In the 1990s and early 2000s he established himself as a mainstay on the independent Chicago folk and alternative country scene before moving to Brooklyn in 2003.

[1] After playing in a high-school speed metal band with Rob Lloyd named Crystal Meth Death, Mills turned his attention to country and folk music.

[3] Mills released his first EPs in 1996 and 1997, and signed to Chicago indie label Sugar Free Records in 1998.

In 2005 Mills signed with Brooklyn indie label Ernest Jenning Record Co. and released The Wall to Wall Sessions, an album recorded and mixed entirely live to 2-track tape.

In 2009, the track "Such a Beautiful Thing" from Living In the Aftermath was featured on the popular television show Criminal Minds in the episode "Cradle To The Grave".