Thomas Pynchon’s treatment of sex and gender is full of apparent simplicities multiply undermined and rewritten, much of which rewriting seems prompted by changes in the evolving context of American culture’s treatment of sex and gender. From V. (1963) onward we can see Pynchon revising the 1950s misogyny that his very earliest work – like Minstrel Island, a libretto he cowrote in 1958 – had reproduced comparatively unambiguously. Minstrel Island sets an outcast band of artists and bohemians (male apart from “Whore” and “Sailmaker”) against IBM, here to regulate the mavericks out of existence in the name of “Big Mother Machine.” The leader of the IBM colonists is “Broad,” a young “career woman” who relies on a computerized translation machine to grasp the concept of love. Whore suggests that seducing Broad will be the way to halt the invasion, since “[s]omeday I’ll have to tell you about women. We’re all the same underneath.” Critics like Robert Holton and Molly Hite read Pynchon’s early work in terms of Philip Wylie’s A Generation of Vipers (1943), whose paranoia about emasculation by oppressive mother figures grounds its entire account of mid-war US culture. Minstrel Island, like the published short story “Low Lands” (1960), adopts this vision belatedly and uncritically in the manner of Ken Kesey’s One Flew Over the Cuckoo’s Nest (1962). What most sets Minstrel Island apart from Pynchon’s subsequent novels, however, is its essentially uncritical presentation of its male protagonist. “Hero,” seen through Broad’s eyes, is perhaps more of a caricature than her: “She is struck by something in her – an old note of a new feeling. She sees his handsome face, his air of freedom. And she is [sic] feels deep in her, for a moment, a sense of envy, of desire […] Hero seems to be full of compassion and pit [sic] for her, for he is a man with full understanding.” Between the abandonment of Minstrel Island and the completion of V., though, Pynchon’s sense of what might make a male protagonist compelling changed.