This paper forges links between early analytic philosophy and the posits of semiotics. I show that there are some striking and potentially quite important, but perhaps unrecognized, connections between three key concepts in Wittgenstein’s middle and later philosophy, namely, complex (Philosophical Grammar) , rule-following (Philosophical Investigations) , and language games (Philosophical Investigations) . This reveals the existence of a conceptual continuity between Wittgenstein’s “early” and “later” philosophy that can be applied to the analysis of the iterability of representation in computer-generated images. Methodologically, this paper clarifies to at least some degree, the nature, progress and promise of an approach to doing philosophy and semiotics from a modally modest perspectiv e that sees in the intellectual products of humanities, and not in unreflective empiricism, the future of scientific development. This hybrid, non-reductionist approach shows, among other things, that semiotic processes are encoded by specific types of complexes in computer-generated images that display iterability in time and space.