My choice would be Henry Roth's 1934 novel, Call It Sleep, which is quite possibly the most subtle and comprehensive literary work addressing the American Jewish immigration experience. As with any truly "classic" work, Call It Sleep can be read (and has been) in sharply contrasting ways. It can be seen as a celebration of multilingualism and ethnic pluralism, as a Bildungsroman, as a masterpiece of urban modernism, as a meditation on the Oedipal dynamics of the immigrant family, as an expression of Jewish longing for the gentile world, and as a cautionary tale about the effects of jettisoning Jewish tradition in an all-out embrace of American freedom. Whereas countless modern Jewish works express some measure of ambivalence about categories such as tradition and modernity, Roth's novel could be more properly called "multivalent": it expresses a number of distinct viewpoints, each one seemingly with great conviction. For instance, the traditional rabbi is depicted as a cruel and ignorant brute, but the Jewish textual tradition (in this case the Parsha to Jethro) is valorized insofar as it offers the young hero a solution to his deepest anxieties—as well as a paradigm for approaching God.
A seminar devoted to Call It Sleep could identify its range of perspectives on Jewish modernity and American urban experience, while also raising fundamental hermeneutical questions about whether and how a definitive "reading" of the text might be possible at all. Various methodological approaches could also be introduced. A unit on intertextuality could focus on its dialogue with James Joyce and T. S. Eliot and with Christian and Jewish readings of the Book of Isaiah. A unit on language could consider Roth's depiction of Yiddish as crystal-clear English, while also exploring the contrast between the broken English of the characters and the often exquisitely lyrical English of the third-person narrator. A unit on reception history could consider the dramatic resurgence of interest in the novel among second-generation American Jewish intellectuals in the early 1960s and, indeed, its position as a cornerstone in the emerging canon of Jewish American literature.