Preferring to try for a path of music rather than sharecropper life, Sutherland played music whenever the opportunity presented itself in the 1920s and 1930s. He began to play with Theodore Harris early on who, in his estimation, was the finest fiddle player in the area. As he put it, "Yeah, he could really play it. There wasn’t no maybe about it. He’s the best fiddle player that ever went through here.”
By the 30s, the economic turmoil of the time wreaked its havoc, and musical work dried up for Sutherland. On top of this, he also had a child in the mid-30s, which also pulled him away from music. After also a brief stint as a prison labourer, Sutherland moved to Chicago with an aim to provide more income for his family. That reportedly led him to being away from his home area for over 37 years before he came back. During that time, he was able to earn enough to purchase his own house, with new neighbors such as Clyde Maxwell. It's in this new community (although still near his birthplace) that Alan Lomax and Worth Long travelled to in order to find and record him.