Arnold "Doc" Wiley had a vaudeville duo with his sister, vocalist Irene Wiley. They moved to Chicago from their hometown Helena, AK during the 1920s. They first recorded as a duo for Okeh in 1926, when they cut songs including "Dear Old Companion." They returned to the studios in late 1927 for Brunswick, and again in 1931, when they recorded the song "Jumpin' Judy Blues," among others for Columbia. In addition to his collaboration with his sister, Doc Wiley backed Margaret Whitmire for Brunswick in the late '20s, and recorded solo tunes including Windy City" and "Spider In Your Dumpling" for Brunswick and Paramount.