This article presents a cultural and media analysis of failure in its dialectical relationship with success, emphasizing the relative, frequently changeable and highly context-sensitive nature of the notion of failure. Aiming to offer a broad overview of the questions and based on a survey of the available literature, it opens on a general discussion of the status of failure in modern art and literature. It then proposes a general framework describing the three main aspects of the contemporary “fail better” aesthetics: antihero (content), antistyle (form), antitext (discursive framing). In a third and last part, the various tools and hypotheses are tested with a case study: three works by comics artist Daniel Clowes.