectives. Do or Die set the foundation for common Midwestern rap touchstones like cars, hustling and clashing gangs.

#12. Crucial Conflict

Known for 1996 smash “Hay” produced by rising star No I.D., Crucial Conflict epitomized Chicago’s rowdy 90s booty bass movement fusing rap with dance music samples. Wild Weekend also featured aggressive tracks like “Desperados” and “Scummy” putting Cold World Entertainment’s rapid-fire lyricism on display. The foursome’s pulverizing sound reflected party rap’s harder edge at the time.

#11. Twista

As mentioned earlier, Guinness World Record holder Twista remains one of rap’s fastest spitters ever since dominating radio in the early 90s. His trademark chopper style featured feverish triple-time rapping over drum-heavy beats. 2004’s Kamikaze launched Twista into more mainstream success thanks to the Kanye collab “Slow Jamz” reaching #1. Twista’s early albums helped certify Chicago as a respected hip hop hub.

#10. Yung Berg

Before landing pop hits in the 2010s, Chicago native Yung Berg emerged in 2007 with rap club banger “Sexy Lady” highlighting his talent for slick rhymes and catchy hooks. The single became an urban anthem and launched his album Look What You Made Me. Berg later appeared on reality shows to stay visible. While his success faded, Berg’s ability to mesh rap with R&B hitmaking planted seeds for future artists like Juice WRLD.

#9. Bump J

Veteran MC Bump J gained traction in the 2000s through his collaborations with hometown legends like Twista and producer NO I.D. His 2005 track “Move Around” featured on the compilation The Champions became a local smash and led to his own mixtape circuit domination. Though incarceration stalled his career, Bump J’s prolific independent grind and uptempo flow inspired Chicago’s next generation.

#8. Common

One of Chi-Town’s most respected lyricists, Common rose up in the 90s underground scene before achieving massive critical acclaim. Albums like Resurrection and Be contained conscious lyricism and vintage production. When not acting, Common stays dedicated to uplifting his community and black culture overall through spiritual music. With 10 albums and a Grammy, the rapper/actor’s positivity remains integral to Chicago hip hop’s identity.

#7. King Louie

The influential King Louie earned the unofficial crown as “King of Drill” in Chicago for early mixtape domination in the late 2000s/early 2010s. His hypnotic rhymes over stark, hazy beats defined the subgenre’s vibes. Tracks like “Val Venis” and “Bitch I’m Posh” forged his signature style. Though major label success eluded him, Louie still deserves credit for helping put Chicago’s gritty drill scene on the map.

#6. G Herbo

Currently signed to Machine Gun Kelly’s label, G Herbo emerged as one of drill’s mostimportant MCs with his Welcome to Fazoland mixtape in 2014. His gruff delivery and real street tales delivered at rapid-fire pace cemented him alongside Chief Keef and Lil Durk. Tracks like “Kill Shit” with Lil Bibby united Chicago’s young talent. Herbo’s continued success keeps him among the city’s elite faces.

#5. Lupe Fiasco

Hailing from Chicago’s West Side, Lupe Fiasco transcended styles as a wordsmith with versatile lyrical abilities and flows. His 2006 album Food & Liquor earned him three Grammy nods and acclaim for hits like “Kick, Push” and “Daydreamin’.” Never one to chase trends, Lupe carved his own artistic lane. His exceptional early work should be revisited by any fan of lyrical hip hop.

#4. Juice WRLD

The meteoric rapper Juice WRLD left fans heartbroken when he tragically passed in 2019 at just 21 years old. Coming up on SoundCloud, he broke through with emo-rap smash “Lucid Dreams” and his 2018 major label debut Goodbye & Good Riddance. Juice defined a generation with vulnerable lyrics about anxiety, drugs, and heartbreak. His outsider anthems connected with millions, leaving a huge imprint for such a short career.

#3. Kanye West

Before becoming one of music’s most famous figures, Kanye first produced for hometown talent like Jermaine Dupri and Jay-Z in the 90s before going solo in the 2000s. His early albums The College Dropout, Late Registration and Graduation made him a star with unique production blending soul and electronic music. By pursuing artistic growth rather than gangsta rap trends, the mercurial Kanye redefined hip hop fame ideals.

