Born in New Madrid, Missouri,[2] Wiley ran away from home as a youth to join a Chinese circus where he performed as an acrobat.
He later returned to his family and moved to Helena, Arkansas, where he joined the local black ragtime scene as a singer, dancer, and pianist where he played with such figures as Roosevelt Sykes, William Ezell and Jesse Bell.
Their material was ragtime-influenced and received good reviews; however, Bertha disliked touring so when Arnold decided to move to Chicago in 1925 she remained behind.
Lee was also a political activist and he and Wiley became members of the Communist Party USA and were involved with various causes, particularly civil rights.
He had formed a Rhythm and Blues trio similar to those of Johnny Moore, Charles Brown, Slim Gaillard and Nat King Cole including a guitar or vibraphone and saxophone.
This trio made a series of singles including "How Long Blues" (originally by Leroy Carr and Scrapper Blackwell), "Wild Cat Boogie", "Every Day of the Week" (originally by Big Joe Turner), "I'm in Love Again" (by Lonnie Johnson) and "Chain Gang Blues".