This chapter proposes a new interpretation of two short stories included in David Foster Wallace’s 2004 collection Oblivion: ‘Incarnations of Burned Children’ and ‘Another Pioneer’. The close reading of the two texts highlights three features previously neglected. First of all, the similarities between the two main characters (children who die a violent death) and a relevant number of cross-references invite us to consider them a diptych well past their initial surface differences. Secondly, both stories examine the philosophical issue of the contested relationship between self-awareness and linguistic communication: whereas in ‘Incarnations of Burned Children’ the baby ends up dead because it screams in pain without being able to tell his parents where it hurts, in ‘Another Pioneer’ the inscrutability of the child savant is the result of an excess of rational thought and analytical language that segregate him from the village community. Thirdly, these stories show in an exemplary manner Wallace’s position between philosophy and literature: issues concerning self-awareness, the limits of human language, and the potential of thought (probably influenced by contemporary philosophers such as Nagel, Rorty, and Derrida) flow into a specific narrative form, thereby demonstrating that Wallace is not a philosopher disguised as a narrator but a writer unable to be fully philosophical (in the traditional sense) as he offers the reader questions with ambiguous answers and no exit.