His second album Big Fish Theory was released in 2017. Staples has released the mixtapes Shyne Coldchain Vol. 1 in 2011, Winter in Prague (with Michael Uzowuru) in 2012, Stolen Youth (with Larry Fisherman) in 2013, and Shyne Coldchain II in 2014. His EP Hell Can Wait was released in 2014 and reached #7 on the US Rap chart and his EP Prima Donna was released in 2016 and reached #5 on the US Rap chart. Staples has collaborated with several other artists including Earl Sweatshirt, Gorillaz, Flume, and more.