He attended school in Brown, Kentucky. Massey worked for nearly seventy years on a local farm for the same family, who eventually deeded him his house in gratitude for his service. After his wife died in 1955 he began to create sculptures and paintings. In 1984 he had to stop farming and made his art full-time.

Massey worked in wood, foil, “as found” objects and paint. He made miniature pieces of furniture. He was best know for his fanciful birdhouses with their wingless birds and painted sides.

He died of complications from burns suffered in a fire after his house and art burned.