Mostly blind from infancy, Grayson is chiefly remembered for a series of sides recorded with guitarist Henry Whitter between 1927 and 1930 that would later influence numerous country, bluegrass, and rock musicians.
Grayson wrote much of his own material, but was also instrumental in adapting several traditional Appalachian ballads to fiddle and guitar formats.
His music has been recorded or performed by musicians such as Bob Dylan, Doc Watson, Mick Jagger, the Kingston Trio, and dozens of bluegrass artists, including the Stanley Brothers and Mac Wiseman.
's uncle, James Grayson (1833–1901), was a Union Army officer who helped organize an anti-Confederate uprising in Carter County, Tennessee at the outbreak of the American Civil War and later aided in the capture of legendary North Carolina fugitive Tom Dula.
As he was unable to work due to his near-blindness, he began playing at various small venues and dances around Johnson County to make money.
"Train 45" was derived from the banjo tune "Reuben," and "Joking Henry" was probably influenced by the folk song "Frankie and Johnnie."
He learned "Nine Pound Hammer" from fellow fiddler Charlie Bowman (who had picked it up from an African-American musician), and his version of "Short Life of Trouble" resembles Clarence Ashley's recording during the same period.
[1] Ralph Stanley has recorded Grayson's song "Little Maggie, with a dram glass in her hand" multiple times.