In the 1990s, Christopher Wool expanded his exploration into the medium of painting by incorporating silkscreen techniques into his work, marking a significant evolution in his artistic practice. This period saw Wool delving into the juxtaposition of order and chaos, employing layers of floral patterns and decorative motifs derived from industrially sourced images. His utilization of silkscreen allowed him to layer these patterns in complex arrangements, where the images would overlap, bleed, and merge, creating a dynamic field of visual noise and expressive abstraction.

Wool's process involved using readymade patterned paint rollers to apply black enamel paint onto aluminum panels, activating a dialogue between industrial decoration and fine art. This technique highlighted the tension between abstraction and figuration, as these everyday patterns assumed a new, purely abstract existence on the canvas. Critics have described Wool's compositions as springing from the spirit of the urban landscape, likening them to the unruly growth of a vacant lot, with a level of distortion that intensifies their visual impact.

By the mid-1990s, Wool transitioned from using rollers to employing silkscreens, a technique that allowed him to magnify the floral images and explore the effects of layering more systematically. This shift from reduction to accumulation enabled Wool to construct paintings that were dense with overlapping forms, enhancing their complexity and depth. The layers of thick black enamel created through this process resulted in a visual cacophony, where organic forms would emerge from an undergrowth of painterly gestures, highlighting Wool's interest in the interplay between control and chance, order and disruption.

Wool's black paintings from this era are characterized by their monumental scale and intricately layered imagery, serving as a testament to his investigation of painting's possibilities within post-modern and post-conceptual contexts. The works are seen as a critical commentary on the genre of painting itself, challenging traditional notions of authorship and creation through their emphasis on process, technique, and the visual experience of looking.

Christopher Wool's silkscreens from the 1990s represent a pivotal moment in his career, where the artist pushed the boundaries of painting to explore new territories of expression and conceptual inquiry. Through his innovative use of materials and techniques, Wool contributed significantly to the dialogue surrounding contemporary painting, reaffirming its relevance and potency in the face of evolving artistic paradigms​ (Sothebys.com)​​ (Sothebys.com)​​ (Camden Art Centre)​.