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Finn Pollard explores P. G. Wodehouse’s early twentieth-century fiction and charts the evolution of the famous author’s portrayals of the United States and its people from his initial use of common archetypes to much more complicated themes and character relationships, including Anglo-American friendships as well as romantic entanglements. Pollard delves into the period influences that contributed to this evolution, including the boys’ school story, the nature of London theatre, and Anglo-American romance novels, and seeks to illuminate why Wodehouse’s British and American characters mingled with increasing ease, were at times treated as interchangeable, and asserted a mutually positive relationship. Ultimately, this exploration of popular literature suggests readers in both countries were increasingly exposed to a new, influential, and warmer narrative of Anglo-American relations in the period preceding the Great War.