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English critic Matthew Arnold considered Mark Twain’s work symptomatic of a cultural thinness in America, where basic liberty, equality, and prosperity might be in reach of ordinary people, but where nothing would prod genuine cultural development. Twain might be able to entertain a “philistine” middle class, Arnold implied, but ultimately, he could not contribute anything “interesting” to human civilization. Twain responded both directly (in speeches) and obliquely (in his novels) to this criticism of his brand of humor and of American democratic culture. After comparing and evaluating Arnold’s and Twain’s arguments, I discuss how this nineteenth-century debate about democratic humor can inform our current political climate, in which attempts at humor are brought under close political scrutiny and judged (often crudely and without humor) through populist or elitist lenses.