The Best Chicago Rappers

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"The Best Chicago Rappers" list features a selection of talented hip-hop artists who have left an indelible mark on the music scene.

From the gritty streets of Chicago, these rappers have risen to prominence with their unique styles, powerful lyrics, and innovative contributions to the genre. With diverse influences and stories to tell, each artist on this list has captivated audiences worldwide and solidified their place in hip-hop history as some of the finest representatives of Chicago's rich musical legacy.


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  1. Kanye West

    Kanye West is a Grammy Award-winning rapper, producer and fashion designer. His outspoken nature has made him a polarizing figure in popular culture.

    Kanye West is a singer, rapper and producer. He has released 8 studio albums and 22 singles. He is also a fashion designer, having collaborated with Nike to design shoes for their Air Yeezy line. Kanye West is a very influential person in the hip-hop industry. He was ranked by Billboard as one of the most successful artists of all time in 2017. He has won more than 20 Grammy Awards and 2 Emmy Awards from his work as a musician, producer, fashion designer and entrepreneur.
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  2. Juice WRLD

    Juice WRLD, whose real name was Jarad Higgins, was an American rapper, singer, and songwriter.

    He gained significant popularity for his melodic style and emotionally raw lyrics, often focusing on themes of heartbreak, mental health, and substance abuse. Born on December 2, 1998, in Chicago, Illinois, Juice WRLD rose to prominence with his breakout single "Lucid Dreams," which peaked at number two on the Billboard Hot 100 chart.

    Throughout his career, Juice WRLD released several successful projects, including his debut studio album "Goodbye & Good Riddance" (2018) and his second album "Death Race for Love" (2019). He was known for his prolific output, frequently releasing music and collaborating with other artists. Despite his young age and promising career, Juice WRLD tragically passed away on December 8, 2019, at the age of 21, due to an accidental drug overdose. His death deeply saddened fans and fellow musicians, and his legacy continues to influence the music industry.

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  3. Polo G

    Polo G, born Taurus Bartlett on January 6, 1999, is an American rapper and songwriter from Chicago, Illinois. He gained widespread recognition with his debut single "Finer Things" in 2018, which garnered millions of views on YouTube and helped him build a significant following.

    Polo G, born Taurus Bartlett on January 6, 1999, is an American rapper and songwriter from Chicago, Illinois. He gained widespread recognition with his debut single "Finer Things" in 2018, which garnered millions of views on YouTube and helped him build a significant following.

    In 2019, Polo G released his debut studio album, "Die a Legend", which received critical acclaim and solidified his position as one of the rising stars in hip-hop. The album featured tracks like "Pop Out" featuring Lil Tjay, which became a commercial success and further boosted his popularity.

    Polo G continued his success with subsequent projects, including his sophomore album "The Goat" (2020), which debuted at number two on the Billboard 200 chart. The album showcased Polo G's introspective lyrics and versatile flow, earning praise from both fans and critics.

    Known for his poignant storytelling and gritty delivery, Polo G often addresses themes such as street life, resilience, and personal struggles in his music. His authenticity and lyrical prowess have solidified his status as one of the most promising young talents in the rap scene.

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  4. King Von

    King Von was an American rapper known for his gritty storytelling and portrayal of street life.

    Rising to fame with his breakout single "Crazy Story" in 2018, he solidified his status as a rising star in hip-hop with subsequent releases and collaborations. His debut album, "Grandson, Vol. 1", further showcased his raw lyricism and storytelling abilities. Tragically, King Von's life was cut short when he was fatally shot outside a nightclub in Atlanta on November 6, 2020. Despite his untimely passing, his music continues to resonate with fans, and he remains a respected figure in the rap scene.

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  5. Chief Keef

    Chief Keef, whose real name is Keith Farrelle Cozart, is an American rapper, singer, and record producer from Chicago, Illinois.

    Born on August 15, 1995, Chief Keef gained significant attention in the early 2010s for his distinctive drill music style, characterized by its aggressive beats and lyrics reflecting the realities of inner-city life.

    Keef gained widespread recognition with his viral hits, including "I Don't Like" and "Love Sosa", which helped propel him to mainstream success. His debut studio album, "Finally Rich", was released in 2012 and featured these popular tracks. His unique sound and rise to prominence influenced a new wave of hip-hop artists and solidified his status as a key figure in the Chicago rap scene.

    Despite his early success, Chief Keef's career has been marked by legal troubles and controversies. He faced various legal issues, including firearms charges and probation violations, which affected his ability to travel and perform. Despite these challenges, Chief Keef has continued to release music independently and remains a respected figure in hip-hop, known for his influential contributions to the genre.

