Whereas the nineteenth century worshipped Shakespeare, towards 1900 his image became tarnished, also in fiction. Oscar Wilde carefully broached the question of Shakespeare’s sexual orientation in a story about his supposed infatuation with a boy actor. Made innocuous by replacing the boy actor by a stage-struck girl dressed up as a boy, this topic became a popular template for romantic plots about Shakespeare. Besides, Wilde opened up Shakespeare’s sex life, as the source of his inspiration, as a subject for later authors, including James Joyce. Likewise, George Bernard Shaw raised the issue of Shakespeare’s class consciousness, which gave rise to representations of Shakespeare as a snob, a sycophant, or a capitalist exploiter. Finally, the idea that the Dark Lady of the sonnets had been non-Caucasian led to fictions in which Shakespeare is blamed either for having an interracial affair to begin with, or for exploiting her in a misogynous and racist way. The chapter also traces the way in which Wilde’s use of a modern frame story was imitated by some later authors to soften their criticism of Shakespeare, by foregrounding the tendency of modern critics to project their own concerns onto Shakespeare’s works and life.