The three men were involved in the music publishing business in St. Louis, Missouri. About 1914 they joined a band and went to Los Angeles. They passed their traveling time making up verses to a traditional tune. When they returned to St. Louis the trio went their separate ways. Art Gillham remained in St. Louis, Billy Smythe went to Louisville, Smythe's brother-in-law Scott Middleton went to Chicago. In 1915 Billy Smythe published their musings as "Hesitation Blues" but not crediting Art Gillham.
A dispute over the credits was resolved a few years later when Art Gillham and Billy Smythe began writing other songs as a team with the sheet music stating "by the writers of Hesitation Blues".
The song was recorded for Edison Records in 1919 by Al Bernard and exists as a Blue Amberol cylinder recording and as an Edison Diamond Disc matrix recording. Audio files of this recording are preserved at the Cylinder Digitization and Preservation Project of the University of California Santa Barbara. 
Art Gillham performed the song on radio and in February, 1925 recorded it for Columbia Records as one of the first electrical recordings. The song was republished in 1926 giving credit to the three writers. The 1926 publication was a different arrangement with different lyrics added to the 1915 publication.
The 1964 version by the Holy Modal Rounders featured the first use of the term "psychedelic" in popular music in the verse "Got my psycho-delic feet, in my psycho-delic shoes, I believe lord and mama got the psycho-delic blues, tell me how long do I have tell to wait, or can I get you now, or must I hesitay-ay-ay-ate". The original sleeve notes (as reproduced in the CD notes) state "A Charlie Poole hit. Charlie Poole and the North Carolina Ramblers recorded an incredible number of songs that are personal favorites of mine."