Chief Keef’s career started like many other artist from Chicago, by uploading songs and videos to the website Youtube. Some of his most popular videos in the beginning of his career were “3Hunna” , “Bang” , and what is probably his most successful video to date “I Don’t Like”. After releasing “I don’t like”, fellow Chicago rapper Kanye West did a remix of the song which included numerous other artist such a Pusha T, Jadakiss, Big Sean and Chief Keef. The remix was equally successful as the original and is considered to have raised Chief Keef’s popularity.
After numerous successful Youtube videos, an inevitable war started over what label would get to sign Chief Keef, the bidding war included labels such as Young Jeezy’s CTE World and others. When all was done, Chief Keef would end up signing with Interscope Records due to the fact he was given his own record label Glory Boyz Entertainment(GBE) which would be partly owned by Interscope Records. Though there’s no official word on how much the deal is worth, most claim the deal is valued at six million dollars for three albums. The deal contains a clause which states if Chief Kief’s debut LP fail to sell 250,000 album by 12/2013, Interscope has the right to end the deal. Chief Keef’s debut LP titled ‘Finally Rich’ was released on the 18th of December, 2012. The album included numerous guest rappers such as Wiz Khalifa, Rick Ross, Young Jeezy, 50 Cent as well as some of his fellow GBE members. A couple of months after releasing his first album, the world learned via Twitter that Chief Keef was officially a member of the record label ‘1017 Bricksquad owned by Gucci Mane.
Like many of his fellow rap artists, Chief Keef is no stranger to the legal system. He was arrested in 2011 for manufacturing and distributing heroin, and was placed on house arrest for his criminal act. During that same year Chief Keef would again be arrested on different charges, this time, for resisting arrest. In December 2011, after leaving his Grandmother’s home, he was spotted by a cop while having his hand over his waistband. When the cop stopped to question him, Keef fled and dropped the coat he was wearing, the cops gave chase, and ended firing multiple shots at Chief Keef, which all missed. The officers claimed while chasing Chief Keef, he constantly turned around to point a gun at them. Chief Keef was apprehended about a block away from the initial site of the confrontation and the police recovered a loaded handgun. Chief Keef was charged with aggravated unlawful use of a weapon and three counts of aggravated assault with a firearm on a police officer. Chief Keef was also charged with a misdemeanor for resisting arrest. After being held in the Cook County Juvenile Detention Center, he was sentenced to house arrest under his Grandmother’s supervision.
Chief Keef had a long standing feud with Joseph 'Lil JoJo' Coleman, a rapper from Chicago and a member of the criminal gang ‘Gangster Disciples’, which has a story of beefing with Chief Keef’s gang the ‘Black Disciples’. The two made numerous songs dissing each other. Lil Jojo was gunned down on September 4th, 2012 while riding a bike belonging to one of his friends. Witnesses claim a man in a Ford Taurus fired multiples shots at Lil Jojo , he soon fell and died on the scene. Police claim they had recovered a weapon on Lil Jojo, but he never had the opportunity to fire back since he was shot from the back. After his death, Chief Keef tweeted ‘Its Sad Cuz Dat Nigga jojo Wanted to Be Jus Like Us #LMAO’. Chief Keef later added another tweet claiming his Twitter account was hacked “my twitter has been hacked I think I'm making a new one dumb hating *ss people #DontWannaSeeAYougN*ggaShine”. Chief Keef was looked at as a person of interest due to his feud with Lil Jojo by many, including Lil Jojo’s mother, whom has openly admitted that she’s certain that Chief Keef ordered the murder of her son.
While on parole, Chief Keef was part of interview which took place on a shooting range, while filming the interview, Chief Keef fired a firearm which was a violation of his parole. Upon seeing the video, the Cook County prosecutors recommended that the judge incarcerate Chief Keef for violating his parole. The courts demanded that ‘PitchFork Media’, the website that did the interview, turn over the videos of the interview. On January 15, 2013 Cozart was arrested after the juvenile court judge agreed that Chief Keef violated his parole by doing the gun range interview, which led to Chief Keef being sentenced to two months in the juvenile detention facility. Keef served his two months sentenced, and was release on March 14, 2013.
Chief Keef would once again be arrested on May 20, 2013 in DeKalb County in Atlanta, Georgia for allegedly smoking weed in public, as well as disorderly conduct. He was released on the same day the incident took place. Barely a week after being arrested for dope, Chief Keef would once again be arrested for doing 110 mph in a zone with a speed limit of 55 mph in Chicago. He went to court for the violation on June 17, and ended up pleading guilty for speeding. He was ordered to pay a fine of $531, complete 60 hours of community service, undergo random drug tests, and was placed on 18 month probation.
Sometime in June 2012, a Chicago rapper that goes by the name Rhymefest posted a blog attacking Chief Keef’s image, he wrote on a blog post that "Chief Keef is a 'bomb,' he represents the senseless savagery that white people see when the news speaks of Chicago violence," he turn some of the blame to the record labels that employs the likes of Chief Keef by saying "A bomb has no responsibility or blame, it does what it was created to do: DESTROY! Notice, no one is talking about the real culprits, the bomb maker or the pilot who is deploying this deadly force (labels, radio stations). It's easier to blame the bomb...who is bank rolling this operation and why? This could only be described as an opportunity for this young man if he was receiving artist development, responsible mentorship and counseling for his obvious trauma...major record labels always put million dollar life insurance policies on artist of this nature so that they get paid one way or the other."
