Upchurch became popular primarily as a comedian, creating videos on various platforms to garner support and fans.

[1] He released an extended play, Cheatham County, in 2015, followed by a full-length album, Heart of America, in 2016.

33 in the Top Country Albums chart with 3,700 copies sold, while Son of the South debuted at No.

[5] Upchurch's fifth studio album, King of Dixie, was released on November 10, 2017, and features 19 tracks.

Later that year, he released Parachute on September 24, followed by a collaboration album with Adam Calhoun entitled Hooligan on November 25.