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  6. Lil Durk

    Lil Durk, born Durk Derrick Banks, is an American rapper, singer, and songwriter from Chicago, Illinois.

    Rising to prominence in the early 2010s, he became known for his contributions to the drill music scene alongside artists like Chief Keef and King Von. Durk signed with Def Jam Recordings in 2012 and released his debut studio album, "Remember My Name", in 2015. Known for his introspective lyrics and melodic flow, Durk has continued to release successful mixtapes and albums, including "Signed to the Streets 3" (2018) and "Just Cause Y'all Waited 2" (2020). He has collaborated with numerous artists across genres and remains a respected figure in contemporary hip-hop, addressing themes such as street life, violence, and perseverance in his music.

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  7. G Herbo

    G Herbo, born Herbert Wright III, is an American rapper and songwriter from Chicago, Illinois.

    Rising to prominence in the drill music scene, he gained recognition for his raw lyricism and candid portrayal of street life. Herbo's debut mixtape, "Welcome to Fazoland", released in 2014, showcased his storytelling abilities and earned critical acclaim. He followed up with successful mixtapes like "Ballin Like I'm Kobe" before releasing his debut studio album, "Humble Beast", in 2017. Throughout his career, Herbo has addressed social issues such as violence and poverty in his music, offering insight into life in inner-city Chicago. He remains respected for his authenticity and dedication to his craft, while also being involved in community initiatives to support disadvantaged youth and address social issues.

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  8. Chance the Rapper, born Chancelor Johnathan Bennett, is an American rapper, singer, songwriter, and philanthropist from Chicago, Illinois.

     He gained prominence with mixtapes like "10 Day" and "Acid Rap", showcasing his innovative lyricism and vibrant production. His third mixtape, "Coloring Book", won a Grammy Award for Best Rap Album, making history as the first streaming-only project to do so. Beyond music, Chance is known for his philanthropic efforts in Chicago, particularly in education and social justice. He continues to be a prominent figure in hip-hop, known for his positive vibes, Christian faith, and commitment to making a difference in his community.

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  9. Lil Reese

    Lil Reese, born Tavares Lamont Taylor, is an American rapper from Chicago, Illinois, known for his contributions to the drill music scene

    He gained prominence through collaborations with Chief Keef and solo mixtapes like "Don't Like" and "Supa Savage". Despite facing legal issues and controversies, Lil Reese has continued to release music independently, known for his gritty delivery and street-oriented lyrics. He remains a recognizable figure in hip-hop, known for his raw authenticity and contributions to Chicago's rap scene.


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  10. Fredo Santana, born Derrick Coleman, was an American rapper and record producer known for his contributions to the drill music scene in Chicago, Illinois.

    He gained recognition through mixtapes like "It's a Scary Site" and "Fredo Kruger" and was a prominent figure in the genre alongside his cousin Chief Keef. Fredo founded Savage Squad Records and released several projects under it. Tragically, he passed away on January 19, 2018, at the age of 27, due to complications from substance abuse. Despite his untimely death, Fredo Santana's legacy endures through his music, which continues to influence the hip-hop community.

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  11. Lil Bibby

    Lil Bibby, born Brandon George Dickinson Jr., is an American rapper and songwriter from Chicago, Illinois.

    He gained recognition in the hip-hop scene with his debut mixtape "Free Crack" in 2013, showcasing his raw lyricism and gritty portrayal of life in Chicago's streets. Bibby continued to release successful mixtapes, collaborating with artists like Lil Herb (G Herbo) and establishing himself as a rising star in the genre. In addition to his music career, Bibby has been involved in entrepreneurship and philanthropy, aiming to uplift underserved communities in Chicago. While he has taken a step back from releasing music recently, his impact on hip-hop, particularly in Chicago, remains significant, with his authentic storytelling and contributions to the genre remembered by fans and fellow artists alike.

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  12. Famous Dex

    Famous Dex, born Dexter Gore Jr., is an American rapper, singer, and songwriter from Chicago, Illinois.

    He gained recognition for his energetic delivery and catchy ad-libs, rising to prominence with mixtapes like "Never Seen It Coming" and "Dexter's Laboratory." Dex further solidified his status as a rising star with the hit single "Pick It Up" featuring ASAP Rocky. Despite personal struggles with substance abuse, he remains open about his experiences and uses his platform to raise awareness about mental health. Dex has also explored acting and fashion alongside his music career, continuing to release music and collaborate with other artists while maintaining a prominent presence in the hip-hop community.