Rhymefest also went on to say “(Chief Keef) is a spokesman for the Prison Industrial Complex. Every corporation is expected to grow at least 4% each quarter, many prisons are privately owned with stock being traded on the open market. If these corporations were to do commercials, jingles and promotions who would they hire? You got it, most of the main stream rappers we salivate over like Rick Ross the former correctional officer turned Drug Lord Boss rapper. Waka Flocka Flame gang bang “GO HARD IN THE PAINT” and Chief Keef the newest lottery pick in the 'Get paid to destroy young minds, like we destroyed yours' sweepstakes." Rhymefest would later clarify his former comments by posting ““I don't have anything against any particular kind of music. My problem is the imbalance of the music that we get,” There’s no formal reply from Chief Keef on Rhymefest’s comments.
During September of 2012, Lupe Fiasco, a Chicago native said "Chief Keef scares me" during an interview with 92 Q Jams, he also claims that violence plaguing Chicago is “the culture that (Chief Keef) represents”. Soon after Lupe’s comments aired, a tweet came from Chief Keef stating “Lupe fiasco a hoe *ss ni*a And wen I see him I'ma smack him like da lil b*tch he is #300”. Lupe would later replied to Chief Keef’s comments with multiple tweets of his own “i love u lil bruh @chiefkeef...i really really do from the bottom of my f*cking heart. I know that street shit like the back of my hand.” “I'm trying to DO better @chiefkeef as we all should. We were born with no expectations to make it. born in the hood, live there die there..” I cant go 4 that @chiefkeef & i cant let the people i love, including you my n*gga, go 4 that either. We kings not fucking savages and goons” Chief Keef later twitted that his account was hacked “my twitter has been hacked I think I'm making a new one dumb hating *ss people #DontWannaSeeAYougN*ggaShine”. Lupe Fiasco would then tweet that his next album would probably be his last.
On September 15, 2012 a lewd photo of Chief Keef started circulating over the internet. The photo which was uploaded by Chief Keef on Instagram, depicts the rapper being given oral sex by an unknown female companion. Chief Keef’s actions would result in him being banned by twitter for violating their terms of service, which bans nude photographs. Chief Keef has opened a new account since the incident.
Chief Keef went at it with Katy Perry after she twitted “Hate Being Sober” a song by Chief Keef made her have "serious doubt for the world". Chief Keef responded by tweeting "Dat b*tch Katy Perry Can Suck Skin Off Of my D*ck," "Ill Smack The Sh*t out her ?" "New Song Katy Perry Coming Soon". Katy Perry later apologized to Chief Keef for the comments, writing on Twitter “Mr. Keef! I’m sorry if I offended you. I heard a lot of people guesting on the song & didn’t even know it was you in particular. Actually…,” the pop star tweeted. “I’m a fan of your “Don’t Like” video tbh. I was really just having a general opinion on our generations desire to be constantly intoxicated.”. When Chief Keef was questioned on the subject after the apology, he claimed he “don’t give a f*ck”.
Chief Keef also had a feud with DC rapper Shy Glizzy, the beef’s origin is unknown, however, numerous people believed it’s due to Chief Keef doing a track with DC rapper ‘Fat Trel’ whom Shy Glizzy had problems with, and also because Shy Glizzy sang over one of Chief Keef’s tracks. Shy Glizzy attacked Chief Keef on a track titled “3 Milli’ which he sang over Chief Keef’s “3hunna’ beat. Chief Keef also released a track attacking Shy Glizzy titled “Cashing Out”.
King Louie is rumored to be affiliated with the criminal gang known as the Gangster Disciples, and his music crew is called Man Up Band Up (MUBU). During the ‘Windy City Drift Tour’ a scuffle took place between the MUBU crew and GBE crew which includes artists such as Chief Keef, Lil Reese and Ballout. During the scuffle one of the fans managed to snatch a chain from Ballout which he Ironically robbed Soulja Boy of. After the scuffle, a man from Davenport name Cameron Oliver posted on facebook that he was in possession of Soulja’s chain “No Play Play We Here… Contact Soulja Boy Tell em We got his sh*t….” King Louie later posted on Instagram what many are considering a warning to Ballout “#ITsOnlySoLongFakeThugsCanPretend,” he also posted “Naw dis was chain ballbout took from soulja boy and a fan took it from from @balloutbayyy b*tch he betta stay out the city”
In 2013, Lil Durk was arrested on gun charges and his bail was set at $100,000. Lil Durk needed $10,000 in order to be release from jail, Chief Keef didn't give him the money. Upon being release from jail a series of tweet from both Chief Keef and Lil Durk ignited a beef between the two friends. The first tweet was sent out by Chief Keef whom tweeted "What happen to OTF? U ain't rocking with it?", Lil Durk soon responded tweeted "Dats like praying on DA weak lol we got DA city #OTF300." The feud didn't top there, Lil Durk then slammed Chief Keef for not providing his bail money by tweeting “Ion respect no n*gga that leave they homies n jail". Chief Keef only made matters worse when he tweeted he just bought a vehicle that cost $10,000 which was the exact amount of money Lil Durk needed for bail “Jus Bought A 2013 4 wheeler Fa 10thousand,”
In October 2014, it was revealed that Chief Keef was dropped from Interscope Records. Though this came as a surprise to some, many were anticipating Interscope's decision. For starters Chief Keef's mixtape and sophomore record were continuously pushed back with no explanation given to fans, then there was all the legal drama surrounding Chief Keef. Many critics believe Interscope came to the conclusion that Chief Keef was no longer an asset but rather a liability on their side, hence their decision to drop him.