Driftwood used that unique guitar throughout his career and noted that its neck was made from a fence rail, its sides from an old ox yoke, and the head and bottom from the headboard of his grandmother's bed.

Driftwood's first album, Newly Discovered Early American Folk Songs, received good reviews but did not sell particularly well.

Driftwood left Arkansas for Nashville and became popular by his appearances on programs including the Grand Ole Opry,[4] Ozark Jubilee, and Louisiana Hayride.

After Horton's success, Driftwood performed at Carnegie Hall and at major American folk music festivals before returning home to Timbo, Arkansas in 1962.

[6] During his recording career Driftwood also won Grammy Awards for Wilderness Road, Songs of Billy Yank and Johnny Reb and Tennessee Stud.

Driftwood songs were recorded by Eddy Arnold, Johnny Cash, Hawkshaw Hawkins, Homer and Jethro (the parody "The Battle of Kookamonga"), Odetta, Doc Watson and others.

[7] For a time during the 1960s, Driftwood toured the United States and Europe with the Preservation Hall New Orleans jazz band, although as a separate act.

[6] Driftwood became involved with environmental issues when the United States Army Corps of Engineers planned to dam the Buffalo River.

He was also named to the Advisory Committee of the Kennedy Center for the Performing Arts in Washington, D.C.. Due to his extensive knowledge of folk music he was appointed as a musicologist for the National Geographic Society.