While he is best known for his Jeeves and Bertie Wooster stories, P.G. Wodehouse was a prolific writer who penned many other novels, stories, and musical comedy libretti, the latter of which played an enormous role in the development of American musical theater. This collection re-examines Wodehouse in the context of recent scholarship on the middlebrow, attending to his self-conscious relationship to the literary marketplace and his role in moving musical comedy away from vaudeville’s lowbrow associations towards the sophistication of the Wodehouse style. The focus on the middlebrow creates a critical context for serious critical consideration of Wodehouse’s linguistic playfulness and his depictions of social class within England. The contributors explore Wodehouse’s fiction and libretti in reference to philosophy, depictions of masculinity, World War I Britain, the periodical market, ideas of Englishness, and cultural phenomena such as men’s fashion, food culture, and popular songwriting. Taken together, the essays draw attention to the arbitrary divide between high- and middlebrow culture and make a case for Wodehouse as a writer whose games with language are in keeping with modernist experimentation with artistic expression.