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Drawing from emo, indie rock, avant electronica, and more, Chicago-based indie rapper Serengeti earned a reputation as being an immensely prolific writer, evidenced by his barrage of long-players, all imbued with his oddball personality and abstract rhymes. Born David Cohn, the whimsical MC spent most his youth in the Chicago suburbs and began writing rap lyrics around the same time he moved into the city at age 16. His eccentric inclinations developed under his divorced parents' two schools of thought: his mother was a political activist and self-styled socialist, but his father had an upper-middle-class way of life. When Cohn went off to college, he met fellow classmate DJ Crucial, who had similar hip-hop ambitions. Crucial eventually founded F5 Records and issued Serengeti's 2003 debut, Dirty Flamingo. It was the first of practically a dozen albums that he released through various independent labels within the next few years. Noteworthy standouts were the experimental rock-leaning Gasoline Rainbow (2006), released via MF Grimm's Day by Day imprint, and the imaginative, blogosphere-approved Dennehy (2006) on Bonafyde. Signed to Audio 8, Serengeti collaborated with glitch-hop producer Polyphonic for Don't Give Up (2007), but then revisited Dennehy a year later, issuing an expanded version. On the title track, Serengeti invented a fictional character named Kenny Dennis, who became a staple for future albums, including 2012's Kenny Dennis EP, 2013's Kenny Dennis LP, and 2014's Kenny Dennis III.