Standing ‘shoulder to shoulder’ with the United States is how Prime Minister Tony Blair liked to see himself during and after the 2003 Iraq war. That he and his government often, but by all means not always, ended up standing ‘shoulder to waist’ is only one of many aspects that characterised Anglo-American relations in the period between 9/11 and the end of Blair’s premiership in 2007. Both sides, however, were not left without benefits from their so-called ‘special relationship’. The often accurate, but in many instances also unjust and too shallow portrayal of Anglo-American relations in cartoons during the timeframe in question builds the main object of study of this paper. On the one hand the analysis focuses on the depiction of the relationship between and the opposing characters of Tony Blair and President George W. Bush, on the other hand the relation between the two leaders and the rest of the world as well as the role of the United Nations are discussed.