August Wilson has a lot to say about Wining Boy:
Wining Boy is fifty-six years old. Doaker's older brother, he tries to present the image of a successful musician and gambler, but his music, his clothes, and even his manner of presentation are ole. He is a man who looking back over his life continues to live it with an odd mixture of zest and sorrow. (2.2.1)
Yep, that pretty much sums up Wining Boy. He's spent his life drinking, gambling, and playing the piano. And that's still what he's doing. Wining Boy spends most of the play trying to get money from people so that he can go off and party.
Wining Boy does seem to regret his life a bit. He talks about how he's grown tired of all the whiskey, women, and piano playing. Wining Boy seems especially regretful when comes to his wife Cleotha, who kicked him out years ago. He says that, though he loved her, he couldn't quit his rambling ways.
Along with his brother, Doaker, Wining Boy also functions as a griot, or African storyteller. Just like the ancient griots, Wining Boy constantly tells stories of the family's histories and of things he's heard about on his travels. Wining Boy adds songs to the mix too. So, when he sits down at the piano to play the blues, he's not just passing the time – he's passing on a bit of African-American heritage.