In 1904 the Premier of the Australian state of Victoria, Thomas Bent, expressed outrage at the way in which Australian Prime Minister George Reid had been depicted in a poster on advertising hoardings in the capital city, Melbourne. Although long forgotten, the resulting controversy—and this chapter’s analysis of this—presents a fascinating case study about the way in which responses to caricature offer insight into broader social and political developments. Australia’s fourth prime minister, George Reid, had a distinctive relationship with caricature: his rotund and instantly recognisable physical features and strong personality made him a cartoonist’s dream subject. The medium in which caricature is presented was also important. In 1904 the ridicule “public men” were expected to endure as legitimate political commentary had a different standard from that applying to other media, such as advertising. Above all, the line drawn between acceptable and unacceptable caricature was then, as it remains, subjective and dependent upon social and political context. The 1904 caricature controversy occurred in a society overly mindful of the decorum associated with public office in the first decade of nationhood. But it also allows greater insight in understanding more recent caricature controversies, especially the 2012 controversy surrounding caricatures of Prime Minister Julia Gillard. At the same time as there were important differences (the most significant being the gender of the prime minister), remarkable similarities help connect past and contemporary controversies in illuminating fashion.