Best Chicago drill rappers in 2022: Top dead and alive artists to ever do it

Best Chicago drill rappers in 2022: Top dead and alive artists to ever do it

The entertainment industry is evolving, and more artists are coming up with different music styles and genres. However, none has gained as much traction as drill rap. Drill's takeover of rap's biggest scenes over the last decade has been hard to beat, shaping a cultural movement stretching as far as Chicago, the U.K., and New York. Chicago drill rappers have defied all odds to release some of the most notable hits in 2022.

Best Chicago drill rappers
Photo: canva.com (modified by author)
Source: UGC

Chief Keef brought drill music to the masses and began to take off as a subgenre in 2021. All the while, it was attracting attention to the vibrant Chicago hip-hop scene. Later, Chicago drill rappers Lil Reese, Lil Durk and Lil Bibby were on everyone's radar, with the scene's trap productions and grim narratives giving something for people to latch on to.

Best drill rappers from Chicago

Drill shares some creative aspects with grime, borrowing many of the flows but using local slang and faster-paced beats than the genre's Midwestern origins. Check out the famous rappers from Chicago and catch up on some of their tracks to add to your playlists. The list contains the top alive and dead rappers.

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Top alive Chicago drill rappers

Below is a list of rappers that are still alive and still doing music:

1. Chief Keef

Why can't Durk perform in Chicago?
His music first became popular during his teen years in the early 2010s among high school students from Chicago's South Side. Photo: @Keith (modified by author)
Source: UGC

Who is the best drill rapper ever? Chief Keef is a legend from Chicago. He dropped his debut album, Finally Rich, in late 2012. In 2012, his popular local single I Don't Like was remixed by American rapper Kanye West and reached the Billboard Rap Top 20.

2. G Herbo

Who is the greatest Chicago rapper?
He is signed to Machine Entertainment Group. Photo by Quinn Harris
Source: Getty Images

G Herbo is a platinum-selling artist whose works have been reflected across America. He has released the mixtapes Welcome to Fazoland, Pistol P Project, Ballin Like I'm Kobe, and Strictly 4 My Fans. In 2021, he was a nominee in Forbes 30 under 30.

3. Chance The Rapper

Who was the first drill rapper from Chicago?
Johnathan Bennett, known professionally as Chance the Rapper, is an American rapper, singer-songwriter, and record producer. Photo by Noam Galai
Source: Getty Images

He released his debut mixtape, 10 Day, in 2012. After releasing his second mixtape, Acid Rap, he began to gain mainstream recognition in 2013. The celebrated rapper is already fired up with collaborations with different top artists.

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4. Polo G

Who is the best drill rapper ever?
Polo G released "Rapstar" in April 2021 as the third single from his third studio album, Hall of Fame. Photo by Timothy Hiatt
Source: Getty Images

Polo G's works in 2020 earned him spots in the billboard top performers. He rose to prominence with his singles Finer Things and Pop Out.

5. Calboy

Chicago hip hop artists
Calvin Lashon Woods, professionally known as Calboy, is an American rapper, singer, and songwriter. Photo by Bennett Raglin
Source: Getty Images

Calboy rose to fame after releasing the 2018 hot tune Envy Me. In 2017, Calvin had a breakthrough locally with his releases through Paper Gang Inc. Anxiety & Calboy the Wild Boy.

6. Liz Zay Osama

best Chicago drill rappers
The 25-year-old rapper was arrested after he allegedly left a machine gun in an Uber car. Photo: @Osama (modified by author)
Source: UGC

Liz Zay Osama is a 24-year-old and one the youngest Chicago hip-hop artists. He became famous following his single Changed Up, which garnered over 12 million views in under one month. Osama was arrested and charged with possessing a machine gun and being a felon in possession of a firearm.

7. Lil Durk

famous rappers from Chicago
He is the lead member and founder of the collective and record label Only the Family. Photo by Tim Mosenfelder
Source: Getty Images

Lil Durk is among the pioneers and one of the best drill rappers in Chicago. His release Laugh Now Cry Later, featuring Drake, gave him much-needed recognition in the music scene.

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8. Pinqy Ring

Marisol Vélez, better known by her stage name Pinqy Ring, uses the power of hip-hop to help others just as it helped her. Pinqy Ring is among the most influential American drill rappers. Some of her top songs include Trash It, Dear Diary, I Cry, etc.

9. Queen Key

Queen Key developed her love for singing and rapping at the young age of six. Queen Key has released multiple singles like Ratchet, among others.

