This chapter argues that Dave Chappelle, Affion Crocket, and the duo Jordan Peele and Keegan-Michael Key have all fallen victim to the black comedic Conundrum of excessively physical comedy. These comedians testify not only to the problems associated with representations of the black male body, but also highlight the lack of strong female comediennes headlining television sketch comedy shows. This chapter also notes, however, that each of these comedians has produced satire that conveys substantive social commentary.