Schopenhauer singles out Kant's theory of the sublime for high praise, calling it ‘by far the most excellent thing in the Critique of Aesthetic Judgement’, yet, in his main discussion of the sublime, he ridicules Kant's explanation as being in the grip of scholastic metaphysics. My first aim in this paper is to sort out Schopenhauer's apparently conflicted appraisal of Kant's theory of the sublime. Next, based on his Nachlaß, close readings of published texts and especially of his account of the experience of tragic drama, I offer a reconstruction of Schopenhauer's theory of the sublime which understands it – against prevailing scholarly views – as a transformation of rather than as a real departure from the Kantian explanation. Finally, I suggest that my interpretation of Schopenhauer's theory of the sublime has far-reaching consequences for a proper understanding of his views on freedom.