Madonna — David Letterman
One of the most memorable interviews in the history of talk shows is Madonna's appearance on David Letterman's show in 1994. In this widely discussed interview, it appeared that Letterman was attempting to goad Madonna into displaying her usual flashy and controversial persona, but Madonna wasn't willing to oblige.
Despite Letterman's persistent efforts to encourage her to kiss a random audience member and engage provocatively, Madonna firmly shut down his attempts. She confronted him directly, asking, "Why are you so obsessed with my [love] life?" Her response highlighted the host's futile attempts to stir up needless drama during the interview, making it a defining moment in the annals of celebrity talk shows.
