Between 1988 and 2000 Christopher Wool created approximately seventy-five large-scale word paintings and very few works on paper. The words themselves, appropriated from popular culture such as movies, music and books, were placed within the context of painting; their meanings obscured and their function more closely aligned with imagery than with vocabulary.

Wool started the word paintings using store-bought stencils but soon began to explore fonts and create his own stencils in custom sizes. Focused on the process, the large proportionately-scaled stencils were meticulously placed on the panel so that everything would be just right. The resulting defects and flaws that were inherent to the process of creation became integral parts of each finished work.

In 1989 Wool created a series of paintings featuring mostly nine-letter words describing character types. Evenly spaced, with three letters on three lines, the series includes words such a celebrity, hypnotist and anarchist along with the word prankster. The meanings of these words, within the context of Wool’s artwork, are ambiguous. (Is Wool referring to the painting? to the viewer? or to himself, the artist?) Despite the uncertainty of the significance of the text, the selection of this particular word drawing as a gift for his friend and studio assistant was very likely deliberate.