Early life (1995–2010)

Chief Keef was born Keith Farrelle Cozart in Chicago, Illinois, to Lolita Carter who was 15 and unwed. He is named after his deceased uncle, Keith Carter, who was known as "Big Keef". He lived at the Parkway Garden Homes, locally known as O-Block, located in the Washington Park neighborhood on the city's South Side, a stronghold for the Black Disciples street gang of which Chief Keef is a member.

Chief Keef has been estranged from his biological father, Alfonso Cozart, since he was a minor. His legal guardian was his grandmother with whom he lived in Chicago. He began rapping at five years old using his mother's karaoke machine and tapes to record his music. During his childhood, Chief Keef attended Dulles Elementary School and the Banner School, a therapeutic day school. He dropped out of Dyett High School at 15.

Early years, Finally Rich, and subsequent mixtapes (2011–2013)

In 2011, Chief Keef first attracted local attention from Chicago's South Side community with his mixtapes, The Glory Road and Bang. In December, he was arrested for firing a gun from his car in Chicago's Washington Park neighborhood; he was placed under house arrest at his grandmother's residence for 30 days, followed by another 30 days of home confinement. While under house arrest, he posted several videos to his YouTube account of music focusing on Chicago's hip hop subgenre drill.

Keef's song "I Don't Like" became a hit in Chicago. A local party promoter called it "the perfect Chicago song because '****** just hate everything out here'". It caught Kanye West's attention, and he remixed the song with rappers Pusha T, Jadakiss and Big Sean. As a result, Keef "suddenly shot up out of obscurity".

In the summer of 2012, Chief Keef was the subject of a bidding war among record labels wishing to sign him, including Young Jeezy's CTE World. While 2012 proved to be a relatively quiet year in terms of his musical output, Chief Keef began the year by signing with Interscope Records. In a separate deal he was promised his own label imprint, Glory Boyz Entertainment (GBE). The deal was worth $6,000,000 over a three album layout, with an additional $440,000 advance to establish GBE.

The deal gave Interscope the right to pull out of the contract if Chief Keef's debut album Finally Rich, released on December 18, 2012, had failed to sell 250,000 copies by December 2013. Featured guests on the album include rappers: 50 Cent, Wiz Khalifa, Young Jeezy, Rick Ross and his fellow Glory Boyz member Lil Reese. In May 2013 he signed with 1017 Brick Squad Records.

Chief Keef is featured on "Hold My Liquor", the fifth track on Kanye West's album, Yeezus, released on June 18, 2013. Keef's contributions to the track were praised by musician Lou Reed who said, "'Hold My Liquor' is just heartbreaking, and particularly coming from where it's coming from – listen to that incredibly poignant hook from a tough guy like Chief Keef, wow."

On his 18th birthday, August 15, 2013, Chief Keef celebrated by releasing the mixtape Bang, Pt. 2. It was highly anticipated as the first project following his debut album, but received a mixed to negative critical response. On October 12, 2013, another mixtape, Almighty Sosa, was released. Like Bang, Pt. 2, Almighty So also received mixed to negative critical reviews. After serving his October 2013 jail term, he began working on his second studio album and a biopic.

Nobody and Bang 3 (2014–2016)

Chief Keef began experimenting with producing his music in 2014. In January, Chief Keef announced he was working on a new mixtape entitled Bang 3. In February, he unveiled the cover art to his upcoming mixtape Back From The Dead 2 the sequel to his critically acclaimed mixtape, Back From The Dead. During February, Chief Keef said his former lean addiction and bad mixing contributed to the lack of quality music on his two mixtape projects Bang Pt. 2 and Almighty So and that he was disappointed in both projects.

Later in February 2014, he announced an EP before his second studio album Bang 3, entitled Bang 4, as a preview. The following day, Fredo Santana announced he and Chief Keef were going to release an album collaboration. In March, Keef released the first official single from Bang 3 entitled "**** Rehab" featuring his fellow Glo Gang artist and cousin Mario "Blood Money" Hess. This marked Hess's final recording before his death on April 9, 2014. On March 14 Chief Keef released the official music video for "**** Rehab". Although Interscope executive Larry Jackson announced that Bang 3 would be released on June 10, it was delayed again.

In October 2014, Chief Keef was dropped by Interscope Records. He confirmed via Twitter that every project he had planned, including the release of the long-awaited Bang 3, would still be released. Despite being set for a December 2014 release, Bang 3 did not materialize. Chief Keef's mixtapes, Mansion Musick set for a November 28 release, and Thot Breakers set to release on February 14, 2015, were not released as announced. However, he was successful in releasing Big Gucci Sosa, a 12-track collaborative mixtape, with Gucci Mane, as well as Back From the Dead 2, which was made available for digital download from iTunes. Chief Keef self-produced 16 of the 20 songs on the mixtape.

In November, he announced Nobody, a "Glo Producer album" that featured guest vocals by Kanye West and Tadoe. It was set to be released on December 2, but appeared on December 16. The album's title track was noted for being one of Keef's more emotionally driven tracks.

On February 18, 2015, Chief Keef released Sorry 4 the Weight, a 20-track mixtape. The mixtape was largely a solo effort, featuring only Andy Milonakis and Glo Gang labelmate, Benji Glo. In 2015, his track "Faneto" was slowly building momentum since its October 2014 release. On April 24, 2015, Chief Keef announced his next album, titled The Cozart, saying it would be released soon. He signed with FilmOn Music, a division of media tycoon Alki David, in May 2015.

On July 11, 2015, Marvin Carr, better known by his stage name Capo, a longtime member of Chief Keef's Glo Gang label, was shot and killed in a drive-by shooting in Chicago. After killing Capo, the driver of the vehicle reportedly struck a stroller holding 13-month-old Dillan Harris killing him instantly. Chief Keef announced on Twitter he would be holding a free benefit concert as a tribute to Capo and encouraged concertgoers to donate to the Harris family. He also announced the formation of the Stop the Violence Now Foundation, in an attempt to decrease crime in Chicago. Because of outstanding warrants in Illinois, Keef was scheduled to attend the concert via hologram from a sound stage in Beverly Hills.

The concert, organized by HologramUSA and FilmOn Music, was planned to be held in Chicago's Redmoon Theater. It faced a series of delays after Chicago mayor Rahm Emanuel's office claimed Chief Keef was "an unacceptable role model" and that his music promoted violence. Chief Keef's representatives then worked out an arrangement with promoters of Craze Fest in Hammond, Indiana, to hold the concert there. Chief Keef's hologram made a plea for peace in Chicago saying, "Stop the violence, stop nonsense, stop the killing. Let the kids grow up", before performing "I Don't Like".

Fearing the concert was a threat to public safety, Hammond mayor Thomas McDermott, Jr. had the city's police department shut down the generators powering Chief Keef's hologram. McDermott was quoted as saying, "I know nothing about Chief Keef. All I'd heard was he has a lot of songs about gangs and shooting people — a history that's anti-cop, pro-gang and pro-drug use. He's been basically outlawed in Chicago, and we're not going to let [him] circumvent Mayor Emanuel by going next door."

Dedication, Glotoven and Almighty So 2 (2016–present)

In March 2016, Chief Keef tweeted that he was retiring