The semantically ambiguous nature of the sign and aspects of non-classicality of elementary matter as described by quantum theory show remarkable coherent analogy. We focus on how the ambiguous nature of the image, text and art work bears functional resemblance to the dynamics of contextuality, entanglement, superposition, collapse and decoherence as these phenomena are known in quantum theory. These quantumlike properties in linguistic signs have previously been identified in formal descritions of e.g. concept combinations and mental lexicon representations and have been reported on in the literature. In this approach the informationalized, communicated, mediatized conceptual configuration—of e.g. the art work—in the personal reflected mind behaves like a quantum state function in a higher dimensional complex space, in which it is time and again contextually collapsed and further cognitively entangled (Aerts et al. in Found Sci 4:115–132, 1999; in Lect Notes Comput Sci 7620:36–47, 2012). The observer–consumer of signs becomes the empowered ‘produmer’ (Floridi in The philosophy of information, Oxford University Press, Oxford, 2011) creating the cognitive outcome of the interaction, while loosing most of any ‘classical givenness’ of the sign (Bal and Bryson in Art Bull 73:174–208, 1991). These quantum-like descriptions are now developed here in four example aesthetic signs; the installation Mist room by Ann Veronica Janssens (2010), the installation Sections of a happy moment by David Claerbout (2010), the photograph The Falling Man by Richard Drew (New York Times, p. 7, September 12, 2001) and the documentary Huicholes. The Last Peyote Guardians by Vilchez and Stefani (2014). Our present work develops further the use of a previously developed quantum model for concept representation in natural language. In our present approach of the aesthetic sign, we extend to individual—idiosyncratic—observer contexts instead of socially shared group contexts, and as such also include multiple idiosyncratic creation of meaning and experience. This irreducible superposition emerges as the core feature of the aesthetic sign and is most critically embedded in the ‘no-interpretation’ interpretation of the documentary signal.