Cleveland relies on energy supplements to keep himself awake in order to work overtime and earn enough vacation time to go on a Spring Break cruise with his family. But when his energy pill addiction forces him into rehab and his desperate attempt to escape to the cruise liner goes wrong, he finds himself held hostage by pirates threatening the safety of those aboard the ship, including his own family.

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.