This chapter discusses comedy and humor as distinct but related aesthetic phenomena in the philosophies of G.W.F. Hegel and other German Idealists and Romanticists. It traces the history of comedy as an aesthetic category and connects it to important German theorists such as Immanuel Kant and Friedrich Schiller. It analyzes the significance of comedy throughout Hegel’s philosophical trajectory, considering it in comparison to tragedy and its position in Hegel’s systematic view. It argues that what is proper to comedy is a destructive power capable of dissolving the inessential, aiming at a renewed conciliation and the emergence of a higher dimension. It briefly addresses the notion in the German context of the time beyond Hegel. The chapter then turns to humor as a relatively new aesthetic category in Hegel’s time, influenced by Lawrence Sterne’s writings and signaling a gentle amusement at humans’ foibles: a distinction brought out in Hegel’s differentiation between subjective and objective humor. Humor’s ability to articulate humans’ position in relation to the infinite is traced through Jean Paul Richter, K.W.F. Solger, Novalis, and Friedrich Schlegel. The chapter concludes with an indication of humor’s continuing importance for philosophers such as Søren Kierkegaard and Friedrich Nietzsche.