Throughout the 20th century, cartoons relentlessly appeared in all sorts of newspapers, evidence of the immense cultural impact of illustrative satire long before the era of television. Many events were recorded in print, such as the Great War, the 1916 Easter Rising, women’s suffrage, the Second World War, and the Cold War. This chapter uses Gombrich’s ‘6 point filter’ for cartoon analysis to present both case studies and longer- term trends. Case studies include pioneering Irish satire in The Lepracaun, and British football cartoons used to present the perspectives of the working - class British soldier from 1914 to 1918. The authors analyse several trends over time, including increased ‘creative acerbity’, for instance during ‘The Troubles’ in Northern Ireland, through to a greater personalisation of issues and use of a celebrity approach, often as propaganda during the Cold War and Vietnam. Findings from the analysis of over a thousand images point to an increase in derivative amateur cartoons, which is construed as a democratic tool for expression.