Christopher Wool's "Gray Paintings" represent a significant evolution in his artistic practice, characterized by a dialogue between creation and erasure. Emerging in the early 2000s, these works mark a departure from his earlier pattern and text-based pieces, embracing a more abstract and gestural approach.

The genesis of the "Gray Paintings" can be traced to a serendipitous moment in 2000 when Wool, frustrated with a painting, wiped it with a turpentine-soaked rag. The resulting blurred effect captivated him, leading to a new technique that involved applying black enamel with a spray gun and then erasing portions of it with a rag. This process created a dynamic interplay of lines and smears, producing what Wool described as "lyrical theses on the relationship between addition and subtraction" (Christie's) (Christie's).

These paintings are characterized by their ethereal quality, with layers of paint creating a palimpsest of marks and erasures. The process involves a meticulous system of layering and removal, resulting in compositions that appear spontaneous yet are carefully controlled. Wool's use of turpentine to blur and erase parts of the image introduces a sense of indeterminacy and flux, challenging the notion of a completed artwork (Christie's) (AJ – New).

Wool's "Gray Paintings" also reflect his engagement with the history of abstract painting and his response to the critical discourse surrounding the medium. Influenced by artists like Robert Rauschenberg, who famously erased a drawing by de Kooning, Wool's works explore themes of doubt, indecisiveness, and the transient nature of art. This approach aligns with the postmodern skepticism towards the idea of a definitive masterpiece, embracing instead a continual process of revision and transformation (Christie's) (Sothebys.com).

The "Gray Paintings" have been lauded for their visual complexity and the way they encapsulate Wool's unique method of combining mechanical processes with manual interventions. They stand as a testament to his ability to innovate within the medium of painting, blending elements of abstraction, graffiti, and conceptual art to create works that are both visually striking and intellectually provocative (AJ – New) (Christie's) .