Christopher Wool's artistic journey in the 2000s is marked by significant evolution and experimentation, reflecting his deep engagement with the process of creation and the boundaries of abstraction. During this period, Wool's exploration of various mediums, collaborative efforts, and thematic focus on urban life and abstraction signified a pivotal phase in his career, characterized by both continuity and innovation. The beginning of the 2000s saw Wool further engaging with the urban landscape through his photography, as exemplified in his "East Broadway Breakdown" (2004) project. This series, which began in the mid-1990s and was completed in 2002, featured a collection of black and white photographs taken at night in New York City. Capturing scenes of desolation and the overlooked aspects of urban life, these photographs oscillate between abstraction and representation, echoing the gritty aesthetic and emotional resonance of street photography. Wool's work in this vein is noted for its portrayal of estrangement and solitude, with a deliberate focus on the "least attractive things imaginable," thereby challenging established notions of beauty​ (The Art Story)​. In his painting practice during the early 2000s, Wool underwent a significant shift with the development of his 'gray works.' These works were characterized by a complex layering process that involved photographing, silkscreening, and reworking his own previous works. This method led to the creation of paintings that were deeply involved with the process of art-making, demonstrating a dynamic interplay between erasure and creation. By employing techniques such as spraying enamel and using towels soaked in turpentine to remove parts of the paint, Wool engaged in a continuous cycle of adding and subtracting, which resulted in compositions that are rich in gestures and interruptions. This approach has been likened to the gestural techniques of Abstract Expressionists, though Wool's method also incorporates digital manipulation and a critical reflection on the act of painting itself​ (The Art Story)​. Collaboration became another avenue for Wool's artistic exploration, notably in his work with artist Josh Smith. Together, they developed a body of work that emphasized the digital manipulation of images, bypassing traditional painting processes in favor of a 'silent' dialogue between artists. This collaboration, which involved reworking digital images of each other's work, highlighted the role of technology in contemporary art production and challenged conventional notions of artistic authorship and the physical act of painting​ (The Art Story)​. Throughout the 2000s, Wool's work continued to gain recognition and was featured in significant exhibitions, including a retrospective at the Guggenheim Museum in New York City, which later traveled to the Art Institute of Chicago​ (Wikipedia)​. His influence was also felt in the art market, where his works, particularly the word paintings from the late 1980s to early 2000s, commanded high auction prices, underscoring his critical and commercial success​ (Wikipedia)​. Christopher Wool's artistic endeavors in the 2000s are emblematic of his willingness to push boundaries and explore new territories in painting, photography, and digital art. By continuously questioning and experimenting with the processes and materials of art-making, Wool has cemented his position as a key figure in contemporary art, whose work resonates with the complexities and contradictions of the modern experience.