This week, Chief Keef caused a stir by releasing two tracks with Andy Milonakis, a comedian who'd formerly rapped alongside RiFF RAFF and Dirt Nasty in the group Three Loco. The man who came up as the poster boy for Chicago's violent drill scene was chilling out a bit and embracing humor with these tracks, or so it seemed. In actuality, the Milonakis co-sign was just the latest in a long line of unexpected and seemingly out-of-character moves by the dude born Keith Cozart. 

Getting a jump-start on his rap career by using mom's karaoke machine to record his first rhymes at age 5, Cozart grew up quick on the Chicago's notorious Southside, showing up on his first mixtape at age 14 and fathering his first child at 16. By 17, he had signed a $6 million record deal with Interscope, which would eventually crumble in Fall 2014, leading to Keef parting ways with the label. Since then, his music has taken a turn away from the radio-ready bombast of songs like "Don't Like" and gotten much more unorthodox. Keef's now dropping loosies left and right, not to mention the three projects he's released since last October, and honing on his production chops. 

Breaking Keef's career into four parts -- his pre-Interscope days, the Finally Rich era, his last days on the label, and everything else up until yesterday's Sorry 4 The Weight -- we'll take you through the evolution of his music.