Oprah's Hawaii Home

A strong connection to her past drew Oprah to The Waterboy, a 1946 masterpiece by the famous American painter Thomas Hart Benton. It's one of her most recent purchases and one of the most dramatic. "He's like someone I knew growing up," she says of the painting's plaid-shirted, straw-hatted young man. "I bought him because I loved him." Now in the dining room, his presence powerful and alive, The Waterboy is like a welcome old friend.

On the 18th-century English dresser, which still retains its original blue paint, a cluster of multicolored French Jaspé pottery pitchers stands between two brass candlesticks housed in 19th-century glass hurricanes.