The paper argues that Pynchon’s publishing career underscores a biographical divide in Pynchon’s consciousness between his commitment to marginalized, anti-orthodox modes of being, particularly those valued by the counterculture that emerged in the 1960s in the US, and the value of classical, to use a term from Pynchon’s Ford Foundation statement, modes of being, not simply in his fiction but in his letters and other biographical documents that have come to light.