This essay examines how a literary genre called the character sketch shaped the ways Americans came to understand electoral representation as representative. Now little known but central to eighteenth- and early-nineteenth-century literary culture in the US and Britain, character sketches and a related aesthetic discourse about how to distinguish “well-drawn characters” from caricature helped to naturalize the notion that meaningful, legitimate representation should be grounded in clearly delineated categories and distinctions that were true to the “Laws of Nature and Nature’s God.” However, this aesthetic and political framework intersected uneasily with the early nineteenth century’s racially and economically diverse electoral public sphere. This public sphere was rife with fear that electoral “combinations” would so badly misrepresent the electorate that the United States would be functionally returned to tyranny. And these abstract fears often became entangled with the embodied discomfort genteel white men like Washington Irving experienced when “beer-barrel” politics brought them into contact with fellow voters whom they considered themselves naturally socially or racially distinct from. As a result, this paper shows, writing for and about early US elections—including Washington Irving’s “Rip Van Winkle” (1819), whose electoral plot is often overlooked—was imbued with a disconcerting sense of double vision. Only by recovering that double vision’s embodied and racialized electoral context can critics fully grapple with the aesthetic and political legacy of American literature’s uneasy foundations.