Since 1979, Holley has devoted his life to the practice of improvisational creativity. His art and music, born out of struggle, hardship, but perhaps more importantly, out of furious curiosity and biological necessity, has manifested itself in drawing, painting, sculpture, photography, performance, music, and filmmaking. 

Holley did not start making and performing music in a studio nor does his creative process mirror that of the typical musician. His music and lyrics are improvised on the spot and morph and evolve with every event, concert, and recording. In Holley’s original art environment, he would construct and deconstruct his visual works, repurposing their elements for new pieces. This often led to the transfer of individual narratives into the new work creating a cumulative composite image that has depth and purpose beyond its original singular meaning. The layers of sound in Holley’s music, likewise, are the result of decades of evolving experimentation.

Holley has released five critically acclaimed albums––Just Before Music, 2012; Keeping a Record of It, 2013; MITH, 2018; National Freedom, 2020; Broken Mirror: A Selfie Reflection (with Matthew E. White), 2021. His sixth album, Oh Me Oh My, produced by Jacknife Lee, which includes collaborations with Bon Iver, Michael Stipe (REM), Moor Mother, Sharon Van Etten, and Rokia Koné, comes out March 10, 2023, on Jagjaguwar.

He has toured extensively throughout the United States, Europe, Brazil, Australia, and New Zealand, and shared stages with Bon Iver, Animal Collective, Deerhunter, Bill Callahan, Saul Williams, Tinariwen, Daniel Lanois, and many others.