In February 1990, Thomas Pynchon releases Vineland, his first novel since the momentous Gravity's Rainbow 17 years prior. The novel focuses on the teenage daughter of a 1960s counterculture radical, trying to come to understand her parents' past and the world she has inherited amid the relentless pursuit of an FBI agent. Simultaneous with this release, set just down the road, is the film Flashback, in which a legendary hippie has been caught after going underground for twenty years, and the young FBI agent tasked with transporting the man instead has to grapple with the reality of his parents' culture. My guest, Geoff Shullenberger, lecturer at New York University and writer of his online project Outsider Theory, sees these two as not just a look at the past, but prescient visions of our present moment as well.