This chapter explores the connotations of a period of cartooning history during which (according to a number of researchers), American caricature reached its heyday. During the Civil War (1861–1865), popular cartoons—increasingly complex in composition and mature in skill—reflected the most difficult period of American history in a light which was at the same time humorous and tragic. Artists such as Thomas Nast, John McClellan, Frank Bellew, and Adalbert John Volck worked on illustrated periodicals such as Harper’s Weekly, Frank Leslie’s Illustrated Newspaper, and Vanity Fair in the North/Union and the Southern Illustrated News and Southern Punch in the South/Confederacy. In the conditions of a military conflict, caricature turned out to be effective as a weapon of war. Its goal was to make fun of the enemy, present him in a comic way, convince the warring parties of the rightness of their own cause, mobilise society on achieving victory, and give vent to feelings of anger and frustration. In the North, the image of the enemy—“Johnny the Rebel”—was constructed in order to incite hatred towards the Southerners, while in the South, the image of the “Damned Yankee” was created, with both relying on developed stereotypes, as well as on the collective unconscious and archetypes associated with religious views and historical roots.