The Double Head portraits are a significant part of Condo's series exhibited in shows like "Double Heads / Black Paintings / Abstractions" at Skarstedt Gallery in 2014. In these paintings, Condo employs a technique that combines elements of Cubism and Abstract Expressionism, creating fragmented and overlapping facial features that convey multiple emotional states simultaneously. This method allows Condo to explore the inner workings of his subjects' minds, presenting a visual representation of the chaotic and often contradictory nature of human thought and emotion (Sprueth Magers) (Skarstedt).

One notable example is "Double Heads on Red" (2014), which features two heads side by side, each rendered with different expressions and angles. The use of bold colors and dynamic brushstrokes adds to the intensity and complexity of the composition, highlighting Condo's skill in blending abstraction with figuration. This piece, like many others in the series, reflects Condo's interest in the psychological aspects of his subjects, moving beyond mere physical representation to delve into the deeper layers of identity (Sprueth Magers) (Skarstedt).

Condo's Double Head portraits are also characterized by their references to art history. He draws inspiration from a wide range of sources, including the works of Old Masters and modernist painters like Picasso and de Kooning. By incorporating these influences, Condo creates a dialogue between past and present, infusing his contemporary subjects with a sense of historical continuity and depth (Christie's) (Skarstedt).