With fiddler Leonard Rutherford, he formed a long touring partnership and a brief recording career in which they sang a number of popular and influential sides with Burnett on banjo or guitar.

Dick was also a skilful composer and folk poet of considerable skill; his "Man of Constant Sorrow" remains one of the most evocative country songs.

[3][4] As a teenager, then as a married man with a child, Dick Burnett worked extensively as a wheat thresher, logger, oil driller and oilfield tool fitter.

[2] Musicians in Wayne County could elicit small change from audiences drawn from people frequenting or passing through the Monticello Courthouse Square.

[1][3] To add further variety to his increasingly rich repertoire, Dick Burnett purchased novelty gadgets that made nonmusical noises.

[1][4] Around 1914, Burnett proposed to solve the problem of travelling as a blind man by employing teenaged Leonard Rutherford as sighted companion.

Their first trip together was to the nearby Laurel County Fair, then young Leonard spent more and more time with the older man, becoming a permanent companion when his parents died.

Burnett was not his only music teacher; he learned from other South Kentucky fiddlers, including the African American Cuje Bertram.

They appeared at the Renfro Valley Barn Dance, on radio stations in Cincinnati, and finally, they were some of the first old-time musicians to enter the recording studios.

Columbia Records had started its dedicated 3500-D series 1924 for the Old Familiar Tunes country market,[6] without many authentic Southern performers, but Columbia had some success with groups such as the north Georgia Skillet Lickers, the Virginia Blue Ridge Highballers, and the band of North Carolina's Charlie Poole.

Country-music historian Charles Wolfe considers that the success of these records encouraged Frank Walker to shift Columbia's emphasis from studio singers such as Vernon Dalhart to authentic southern artists.

One of these was rejected, so a take of "Cumberland Gap" was issued with a reverse recorded by Burnett and Moore with another fiddler, Charles Taylor.