Born in 1934, Bobby Headden began boxing at an early age. He is a native of Charleston, S.C. but boxed out of Charlotte for most of his career. Headden lost very few matches. He won a total of 65 and lost two amateur bouts and one professional match. His amateur losses were as a representative of the Carolinas at the National Golden Gloves in New York City, and in an intercity meet in Chicago. Headden made such an impression in New York he was chosen to box for an eastern team against a western team in Chicago. He trained under Lou Kemp in Charlotte and his brother-in-law, Doc Deneaux, in Charleston. Headden was a workman-like boxer with power in both hands. A flyweight, he always wore a deadpan expression in the ring.
Headden spent his working life in the trucking industry. Beginning as a teen, he started out as a checker and was a driver for 40 years. Headden and his wife Barbara are the parents of three children.