By necessity, immigrants must think, act, and live experimentally when they arrive at their new destination. Given that the essay also possesses an experimental quality, it is unsurprising to find that in the United States – often called the land of immigration – the essayistic canon includes a vast corpus of writing by immigrants. Indeed, the dual or multiple identity of an immigrant-essayist is one of the most common in American writing. This chapter is concerned with a particular group of such immigrant-essayists: those who arrived in the United States as a result of exile from Germany. It focuses particularly on Hans Richter, Hannah Arendt, Theodor W. Adorno, Bertolt Brecht, Ernst Kantorowicz, Thomas Mann, and Herbert Marcuse (as well as his student Angela Davis) who – like countless other artists, scholars, authors, directors, and other intellectuals – fled to the United States from war, persecution, and precarity in Europe during the 1930s and ’40s. The final section explores the works of Christa Wolf, an author who grew up in socialist East Germany and whose visits to the United States before and after the fall of the Iron Curtain strongly influenced her essayistic writing.