Despite the critical consensus that a major part of David Foster Wallace’s project was to challenge the paradigms of postmodernism, there is an assumption that, when it comes to therapy, Wallace did little more than tell the same postmodern jokes. By focusing on Wallace’s engagement with other writers who have also written about therapy, I situate Wallace’s work in the context of a much larger turn in contemporary literature toward novels with more in-depth therapist characters. My discussion of Wallace’s influences includes the usual postmodern suspects, whose parodic tradition Wallace apparently champions, but I am especially interested in the unacknowledged influence of Sylvia Plath, whose work’s more generous treatment of therapists is quite at odds with her contemporaries and is, therefore, a more vital source for Wallace’s own