Self proclaimed "art rap pioneer" Tim Holland (better known by his stage name Sole), is an experimental and indie hip-hop artist out of Portland, Maine. Sole got his start in hip-hop around the age of 15 in 1994, after pressing his very first vinyl with the money he had saved up working fast-food. Sole would appear as part of several abstract hip-hop collectives through the 1990s before co-founding his own record label Anticon and launchig his solo career with the release of the album "Bottle of Humans" in 2000.

Through-out much of the 2000s, Sole continued to develop his unique approach to abstract hip-hop with his signature styleless verse and stream of consciousness lyrical style as well as injecting his work with his strong sociopolitical beliefs and cynicism, garnering substantial notoriety with releases like "Selling Live Water" and "The New Human Is Illegal". By the later 2000s, Sole had met with and began a collaberative side-project with The Skyrider Band (as "Sole and The Skyrider Band") that has since become a continous project evolving alongside his solo work.

Soon after collaborating with The Skyrider Band, Sole's relationship with his label Anticon began to deteriorate, ending in a lawsuit for the rights to his own catalog. In the fallout, his future endeavors were qiuckly picked up and endorsed by indie hip-hop label Fake Four Inc.

Follwing this second wind for his career, Sole continued to evolve his style, easing away from the dense stream of consiousness lyricism and abstract music in favor of a more contemporary hip-hop style largely inspired by popular hip-hop acts in the mainstream, as well as incorporating more convential ryhme schemes to his lyrical approach with releases such as "Hello Cruel World" and "A Ruthless Criticism Of Everything Existing" in the early 2010s.