Winning Boy is one of the most significant characters in The Piano Lesson by August Wilson. Boy Willie wants to sell the piano but he doesn’t understand why she can’t get rid of it. Winning Boy’s story about the piano in his life is significant to the play for Boy Willie and the readers to understand what goes on behind Berniece’s head when she wants to keep it. Winning Boy compares the piano as the burden he carries within himself. He presents himself as a successful musician, however in reality he isn’t happy with his life. He compares the piano to his life of drinks, women, and his career. He explains in the beginning, his life was fun and he enjoyed every bit of it however he soon realized that everything he was doing and living for got