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Milsap was born with a congenital defect that left him blind. He lived with his grandparents until age 6 when he was placed in the State School for the Blind in Raleigh, North Carolina. Milsap showed musical aptitude at an early age. The school stressed classical music training but he preferred country, gospel and rhythm-and-blues. He released his first single, Total Disaster, in 1963 at the age of twenty.