The purpose of this paper is to explore the relationship between offence and humour in advertising. One only needs to watch a stand up comic to appreciate that these two emotions are often closely linked. The relationship is also becoming increasingly evident in advertising as brands compete to create a modern, entertaining and witty personality. But when and why does an advertisement move from being funny to being offensive? This study firstly looks at the literature on both humour and offense in advertising and brings them together to establish areas of commonality. This knowledge is then used to analyse advertisements that were complained about to the ASA in 2009 which contained both humour and offense. These cases are examined to find out how offence is created and the type of humour that is creating this offence. The implications of the findings for practitioners and regulatory bodies are then discussed