Despite their seemingly informative nature, the actions depicted in the three paintings are nonsensical and and appear to have no deeper meaning; however, each painting refers to a different approach of popular painting over time. The first panel is a reference to the Renaissance aesthetic of creating paintings that appeared as if one was looking through a window. The woman washing her window is a metaphor for a Renaissance artist attempting to produce the most realistic window to another world as possible. Another proposed metaphor is how Impressionism 'cleansed' traditional painting. The second panel refers to the formalist idea of "art for art's sake" or the emphasis on compositional elements as opposed to iconography in art. The stubborn man can be seen as a metaphor for the stubbornness of modernist artists, much like the abstract expressionists, in their refusal to accept other ideals. The third panel is an allusion to the self-evaluation of postmodernist artists, like Tansey, as they contemplate their place in art history. An alternate theory is that this panel symbolizes Conceptualism and performance art which take place "in front of the surface" or are reflected by it.
Following postmodernist aesthetics, each panel is painted in Tansey's signature monochromatic style, giving the image a flattened feeling; challenging the more formal method of creating illusory depth. Tansey's style also gives the paintings a dated feeling as if they were produced in the 50's - drawing on the postmodernist idea of challenging society's preconceived notions of how things appear. In painting A Short History of Modernist Painting in a seemingly dated realsim style, Tansey speaks conceptually as to how postmodernism deconstructs the past in order to move forward. Tansey also calls attention to how representational images are inherently problematic - the contradiction between the actions represented in the paintings and their meanings - as they can be misinterpreted because they are unable to tell the entire story. Tansey discusses his approach by explaining “Pictures should be able to function across the fullest range of content. The conceptual should be able to mingle with the formal and subject matter should enjoy intimate relations with both.”