#2. Da Brat

The acclaimed female MC Da Brat became one of the first commercially successful women in rap, repping for Chicago starting with 1994’s platinum-selling Funkdafied. Her rapidfire flow and swagger on hits like “Funkdafied” and “Po Pimp” paved the way for future female MCs to be fiery and outspoken. Along with acting, Da Brat collaborated with Mariah Carey and others while mentoring young talent like Shawnna. Her legacy as a hip hop trailblazer persists.

#1. Chance the Rapper

The underground mixtape dynamo Chance The Rapper became an unconventional hip hop superstar in the 2010s through his soulful, jazzy sound receiving critical acclaim. 2013’s Acid Rap brought internet fame that turned mainstream through hit collaborations and albums like 2016’s Grammy-winning Coloring Book. Chance’s musicality stands out among drill scene shoutability. By independently staying true to his style, he became Chicago’s current greatest hip hop ambassador.

The History of Chicago Hip Hop

Chicago’s hip hop history began in the early 1980s with radio DJs like Jesse Saunders and Kenny “Jammin” Jason spinning breakbeats. Original b-boy crews like the Fantastic Four gained renown. Early rap duo Renaldo Domino released the first Chicago hip hop single in 1984 “Rain or Shine.”

The 1990s saw Do or Die, Crucial Conflict and Da Brat bring Chicago onboard rap’s national wave. Producer No I.D. mentored Kanye West and Common locally. Underground acts like All Natural and Rubberoom formed a grassroots scene. Raw booty house dance music fused with rap as the aggressive ghettotech sound.

Kanye West, Common, Twista, Rhymefest and Lupe Fiasco represented Chicago’s diverse talent in the 2000s. The gritty drill subgenre led by Chief Keef emerged in the early 2010s followed by the bop dance rap movement out of the South Side. Recent stars like Chance the Rapper, Noname, Saba, Valee, Calboy and Polo G now lead the new school.

The Impact of Chicago Hip Hop Culture

From Kanye to Chance, Chicago rappers expanded sonic limits by avoiding gangsta cliches. Twista and Da Brat paved paths for speedy or fiery female rappers. Do or Die, Crucial Conflict and Psychodrama produced party anthems that also meant something deeper. Drill exposed the voiceless South Side’s struggles.

Though some rap beefs turned violent, Chicago’s DIY mixtape hustle and artist incubators like Closed Sessions offer opportunities. Kanye proved rappers could produce their own beats. Overall, Chi-Town MCs keep it real while progressing hip hop forward. The city’s blue-collar ethos and musical diversity inspired innovation.

Frequently Asked Questions

Who are considered pioneers of Chicago hip hop?

Early DJs like Kenny “Jammin” Jason and Jesse Saunders helped originate Chicago hip hop by spinning breaks. Rapper Renaldo Domino had the first local hip hop single in 1984 “Rain or Shine.” Graffiti artist Ray Mock was influential in the scene too.

What record labels have been important in Chicago?

Important indie labels have included Common’s Relativity Records imprint, Touch & Go Records launching local acts, Underground Soljahs from Rhymefest, Lupe Fiasco’s 1st & 15th, and Chief Keef’s Glo Gang/Glory Boyz Entertainment label collective.

How did drill music originate?

Drill originated on the violent, impoverished South Side as young rappers like Chief Keef and Lil Durk used it as an outlet, making ominous songs over hard-hitting beats about the threats they faced. The urgent music went viral fast in the early 2010s.

How has Chicago rap influenced American hip hop?

Kanye West’s innovative artistic approach inspired risk-taking in hip hop. Twista and Da Brat pioneered rapid-fire flows. Common’s consciousness influenced many. Chief Keef took drill global. Chance the Rapper’s indie success broke molds. Many styles started in Chicago.

Who are the most commercially successful Chicago rappers?

Kanye West, Chance the Rapper, Lupe Fiasco, Common, Twista, Chief Keef and Juice WRLD have attained the highest levels of mainstream success through album sales, radio play, and features.