This article begins by arguing that the ‘madness’ of Antonin Artaud is either fetishised or resisted, depending on the disciplinary angle from which one works. It proposes an alternative approach to the study of Artaud, which might avoid such pitfalls by reading Artaud’s work as performative philosophy or a philosophy of performance. The approach is defined by the principle of ‘working with’, rather than working on, a literary or philosophical figure. The second part of the article works, or philosophises, with (...) Artaud, reading his work on the ‘Theatre of Cruelty’ alongside Immanuel Kant’s work on judgment from the third Critique. It explores the Kantian distinction between determining and reflective judgment, extending reflective judgment into what I call anarchic reflection. To do so, the article elucidates the conceptual relation between actuality, entropy, an-archy, cruelty and sublimity, defining anarchic reflection as an unintentional and/or intentional crisis of the judgment or krisis of Form that opens the possibility of its transformation. (shrink)