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The Anatomy Lesson (1983) features Philip Roth’s most extensive fictional treatment of Commentary, the magazine of Jewish affairs founded in 1945 and patronized by the American Jewish Committee. Before Roth’s apparent break with Commentary in the wake of Irving Howe’s and Norman Podhoretz’s one-two punch to his career in the December 1972 issue, the magazine was part of Roth’s emerging sense of a distinctly American Jewish intellectual identity while helping him separate from what he perceived to be his own limiting origins. A reconsideration of Roth’s dealings with the magazine complicates the sharp distinction often made between Commentary’s sometimes romanticized history as a bastion of postwar, left liberalism in the 1940s and 1950s, on the one hand, and its more familiar iteration as a flagship publication of neoconservatism in the 1970s and 1980s, on the other. Turning to Roth’s fiction as an additional source of insight yields an aesthetic theory of fiction as a space for an analytical encounter with ambivalence.