This chapter examines the taboo-breaking humour of Chappelle's Show, The Sarah Silverman Programme and Four Lions. With particular attention to the different ways in which these texts clearly define and then breach social boundaries and taboos for the purpose of humour, this chapter considers how provocative humour intentionally and tastelessly intervenes in socially charged conversations in a manner that is explicitly coded as insensitive and quite possibly offensive to a hypothetical audience.