By using an old phrase about ambiguity, I look at the different ways of looking at art without getting on board with the attitudes of others, particularly the privileged with their restricted cultural background. Leonardo said that art is a cosa mentale (rather as McLuhan did later), and as a result, art does not so much act on people as that people react to art in light of their experiences. Those experiences include various cognitive habits such as reactions to trompe l’oeil, pareidolia, and other gestalt processes. The reactions of people like us and of our various ancestors at different stages have been different, and the chapter discusses those characteristics at three different stages of the evolution of the production of art—it was from this that I originally identified the seven stages of ambiguity that form the core of the chapter. I point out that some famous works of art involve breaking arbitrary rules, others pay homage to earlier works which they evoke—all belong to the last 300 years in the period that art historians recognize as one where people produced “Fine” Art which I call Art 1. In doing so, the artist appears to play with the concept of indeterminacy that underlies the concept of the expectation of meaning in the marks artists have always made. Various examples of rock art (which I call Art 2) show that reducing that indeterminacy was part of the way in which people determined a canonical message in the scenes they represented. As we survey the world of art, it becomes clear how important the role of commerce has been in the last three or four hundred years, as artists have used new possibilities that resulted from social change (such as the damage to the unique power of the Catholic Church) and technological change (invention of paper and oil paint, use of canvas, as well as printing) and sought to make a living from their labors without being tied to patronage. At the same time, gate-keepers—particularly in museums, galleries, and new Academies of Art—determined cultural rules of the emerging market. A survey of some of the early examples of art (which I have called and defined as Art 3) allows us to begin to understand some of the cognitive processes that were involved in our ancestors slowly beginning to produce meaningful marks and talk about their meanings in the context of the cultural knowledge of people in the society. The chapter ends with an Essay about the Trinil Shell, an example of Art 3, and one of the anthropomorphs from Northwest Central Queensland, an example of Art 2, and a discussion of the social role of cultural context in interpreting them as art.