Here’s our list of our favorite Chicago Drill Rappers and hip hop artists.
Our list includes: Lil Durk, L’A Capone, Fredo Santana, Chief Keef, FBG Duck, Young Pappy, Wooski, Lil Jay, Dooski, G Herbo, S.dot, King Samson, P.Rico, Famous Dex, 600 Breezy, D.Rose, Montana of 300, Edai, RondoNumbaNine, Cdai, Billionaire Black, King Louie, and many more.
Drill Rappers from Chicago
In 2012, Drill music exploded into the mainstream music world when Kanye West released a remix of Chief Sosa’s hit, “I Don’t Like.”
Chicago Rappers That are Still Alive
Additionally, here’s a list of rappers and entertainers from Chicago that are still active and making music.
Unfortunately, many talented rappers are affiliated with Chicago Gangs, only leading to a life of violence or prison.
Please keep in mind:
Sadly, this list may change due to the extreme violence in Chicago. Some Rappers may be added or subtracted from the list due to overdose, gang violence or incarceration.
- Lil Durk
- Rico Recklezz
- G Herbo
- Chief Keef
- King Louie
- Ewol Samo
- Prince Eazy
- P.Rico
- Montana of 300
- Killa Kellz
- Edai
- Prince Dre
- Famous Dex
- Lil Bibby
- Ewol Samo
- Lil Jay
- FBG Duck
- Billionaire Black
- S.Dot
- D.Rose
- 600 Breezy
- King Samson
- Wooski
- Cdai – (Convicted of 1st-degree murder).
- RondoNumbaNine – (Convicted of 1st-degree murder).
Chicago Drill Rappers That’ve Died
Unfortunately, many young and talented rappers from Chicago lose their lives due to senseless gun and gang-related violence.
Some of the hip hop artists and rappers who’ve died from gun violence in Chicago include; OTF Nunu, L’A Capone, Lil Jeff, CantGetRight, Lil Marc, Lil Mister, Lil Jojo, Young Pappy, Blood Money, Brick, and many more.
Rappers that have passed away include:
- L’A Capone
- Fredo Santana
- Lil Jojo
- (Montana) Lil Mister
- Lil Marc
- Capo
- Blood Money
- Dooski
- Young Pappy
- OTF Nunu
- Lil Jeff
- Can’tGetRight
- Smylez
L’A Capone
Capone was a special artist and record labels started noticing. The amount of talent that L’A had was incredible, and his life was taken so young.
L’A Capone, was shot to death while leaving the studio after a late-night recording session on September 26, 2013.
Fredo Santana
Santana was pronounced dead on January 19, 2018 due to complications from epileptic seizures. Santana’s addiction to prescription promethazine and codeine cough syrup may have contributed to his death.
Coleman was one of the last real old-school artists. Fredo was misunderstood by the media, but his marketing savvy allowed him to work with artists like Drake and Kendrick Lamar.
Lil Jojo
Joseph Coleman, better known as ‘Lil Jojo’, was shot to death during a drive-by shooting on September 4th, 2012.
Lil Mister
Lil Mister (Montana) —real name Antwon Fields—sustained a bullet wound to the head on March 16, 2019 at around 7:15 p.m. local time in the Englewood neighborhood.
In a 2017 interview with ZackTV, Mister spoke about the death of his extremely close friend Lil Jojo, as well as the advice Durk gave him about dealing with beef.
Unfortunately, Antwon was taken to the University of Chicago Medical Center, where he was later pronounced dead.
Facts about Lil Mister
- Lil Durk and Mister are actually cousins.
- Best Song – No Lackin.
Blood Money
Mario Hess, who also went by the stage names Blood Money and Big Glo – was shot in the chest outside his family’s home in the 5600 block of South Elizabeth Street around 9:30 p.m on April 9, 2014.
Chief Keef was extremely close to Blood Money, and after his death, Keef released a very emotional song about the loss of Blood Money.
Chief Keef’s Song Dedicated to Blood Money
Also, Keef released the song Ain’t Missing You feat Jenn Em, as a Tribute To Big Glo.
Dooski
Although Dooski wasn’t a well-known rapper, he was definitely well respected in the streets and among the Gangster Disciples.
Dooski Tha Man was a well-known and beloved member of MOB/ScrappGang and artist. Dooski has a song with Wooski called “Shooters.”
Mass Shooting at Dooski’s Funeral
Detectives are looking into a possible connection to a mass shooting in the afternoon outside the Bethlehem Star Missionary Baptist Church at 9231 S. Cottage Grove Ave.
Furthermore, The funeral was for rapper Vantrease “Dooski Tha Man” Criss, killed earlier this month in a drive-by shooting about a mile from the shooting. The shootout occurred on a main business drag in the Burnside neighborhood.
Consequently, Dooski Tha Man was killed Oct 9 on his block with a shot to the head, he was only 25 years old.
Lil Marc
View D.rose’s deleted video from the Lil Marc hit.
Capo
Young Pappy
Lil Jeff
Smylez
Our List Of The Best Rappers from Chicago
Check out our list of the best rappers from Chicago, IL. Our list includes not only drill rappers, but simply the most influential rappers from the Chi.
Furthermore, even though Kanye west was an easy choice, how could you not include Chance the rapper and Twista among the top 5?
- Kanye West.
- Chance the Rapper.
- Twista.
- Common.
- Lupe Fiasco.
- Lil Durk.
- Chief Keef.
- Lil Jay.
- Lil Jojo.
- G Herbo.
“Crank That” — Rico Recklezz Soulja Boy (Diss)
Watch the “Crank That” Soulja Boy Diss track video by Rico Recklezz.
[Rico Recklezz disses Chicago Artists] Hit Em Up – Rico Recklezz
Rico Recklezz encourages other rappers from Chicago to step up and start releasing more music. It was aimed as a friendly diss track, but some various other artists obviously took offense. Famous Dex decided to laugh it off, while others fired back.
Rico Recklezz Interview: Why Drill Music Will Never Die out
Rico Recklezz sits down with DJ Small Eyes and discusses…