In ‘Comedy and Finitude’, chapter 10 of Ethics— Politics— Subjectivity, Simon Critchley explains that, in the context of post-Kantian philosophy, art has taken the place that religion and metaphysics once had, of providing models and tools for grappling with existential concerns. In ‘Comedy and Finitude’, Critchley specifically discusses tragedy, and explains how it has represented an influence on the problem of death, of the possibility of our own impossibility, in many modern thinkers. Critchley criticizes tragedy as a model for resolving this tension, and instead presents comedy as a preferable solution. In this paper, I will try to expand Critchley’s by analogizing dramatic tragedy with Francis Bacon’s portraiture, and Pop art with Harpo Marx’s comedic performance.