“Sheer Playfulness and Deadly Seriousness are my closest friends,” Philip Roth once said. This wry comment perfectly encapsulates the characteristic use of comedy and irony in his work; though his writing can be situated within a larger history of comic authors, his tragicomic style is immediately identifiable as his own, and has become part of his literary legacy. This chapter discusses Roth’s unique brand of humor, defining its iterations and tracing the different ways it is employed in some of his most notable works.