In 2007, Serengeti released the first collaborative album with producer Polyphonic, titled Don't Give Up. The duo released their second collaborative album, Terradactyl, in 2009. In 2011, Serengeti released his solo album, Family & Friends, which was produced by Yoni Wolf and Owen Ashworth. Serengeti is a member of Sisyphus along with Son Lux and Sufjan Stevens.
The trio released Beak & Claw in 2012 and a self-titled album in 2014. In 2012, Serengeti released C.A.R., as well as Kenny Dennis EP. Kenny Dennis EP was Serengeti's first release chronicling the biography of his meta character "Kenny Dennis", a once-famous Gangsta rap artist navigating life after the peak of stardom. The EP was later ranked among the top 40 Hip Hop releases of 2012 by SPIN Magazine.
He followed this up with Kenny Dennis LP in 2013 and Kenny Dennis III in 2014. 2020 saw the well-received release of Ajai with collaborator Kenny Segal, a continuation of the Kenny Dennis canon. Cohn raps about the life of Ajai, a new character obsessed with Designer clothing and sneaker drops, who interacts with Dennis within the drop-collecting community.