“Painting, for me, is often a struggle between the planned and the unforeseen. The best paintings are the ones that you could not have imaged before you began […] Of course the worst paintings are created in this way as well”
—Christopher Wool

A monumental and electrifying testament to Christopher Wool’s radical reinvention of painting at the turn of the millennium, Lester’s Sister (My Brain) stands as an emblem of the artist’s signature fusion of mechanical reproduction and gestural abstraction. Executed in 2000, the work epitomises Wool’s masterful command of the silkscreen process, a technique that he has wielded to dismantle traditional hierarchies of painting and redefine the very act of mark-making. With its stark monochromatic palette, rich textural complexity, and arresting interplay of erasure and assertion, Lester’s Sister (My Brain) is an essential example of Wool’s oeuvre, a compelling link between his earlier text-based works and his later, more gestural abstractions.
 

After years of working with mechanical techniques and imagery, notably stencilled patterns and letters, Wool reintroduced gestural mark-making into his practice in 1995 with works like Maggie’s Brain, located in The Art Institute of Chicago. In 1998, the artist began appropriating his own paintings as the base images for autonomous works—taking a finished picture, using it to create a silkscreen, and then reassigning the image onto a new canvas. The original painting is metamorphosised into a crisp, flattened image, which Wool either leaves as such or builds upon with enamel paint and further screen printing. Executed in 2000, Lester’s Sister (My Brain) is a masterful product of this transition in style and technique, representing the artist’s unique approach to the painterly medium.
 

At first glance, Lester’s Sister (My Brain) presents a field of seemingly frenetic forms, layered and distorted across the linen surface. Wool divides his source painting into four screens placed with the edges slightly misaligned, dissecting the flow of the original work into disjunctive quadrants. His use of silkscreened imagery—a hallmark of his practice—injects an industrial, mechanised quality into the work, recalling the serial production techniques of Andy Warhol’s Pop practice. Going considerably further than Warhol’s serial repetitions of consumerist and cultural icons, Wool embraces imperfection and misalignment, deliberately allowing slips, drips, and overpainted layers to disrupt the regimented order of the silkscreened motifs. This disorientation is taken further as Wool draws over the screen-printed image with enamel spray paint. The result is a work in flux, its compositional structure constantly wavering between control and chaos, a fundamental tension that has defined the artist’s career.
 

Wool’s work exists within a stylistic and technical space between Pop Art and Abstract Expressionism. A crucial touchstone for his practice is the legacy of Jackson Pollock’s all-over compositions, where gesture is both spontaneous and highly orchestrated. In Lester’s Sister (My Brain), Wool channels the physical immediacy of Pollock’s drip paintings while subverting their heroic individualism with a process more akin to mechanical reproduction. As Anne Pontégnie notes, ‘The silkscreen process allows Wool to play with scale, repetition, and rhythm. At the same time, it makes all of his work available as a repertory of form. At the heart of his corpus, the question of originality has entirely disappeared.’ⁱ This dissolution of the ‘authentic mark’ places Wool’s work in dialogue not only with Pollock but also with contemporaries like Richard Prince, whose appropriations of mass-media imagery interrogate authorship and cultural memory. Wool and Prince collaborated on text-based paintings in 1988, rendering Prince’s iconic Joke Paintings—one of which is being offered concurrently in this sale—in Wool’s characteristic black stencilled letters on white canvas.

 

The raw, urban energy of Lester’s Sister (My Brain) is deeply rooted in Wool’s early influences. Growing up in Chicago in the 1960s before moving to New York in the 1970s, Wool was profoundly shaped by the visual and political landscape of the city. The aesthetics of street art, graffiti, and industrial signage infiltrate his work, giving it a distinct edge that speaks to a broader urban consciousness. As Glenn O’Brien observes, ‘Christopher Wool takes it to the bridge, spanning abstract expressionism and pop, drama and comedy, funk and the sublime. The emblem of his advanced funkiness is his spray squiggle—with all the innocence of an amateur doodle, yet all the stealth of a master brushstroke.’ⁱⁱ In Lester’s Sister (My Brain), this tension is fully realised: the silkscreened patterns provide a structured framework, but Wool’s intervention—through misaligned printing and expressive spray paint—infuses the work with raw spontaneity, challenging the viewer’s perception of painterly intent.

“With their grand scale, bold unapologetic presence and their stark, black and white confidence, Wool’s paintings seem like an indescribable urban cool, a tense fusion of intellect and emotion, control and chaos.”
—Katrina M. Brown

An exceptional example of Wool’s practice, Lester’s Sister (My Brain) is a work of striking visual dynamism and conceptual depth. The artist himself has described his method as ‘a struggle between the planned and the unforeseen,'ⁱⁱⁱ an ethos that manifests palpably in the intricate layering and spontaneous line-work at play in this piece. For collectors and institutions alike, Lester’s Sister (My Brain) represents not only a critical moment in Wool’s artistic trajectory but also a broader meditation on the language of painting in the contemporary era.

 

Collector’s Digest

 

• In 2024, Christopher Wool and curator Anne Pontégnie organised an exhibition titled ‘See Stop Run’ (14 March-28 July) which featured 72 of his works displayed in a vacant, derelict lower Manhattan office space. The exhibition was heralded by critics as hugely successful, timely and unique. Writing for the Brooklyn Rail Richard Hell claims, ‘You have to see this show or you will regret missing it. I’m not aware of anything much like it at any time recently or otherwise’.
   

• Christopher Wool’s works have been widely exhibited in prominent international institutions, including major solo shows at the Solomon R. Guggenheim Museum in New York, the Museum of Contemporary Art in Los Angeles, and the Art Institute of Chicago, cementing his place as one of the most influential painters of his generation.
   

• Wool’s work is included in numerous noteworthy international collections such as the Museum of Modern Art, New York; Musée National d’Art Moderne, Centre Georges Pompidou, Paris; and Tate Modern, London.

 

 

ⁱ Anne Pontégnie, ‘At the Limits of Painting’, in Christopher Wool, Cologne, 2012, p. 300.

ⁱⁱ Glenn O’Brien, ‘Apocalypse and Wallpaper’, in Christopher Wool, Cologne, 2012, p. 9.

ⁱⁱⁱ Christopher Wool, quoted in Christopher Wool, Cologne, 2012, p. 266.