Roth does not hesitate to interrogate and skewer many elements of American identity and politics (and identity politics) in his work; nevertheless, certain characters maintain an investment in particular values and ideologies. One of these is the notion of American individualism, which is embraced by characters ranging from Neil Klugman in Goodbye, Columbus to Seymour Levov in American Pastoral. This chapter will situate some of Roth’s key works in the larger context of an American individualist ethic, also addressing the way his works respond to changing notions of American exceptionalism.