1988 (photo by Tom Pich)
Born in Hillsborough in 1929, at the age of six his family moved to a farm in northern Orange County. According to Holeman, “My father was Willy Holeman, and my mother was born Annie Obie near Roxboro, N.C. Her daddy moved to Hillsborough and ran a flour mill. James Obie was my uncle; there are still Obies in Hillsborough. I lived on the Sam Latta place at first – he was the High Sheriff. There were three sisters and one brother."
As a teenager, Holeman would go to Durham to play music during tobacco auction season; he also played house parties, pig-pickings, wood choppings, corn shuckings, country dances, and at "juke joints." He learned to play guitar from his uncle and cousin, and by listening to 78 rpm records by Blind Boy Fuller
. Played with Arthur Lyons and pianist Fris Holloway, among others. Holeman moved to Durham in 1954.
He died in Roxboro, NC at the age of 92.