This episode explores the history and evolution of political cartoons, tracing their development from religious satire in the 16th century to their modern forms. Against the backdrop of the printing press's invention, early examples like Martin Luther's woodcut prints emerged as powerful political statements, bypassing literacy barriers. More significantly, the discussion highlights the contributions of key figures like William Hogarth, considered the grandfather of political cartoons, and James Gillray, its father, who used exaggeration and satire to critique power. As the discussion pivoted to the American context, the episode features Benjamin Franklin's "Join or Die" cartoon and Thomas Nast's impactful work, which famously helped bring down Boss Tweed. In contrast to the earlier era, the episode also examines the role of political cartoons in World War II, featuring the works of Dr. Seuss and Bill Mauldin, and the impact of censorship and changing media landscapes on the profession. Finally, the episode concludes by discussing the legacy of political cartoons, their enduring power, and their evolution into modern memes, highlighting the ongoing debate about freedom of expression and the changing role of political cartoonists in the digital age.