Starting out as a "Neo-Pop" painter, Christopher Wool explores painting's elusive and allusive qualities with a variety of methods including using commercial rollers to apply decorative patterns on white panels. "I became more interested in 'how to paint it' than 'what to paint,'" he claims. Wool's paintings about painting were engaging, gaining praise and collectors early on.

In the late 1980s he was inspired by the words "SEX and LUV" spray painted on a truck outside his studio, and he embarked on a series of bold text-based works known as "Black Book" paintings. According to art critic Ken Johnson, these were "some of the punchiest paintings in 1980s and 1990s." However, they represent only one aspect of Wool's œuvre. His intelligent and edgy work earned him a 1998 retrospective organized by the Museum of Contemporary Art, Los Angeles. He was also chosen to exhibit in ILLUMInations at the 54th Venice Biennale.