10. Rico Recklezz

Chicago drill rappers killed
Rico has reportedly been incarcerated at Statesville Correctional Center since January 13 and has a scheduled release date in February 2024. Photo: @Bennett (modified by author)
Source: UGC

Rico Recklezz is a hip-hop recording artist from Chicago, IL. His popular diss tracks Hit Em Up and Call Recklezz garnered him thousands of fans worldwide. Rico collaborated with fellow Chicago rapper I.L Will for their collaborative mixtape Flatzz & Gunz 2.

Top Chicago drill rappers killed

Unfortunately, some top rappers met their death, but they left unending memories due to their melodic songs.

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1. Young Pappy

best drill rapper
His most popular songs include Faneto, Killa, and Savages. Photo: @Pappy (modified by author)
Source: UGC

He was a drill rapper from the North Side of Chicago, Illinois. Young Pappy was murdered at only 20 years old due to gang violence. He was one of the leaders of PBG (Poor Bear Gang), the notorious Gangster Disciples street gang.

2. Fredo Santana

dead chiraq rappers
Santana's addiction to prescription promethazine and codeine cough syrup may have contributed to his death. Photo by Johnny Nunez
Source: Getty Images

Fredo was the older cousin of Chicago rapper Chief Keef. Santana began recording music in 2011, releasing a series of mixtapes between 2012 and 2013. Santana died on January 19, 2018, due to complications from epileptic seizures.

3. Blood Money

Chicago rappers
After his death, Keef released a very emotional song about the loss of Blood Money. Photo: @Bloodmoney (modified by author)
Source: UGC

Blood Money was a member of the rap label Glory Boyz Entertainment (G.B.E.). He was Chief Keef's cousin. He was shot multiple times on April 9, 2014, and died in the hospital. Chief Keef was extremely close to Blood Money.

4. L'A Capone

Why can't Durk perform in Chicago?
L'A Capone was born Leonard Anderson on September 18, 1996, in the South Side of Chicago, Illinois. Photo: @Bloodmoney (modified by author)
Source: UGC

L'A Capone was an upcoming rapper closely associated with Lil Durk, who has appeared in some of his videos. L'A Capone was killed while leaving the studio after a late-night recording session on September 26, 2013. He is one of the dead Chiraq rappers.

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5. Lol Jojo

Who is the greatest Chicago rapper?
Coleman was only 18 when he was killed after trash-talking about rapper Chief Keef. Photo: @Joseph (modified by author)
Source: UGC

Born Joseph Coleman, Lol Jojo first became interested in rapping after hearing Lil Durk's L's Anthem on the car radio. He soon released B.D.K, a diss track aimed at the enemy crime gang Black Disciples. In September 2012, he was gunned down by an unknown assassin after mentioning his whereabouts on Twitter.

Who was the first drill rapper from Chicago?

Drill rap originated in southside Chicago around 2011. King Louie is considered one of the first drill rappers and the founder of Drill rap. Some pioneers of drill rap were Chief Keef, Lil Reese, Lil Durk, Rondonumba9, LA Capone (R.I.P), and more.

Who is the greatest Chicago rapper?

Kanye West is regarded as the greatest Chicago rapper. He is one of the most critically acclaimed artists of the 21st century and is regarded as one of the most influential hip-hop artists of all time.

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Why can't Durk perform in Chicago?

Rapper Lil Durk suffered an injury during his Lollapalooza 2022 performance. While performing a set at the Chicago music festival on Saturday, the 29-year-old Broadway Girls rapper was injured after onstage pyrotechnics went off right in front of him.

What is Chicago rap called?

The drill is a subgenre of hip-hop music that originated in Chicago streets in the early 2010s.

Who is the first rapper from Chicago?

Kurtis Blow became the first rap artist to sign a record deal with a major label, and his anthem, The Breaks, would take the country by storm in 1980.

Who is the richest female rapper?

Minaj has worked with some of the best rappers in the world, and she is the wealthiest female rapper right now. As of October 2022, Nicki Minaj's net worth is roughly $100 million, making her the richest female rapper in the world.

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Rap is continually revolutionizing the hip-hop scene. The biggest beneficiary of this revolution is Chicago city. The rappers are continuously taking top spots in the charts. Unfortunately, many young and talented Chicago drill rappers are still killed due to senseless gun and gang-related violence.

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Source: Briefly News

Authors:
Bennett Yates avatar

Bennett Yates (Lifestyle writer) Bennett Yates is a content creator with over five years of working experience in journalism and copywriting. He graduated from the University of Nairobi (2017) with a Bachelor's in Information Technology. In 2023, Bennett finished the AFP course on Digital Investigation Techniques. He started working for Briefly in 2019. You can reach him via email at bennetyates@gmail.com.