Drill Rappers

Drill Rappers
Drill Rappers – A list of drill rappers from Chicago with an updated list of living or deceased artists as of 2023.

It’s important to note that these artists’ legacies live on through their music and the impact they made on the hip-hop community, both in Chicago and beyond.

Drill Rappers.

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.

Chicago Drill Music

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.

Drill Rappers from Chicago
Drill Rappers from Chicago

Chicago Drill Rappers Alive in 2023

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.

G Herbo Active in 2019.
G Herbo in 2019.

Please keep in mind:

Sadly, this list may change due to the extreme violence in Chicago. Some of these names may be removed due to homicide or drug overdose.

Chicago Rappers Now Deceased (2023)

Unfortunately, many young and talented rappers from Chicago lose their lives due to senseless gun and gang-related violence.

Tragically, some of the rappers and entertainers killed from gun violence in Chicago include: OTF Nunu, FBG Duck, King Von, L’A Capone, Lil Jeff, CantGetRight, Lil Marc, Lil Mister, Lil Jojo, Young Pappy, Blood Money, Brick, and many more.

OTF Nunu was killed at 21 years old.
OTF Nunu was killed at 21 years old.

Deceased Drill Rappers

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.

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.

Fredo Santana with Lil Reese.

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.

Fredo Santana.

Lil Jojo

Joseph Coleman, better known as ‘Lil Jojo’, was shot to death during a drive-by shooting on September 4th, 2012.

Lil Jojo is of of the most infamous Gangster Disciples who started the bloody against the Black Disciples in drill music.

Lil Jojo.

Lil Mister

Tragically, Lil Mister (Montana), who’s real name is Antwon Fields, sustained a bullet wound to the head on March 15, 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 Lil Durk gave him about dealing with beef.

Lil Mister.

Unfortunately, Antwon was taken to the University of Chicago Medical Center, where he was later pronounced dead.

Facts about Lil Mister

  • Lil Durk and Montana are actually cousins.
  • Most famous 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.

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.


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.”

Dooski The Man.

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

Lil Marc.

Marc Campbell was a rapper from Chicago’s South Side as well as a gang member from 051 Young Money, a Mickey Cobra set of the Gangster Disciples.

Lil Marc was gunned down on Friday March 28, 2014 while waiting at a bus stop in Washington Park.

View D.rose’s deleted video from the Lil Marc hit.


Capo.Capo, was a talented 22-year-old rapper associated with Chief Keef’s Glo Gang.

Sadly Capo was shot and killed on Saturday, July 11, before being being rushed to the hospital where he was pronounced dead from gunshot wounds.

Young Pappy

Young Pappy.

Shaquon Thomas, also known as ‘Young Pappy’, was murdered at only 20 years old due to gang violence.

Young Pappy was one of the leaders of PBG (Poor Bear Gang),  a faction of the Insane Cutthroat Gangsters, are a subset of the notorious Gangster Disciples street gang.

Lil Jeff

Lil Jeff.
Lil Jeff.

Jeffery Morgan, also known as Lil Jeff, was a member of Fly Boy Gang and best friends with Lil Jay.

Lil Jeff and Lil Jay rapped together in the song, “Gunplay.”

Sadly, the 21-year-old budding rap star was murdered at a house party on Mother’s Day in 2013.



Our List Of The Best Rappers from Chicago

Additionally, check out our list of the best rappers from Chicago. Our list includes not only drill rappers, but simply the most influential entertainers from Chi-Town.

Furthermore, even though Kanye west was an easy choice, how could you not include Chance the rapper and Twista among the top 5?

Top 10 Chicago Rappers.
  • Kanye West.
  • Chance the Rapper.
  • Twista.
  • Common.
  • Lupe Fiasco.
  • Lil Durk.
  • Chief Keef.
  • Lil Jay.
  • Lil Jojo.
  • G Herbo.