His style of banjo playing, as well as his singing, is considered a unique combination of Appalachian folk music and African-American blues.

[2] He also recalled sneaking over to the African-American camps in Dorchester at night, where he first observed string bands playing at dances and parties.

He was enamoured of the bands' banjo players' preference for picking, having previously been exposed only to the "frailing" style of his siblings.

He learned much of his technique during this period from his brother Roscoe and an itinerant musician named Homer Crawford, both of whom shared Dock's preference for picking.

[3] The constantly moving mining camps were fraught with excess and violence, and Boggs was consistently engaging in drunken brawls that often left him or an opponent badly injured.

The stock market crash of 1929 and the subsequent Great Depression hit southern Appalachia particularly hard, and few people had the means to pay musicians to play at gatherings or buy records.

Seeger was delighted to learn that Boggs had recently repurchased a banjo and had been practicing the instrument for several months before his arrival.

His technique, which Seeger considered "a style possessed by no other recorded player,"[4] was adapted to fit previously unaccompanied mountain ballads.

Lee Hansucker, his brother-in-law, taught him various religious songs, including "O Death", "Little Black Train", "Prodigal Son", and "Calvary".

The song "Wise County Jail", written by Boggs in 1928, was inspired by an incident in which he had to flee to Kentucky, after attacking a lawman who tried to break up a party at which he was playing.