Pickens was born in Holdenville, Oklahoma, the son of Grace Marcaline (née Molonson) and Thomas Boone Sibley Pickens. His father worked as an oil and mineral landman (rights leaser). During World War II, his mother ran the local Office of Price Administration, rationing gasoline and other goods in three counties. Pickens was the first child born via Caesarean section in the history of Holdenville hospital. His great-great-grandfather was politician Ezekiel Pickens, who was Lieutenant Governor of South Carolina.