This chapter traces how popular and critical models of humour align with liberal discourses of freedom and reasonableness through an analysis of Jon Stewart and Stephen Colbert's "Rally to Restore Sanity and/or Fear," held in Washington D.C. in October 2010. Tracing this understanding of humour through a range of recent humour theory, this chapter argues that the model of humour as a form of dissent is both ascendant and reductive, and over-determines the political work of humour without sufficient attention to the actual aesthetic manifestation of humour and the politics thereof.