Cleveland is labeled "The Whitest Man in America" after he wins a dance competition for the chance to attend a pop sensation's concert. Unable to shake off his new reputation, Cleveland is determined to understand his roots and where he came from. Everything starts to make sense when he is reunited with his former nanny Barbara, a high class woman with a taste for refined culture. But even though Cleveland's nanny influenced many of his interests growing up, Cleveland finally learns that happiness comes from being comfortable in your own skin.