This introductory chapter introduces the themes of the volume Cartoon Conflicts: Contemporary Controversies and Historical Precedents and places them in the broader context of contemporary debates over freedom of speech and respectful communication practice. It advances the simple case for cartoons’ importance, especially as historical sources providing a window into the past. Cartoons shape and reflect national(ist) and other identities; as such they often become focal points for debates on democracy, censorship, offense, and legislation; and technological changes have not only transformed the methods of cartoon production but also influenced the distribution and consumption of cartoons, leading to shifts in the cartoon’s form and function over time. As expressions of opinion, commentary on events as they happen, cartoons will inevitably take sides and cause offense to one or other “side” in a debate. That in the twenty-first century this offense is more often associated with the manner in which targets of caricature are depicted, rather than the political or ideological message being advanced, says much about the “identity” politics of the 2000s, 2010s, and 2020s. But does this new need to be fair and careful, eschew the tried-and-true method of stereotype, and take steps to avoid causing offense (however this is constructed) undermine the very purpose and effectiveness of cartooning? Is this the “end of history” for the cartoon as a striking weapon of political discourse?