This dissertation argues that Victor Hugo’s penultimate novel, L’homme qui rit (1896), redefines and complexifies romantic irony into what I call a poetics of cruel humor, that is, a paradoxical form of dark humor removed from the comic force and situated at the intersection of cruelty and extreme irony. I show that this specific transfiguration of the vis comica is steeped in the theory of the Grotesque, which Hugo began to develop in his 1827 Préface de Cromwell. Chapter one works as a springboard for the following chapters. It recontextualizes the discussion of the Hugolian poetics of laughter within the author’s philosophical and metaphysical perspective, tracing the genesis of cruel humor to the author’s broader concerns about the phenomenology of the real. Chapter two explores Paul Leni’s The Man Who Laughs (1928). I consider how this hybrid adaptation infused with both expressionist and Hollywoodian aesthetics resonates with Hugo’s theory of the Grotesque. I analyze the many mise en abyme techniques to demonstrate how this film transfigures the spectacle of cruelty displayed on screen into a poetics of cruelty that reaches beyond the screen to implicate not only the audience, but also the cinematic act of creation. Chapter three studies Jean Kerchbron’s faithful and extremely realistic TV series, L’homme qui rit (1971). Looking at the interplay between Hugo’s complex notion of “chimérisme” and the different forms of cynicism in the series, I underline the fundamental ironic mechanism at work behind the cynical surface and show that this double register that shapes Kerchbron’s hybrid televisual language, also offers an interesting variation of romantic irony. Chapter four explores Jean-Pierre Améris’s L’Homme qui rit (2012). I show that the film exploits the hybrid characteristics of Hugo’s original plot through variations on the Freudian theory of the “narcissistic scar,” which it transfigures by transposing its meaning onto the cinematic experience itself. Ultimately, this dissertation contributes to the continuous effort to rehabilitate Hugo’s masterpiece and demonstrates that Hugo was indeed the precursor of an uncanny form of romantic irony which did not die out but rather grew and developed new branches.