Hamnet Shakespeare has only ever been famous posthumously. While his iconic father and his proximity to the tragedy Hamlet would have guaranteed him some mention in the history books, his premature death elevated him to celebrity status. Hamnet died at the age of 11 in 1596, but the last decade has seen this dead child grace the page, stage, and screen. William Shakespeare’s only son is the star of the one-boy play Hamnet (Kidd and Moukarzel, 2017), where he addresses the audience from a hellmouth and ponders existential questions, including “To be or not to be”. In contrast, Hamnet is barely even a minor character in the BBC sitcom Upstart Crow, but his death in series 3 (2018), although off-screen, is impactful. The show even pays homage to the boy with an obituary in the episode’s closing credits. Branagh’s All is True (2018), a star-studded heritage biopic, foregrounds Hamnet as a ghost, as raison d’etre for his father’s writing, and as the victim of a family ‘whodunnit’. While in Maggie O’Farrell’s novel Hamnet (2020), the eponymous boy-hero succeeds in cheating death by exchanging his life for his twin sister’s, and is then resurrected in his father’s most famous play. Drawing on Shakespearean drama and modern popular culture, these texts position Hamnet’s death as challenging in a variety of ways. In this paper, I examine how Hamnet’s death is rendered difficult by his symbolism (the boy is a figure of innocence, vulnerability, futurity) and by Shakespeare’s dual status as literary idol and parent. I explore too how these texts challenge the scant historical records on Hamnet by granting him a voice as well as the agency to question, check, make demands of, and change the audience, and even challenge the colossus that is his father’s legacy.