[5] He learned to play the guitar,[5] and listened to traveling bluesmen from other parts of the South, as well as on the radio.

Drawing inspiration from Blind Boy Fuller, he began singing and playing guitar at local parties and other community events by the time he was in his mid-teens.

Holeman relocated to Durham, North Carolina, in 1954, where he played with the pianist Fris Holloway.

[4] During his working lifetime, Holeman had full-time employment as a construction worker, and music was a part-time pursuit.

[2] A song Holeman wrote, "Chapel Hill Boogie", was featured on the 2007 Grammy Award–nominated album 10 Days Out: Blues from the Backroads, recorded by Kenny Wayne Shepherd.