Furry did not begin as a musician, But rather worked as a comedian, sold corn medicine and liniment oils, or did vaudeville sketches, often in blackface. During these travels, he continued to develop his guitar skills and probably learned how to play bottleneck style. He was also exposed to many of the best-known Blues musicians of the time; people such as, Memphis Minnie, Texas Alexander, Blind Lemon Jefferson, and often he would play alongside noted guitarist Jim Jackson.

His guitar work began to pay off for him and he had no problem making money. But, in 1916, he found himself attempting to jump a freight train outside of Du Quoin, Illinois. He didn't need to ride the rails in this manner, as he had about $200 - $300 in his pocket at the time and could've purchased a ticket, but Furry wanted to save the cost and while trying to jump the train, he caught his foot in a coupling and was struck, losing his leg. He spent the next month in a railroad hospital in Carbondale. Illinois, recuperating from the injury. He was later fitted with an artificial leg that took him nearly a year to become comfortable with wearing.

It was too much of a hardship to try to work as an itinerant musician with an artificial leg, so Lewis returned to Memphis. He took up performing on street corners with the local jug bands, often with popular favorites such as Will Shade's Memphis Jug Band and Gus Cannon's Jug Stompers. But, Furry made his living more often doing a variety of odd jobs including freight hauling from riverboats, yard work or delivering groceries. In 1923, he took a position with the Memphis Sanitation Department, sweeping streets around Beale; a job that he would hold for the next 43 years.