Known as "The Dixie Dewdrop", Macon was known for his chin whiskers, plug hat, gold teeth, and gates-ajar collar; he gained regional fame as a vaudeville performer in the early 1920s before becoming the first star of the Grand Ole Opry in the latter half of the decade.

"[1] Macon's polished stage presence and lively personality have made him one of the most enduring figures of early country music.

The hotel became a center for Macon and his growing musical interests, and was frequented by artists and troupers traveling along vaudeville circuit and circus acts.

Often, when Macon was driving along with his mules, hauling freight and produce, he would entertain people by singing and playing the banjo at various stops along the way.

[12] In 1925, Macon and Harkreader added "Dancing Bob" Bradford, a buck dancer to their act, Their tours on the Loew's circuit now included comedy, buck-dancing and old time music.

[13] On November 6, 1925, Macon and Harkreader performed at the Ryman Auditorium—the future home of the Grand Ole Opry— in a benefit for the Nashville police force.

[21] His funeral was visited by more than five thousand people and his pallbearers were George D. Hay, Kirk McGee, Roy Acuff, and Bill Monroe.

His son Dorris and several bandmates (often including Sam and Kirk McGee) made sporadic appearances on the Grand Ole Opry as the Fruit Jar Drinkers until the early 1980s.

Bandmate Kirk McGee later described Macon's personality as a never-ending performance— "All day long, from morning till midnight, it was a show.

[24] Macon was famous for his outrageous and funny performances, whether playing on the Vaudeville stage, at school and community socials, or at the Grand Ole Opry.

Macon peppered his performances with jokes and comedic monologues, and often engaged in witty repartee with sidemen such as Sam McGee and Sid Harkreader.

[2][24] Macon's favorite tunes included "A Soldier's Joy", "Bully of the Town", "The Arkansas Traveler", and "Sail Away, Ladies".

[2][26] Macon claimed to have learned the song "Rock About My Saro Jane" from black stevedores working along the Cumberland River in the 1880s.

[2] The song "Buddy Won't You Roll Down the Line" was inspired by the Coal Creek War, an East Tennessee labor uprising in the 1890s.

[27] In the song "From Earth to Heaven", Macon describes his days hauling goods between Woodbury and Murfreesboro for his shipping company.