He is best remembered as the first performer to play on Nashville's Grand Ole Opry (then called the WSM Barn Dance), appearing with founder and host George D. Hay on the evening of November 28, 1925.
He likely learned a number of tunes (including "Flying Clouds", which he recorded in 1930) from veterans returning from the American Civil War (1861–1865), and his fiddle style always showed a strong Texas influence.
[3] Thompson returned to Tennessee a few years after the Dallas contest, this time settling near Hendersonville, a town located a few miles northeast of Nashville.
Being too old to farm, Thompson purchased a Ford truck which he outfitted with a makeshift camper, and he and Ella spent the next several years travelling around the state, performing at various fairs and other gatherings.
[3] In 1925, the National Life and Accident Insurance Company established WSM, the first radio station in Nashville that could reach a regional audience.
In September of that year, WSM began airing rural musicians from the Nashville area, namely Humphrey Bate, Sid Harkreader, and Uncle Dave Macon.
[3] During this period, Hay issued a challenge to Maine fiddler Mellie Dunham, who had recently captured first prize in a nationwide fiddle contest held by automobile magnate Henry Ford.
Thompson easily advanced through the early rounds to the contest's Tennessee state finals, which were held at the Ryman Auditorium in Nashville on the evening of January 19.
In the contest's regional finals in Louisville, Kentucky the following day, however, Thompson failed to place in the top three, being ousted by both Stephens and Claiborne and a South Indiana fiddler named W.H.