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  13. Montana of 300, born Walter Anthony Bradford, is an American rapper known for his lyrical prowess and rapid-fire delivery.

     Hailing from Chicago, Illinois, he gained recognition with his debut mixtape "Cursed with a Blessing" in 2014. Montana's thought-provoking lyrics and aggressive style have earned him a dedicated fanbase and respect in the hip-hop community. He addresses topics such as street life and social issues in his music, showcasing his versatility as an artist. Despite being an independent artist, Montana continues to release music and perform live, maintaining his prominence in the rap scene.

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  14. Lupe Fiasco, born Wasalu Muhammad Jaco, is an American rapper, record producer, and entrepreneur from Chicago, Illinois.

    Known for his intricate lyricism and socially conscious themes, he gained recognition with his debut album "Lupe Fiasco's Food & Liquor" in 2006, followed by "Lupe Fiasco's The Cool" in 2007. Throughout his career, Lupe has released several more albums, blending elements of hip-hop, jazz, and other genres. He is also involved in entrepreneurial ventures and philanthropic efforts. Lupe remains a respected figure in hip-hop, admired for his intellect, creativity, and dedication to addressing social issues through his music.

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  15. Twista

    Twista, born Carl Terrell Mitchell, is an American rapper known for his rapid-fire delivery and tongue-twisting rhymes.

     Hailing from Chicago, Illinois, he gained fame in the late 1990s and early 2000s with albums like "Adrenaline Rush" and "Kamikaze", featuring hits such as "Slow Jamz". Twista's versatile flow and ability to collaborate across genres have solidified his influence in the hip-hop community. He continues to release music and perform live, maintaining his status as one of the genre's respected figures. Twista's technical skill and contributions to rap have earned him acclaim beyond his chart success.

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  16. Vic Mensa

    Vic Mensa, born Victor Kwesi Mensah, is an American rapper, singer, songwriter, and activist from Chicago, Illinois.

    He gained recognition as a member of the hip-hop collective SaveMoney before launching a successful solo career. Mensa's music often addresses personal struggles and social issues such as police brutality and racism. He gained critical acclaim for his mixtape "Innanetape" and his debut studio album "The Autobiography". Mensa is also known for his activism and advocacy work, particularly around racial justice and mental health awareness. He continues to use his platform to shed light on important issues while captivating audiences with his diverse musical style and introspective lyricism.

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  17. Earl Sweatshirt, born Thebe Neruda Kgositsile, is an American rapper, songwriter, and record producer hailing from Chicago, Illinois.

    He gained prominence as a member of the hip-hop collective Odd Future. Earl garnered attention with his debut mixtape "Earl" in 2010, showcasing his intricate wordplay and introspective lyricism. His albums "Doris" (2013) and "I Don't Like Shit, I Don't Go Outside" (2015) further solidified his reputation for exploring themes of mental health and personal growth. Despite maintaining a low profile, Earl Sweatshirt continues to release music independently, earning acclaim for his unique style and uncompromising artistic vision.

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  18. King Louie

    King Louie, born Louis King Johnson Jr., is an American rapper from Chicago, Illinois, known for his contributions to the drill music genre.

    Rising to prominence with mixtapes like "Boss Sh*t" and tracks like "Val Venis", he has become a respected figure in the Chicago rap scene. Despite facing personal and professional challenges, including surviving a shooting incident in 2015, King Louie continues to release music independently and collaborate with other artists. His raw lyricism and energetic delivery have solidified his place as a prominent figure in Chicago hip-hop.


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  19. Noname

    Noname, born Fatimah Nyeema Warner, is an American rapper, poet, and record producer from Chicago, Illinois.

    She gained recognition with her mixtape "Telefone" in 2016, known for its introspective lyricism and soulful production. Noname is admired for her unique blend of hip-hop, jazz, and spoken word poetry. Beyond music, she is involved in activism, particularly around issues of racial justice. Noname continues to release music independently and is celebrated for her innovative approach to hip-hop.

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  20. Soulja Boy

    Soulja Boy, born DeAndre Cortez Way, is an American rapper, producer, and entrepreneur hailing from Chicago, Illinois.

    He gained widespread fame with his viral hit single "Crank That (Soulja Boy)" in 2007, which sparked a dance craze and propelled him to stardom. Soulja Boy continued to release music and establish himself as a prominent figure in hip-hop, also venturing into entrepreneurship with his own record label and fashion line. Despite facing legal issues and controversies, he remains influential in the industry, known for his impact on internet culture and the rap genre.

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