John Dee Holeman was born in Orange County, North Carolina in 1929, and has been playing the blues since he was around 14 years old. He credits Blind Boy Fuller as the man who taught him to play, however he never met Fuller himself. He learned by listening to Fuller's records and by playing with musicians who had learned directly from Fuller. Holeman is a magnificent guitarist, and uses both the Piedmont and Texas guitar styles in his playing.

Holeman was awarded a National Heritage Fellowship in 1988 and a North Carolina Folk Heritage Award in 1994. He is recently retired from being a heavy machine operator, and currently still tours at home and abroad. He has toured in the U.S., Europe, and Asia. Holeman used to accompany his performances by buckdancing, but after two strokes no longer attempts dancing, and some days has a difficult time walking. Oddly enough, Holeman says he is not a professional musician. "Nope-don't get paid like one either," he once said in an interview. "Got talked into playing a little guitar at the Eno (Eno River Festival) a few years back and have been doing it ever since.