In this essay, I analyse some aspects of the transmediality operated by the British director T. Gilliam between Cervante’s Don Quichotte and his film The Man Who Killed Don Quixote (2018), with emphasis on the use of the Portuguese convent of Tomar. The complex and multifaceted architecture of this magnificent monumento, nowadays a UNESCO World Heritage Site, developed over several centuries, whose construction began in the 12th century and was successively extended until the 16th century, where T. Gilliam shoots an important part of the film (which largely corresponds to the stay of the Cervantes Quichotte and Sancho in the House of the Dukes), provides the ideal space for this director’s aesthetic and visual imagination. Which, by the way, does not fail to evoke what O. Welles had already done, namely in his use of Goya’s imagery. I conclude with what I consider to be a masterly use of the multi-purpose Tomar Convent in the construction of theatrical and carnivalised (Bakhtine concept) situations, extremes and distopics, of a Cervantine nature.