Oprah Winfrey’s CBS TV interview with Meghan Markle, Duchess of Sussex, drew a great deal of public attention. Conducted against the background of much speculation in the U.K. tabloid press about the nature of the relationship between the Sussexes and the remainder of the British Royal Family, it was watched live by an audience of over 17 million in the U.S. and over 14 million in the U.K., with extracts carried on many TV news bulletins. In addition, it attracted a great deal of press, broadcasting and social media commentary. Audiences in the U.S. and the U.K., however, were divided in their reactions. In the U.S. sympathy for Meghan Markle was heightened, whereas in the U.K. audiences—especially older audiences—were less sympathetic. Overall, however, the interview was regarded as a showcase for Oprah’s empathetic interviewing style which was widely admired by commentators. This chapter considers particular features of Winfrey’s style and examines how she contrives against a background of pre-existing tabloid gossip to provide Markle with the discursive space to offer her own insider, alternative account of what was taking place ‘backstage’, in private. Amidst what might be called Markle’s ‘counter-gossiping response’, her revelation about concerns within the Royal Family regarding the skin colour of her future child with Prince Harry became news, prompting allegations of racism: the personal realm of gossip became political.