In this paper I explore Walter Benjamin’s complex thoughts about the concept of experience to illuminate a central paradox when thinking about madness. This paradox concerns the need to hold together constellations of concepts that appear to be diametrically opposed. On the one hand there is the realm of the psychopathological; a psychiatric thinking of madness as mental illness that refers to suffering, loss of existence, and dysfunction. On the other hand, there is a thinking about madness as a diverse and different experience, as possibility, illumination, and difference. Benjamin’s writings on experience can be particularly fertile here because he acknowledges the contradictions in experience, at certain points emphasising the loss of experience and at other points focussing on the possibilities of a new experience even within a destruction of experience. I will explore three aspects of Benjamin’s reflections on experience and their relationship to an experience of psychosis; the loss of experience in modernity and the possibilities that lie within such a loss, the turn towards the object in Benjamin’s account of experience, and finally the concept of the limit-experience. I conclude by considering Benjamin’s idea of the dialectical image and apply this idea to the experience of madness.