In this paper I offer a selective, systematic rather than historical account of Merleau-Ponty's highly complex relation to classical German philosophy, focussing on issues which bear on the question of his relation to transcendentalism and naturalism. I argue that the concerns which define his project in Phenomenology of Perception are fundamentally those of transcendental philosophy, and that Merleau-Ponty's disagreements with Kant, and the position he arrives at in The Visible and the Invisible, are helpfully viewed in light of (1) issues which Merleau-Ponty identifies as raised by Kant's Critique of the Power of Judgement, and (2) Schelling's conversion of Kantian idealism into a Real-Idealismus. Finally I address the question of whether, and on what basis, Merleau-Ponty's claim to have surpassed systematic philosophy can be defended.