Alfred Hitchcock's Vertigo is one of the most acclaimed films of all times, recognized by scores of critics, film theorists, and film historians as a pivotal work in both film history and film theory. By now, Vertigo is so deeply embedded in film theory that it is almost impossible to read it without referencing the cinematic lexicon of scopophilia, fetishism, voyeurism, the sadistic male gaze, objectification of the female body, mental images, relational images, thought cinema, the imaginary Real, the symbolic Real, and the “Real Real.” This essay traces how critical readings of Vertigo reflect pivotal debates in film theory, particularly psychoanalytic readings of gender politics that question the status of the “real,” leading to the crisis of representation and of our understanding of subjectivity. Rather than evaluate which particular interpretation is better grounded than the others, this essay demonstrates how competing readings of Vertigo end up ungrounding the very theoretical apparatuses behind them. It provides a history of the theoretical treatment of Vertigo but focuses mainly on the ongoing debates between Žižekian and Deleuzian readings of the film. The author argues that Vertigo is potentially many films, possibly about many of the issues attributed to it, but one that does not simply represent theoretical and philosophical points. It is a film that both transforms with new theoretical readings or filmic offshoots and questions these readings by offering other possible relations and critical reflections.