The author attempts to show that philosophy and literature can – in an equally radical, destructive and yet productive way – intervene in the running of our conceptual apparatus, schemes of imagination and patterns of interpretation. He focuses on three philosophical and two literary examples of this kind: 1) In the Phenomenology of Spirit, Hegel describes, in a most dynamic (and “physically” evocative) way, the movement performed by thought which strives to articulate a speculative content in the traditional subject-predicate form (based on a fixed substance-attribute opposition). 2) The externalist thought experiments (H. Putnam, T. Burge and others) have an equally radical effect: they subvert our intuitions concerning the contents of thoughts and communicative acts and the “natural” assumption that these contents are located in our heads. 3) The Gricean semantics with its well-known regresses leads to the conclusion that any act of “meaning something by something” expands (in its intentional structure) in infinitum: this is a radical challenge for our intuitions concerning the nature of communicative attitudes and communicative acts. 4) The narrator in Beckett’s Trilogy (in particular in The Unnamable) describes his mind as a space for the interventions of other, more assertive and more efficient, minds. Moreover, he concludes that even this thought should be ascribed to them, the same holds for this conclusion etc. in infinitum: in this way, the narrator’s subject collapses in an infinite regress. This corresponds to the externalist revision of the internal nature of our thought (cf. 2) as well as the Gricean regresses affecting any attempts to identify the position from which we “mean something by something” (cf. 3). The resulting collapse of the referential role of the first person pronoun, as well as other examples of Beckettian destruction of basic language functions, provide a literary analogy to Hegel’s revision of the traditional sentence form (cf. 3). Another contribution to this confrontation is to be found in Borges’ Pierre Menard story.