Martin Kippenberger's Jacqueline: The Paintings Pablo Couldn’t Paint Anymore is a compelling series completed in 1996, a year before the German artist's death at 44. This series comprises eight paintings and one large sculpture, Modell Winnetou, as a poignant homage to Pablo Picasso and his widow, Jacqueline Picasso. The paintings, based on photographs taken in Picasso's studio after his death, depict Jacqueline during a period of deep mourning, surrounded by the couple's belongings and Picasso's artworks. Kippenberger's approach to these portraits is notably abstract, blending sketchy renderings of Jacqueline with intense color backgrounds, stripes, and elements that reference modernist abstract painting​ (Metro Pictures)​.

The series not only reflects Kippenberger's admiration for Picasso's life and work but also delves into broader themes such as the artist's persona, the conventions of painting, immortality, and the artwork's societal role. Kippenberger, known for his expressive and sometimes controversial works, often included himself in his art, notably in self-portraits that playfully critiqued the artist's role in culture and society. In Jacqueline: The Paintings Pablo Couldn’t Paint Anymore, he explored the boundaries between portrait and self-portrait, male and female, identity, and loss, stating that by working from the last photographs of Jacqueline Picasso, he aimed to "complete" Picasso's work, turning black and white images into color paintings as a form of homage and continuation of Picasso's legacy​ (Museo Picasso Málaga)​.

The Modell Winnetou sculpture, part of the series, features six chairs of different colors surrounding a pile of wooden sticks, embodying Kippenberger's frequent use of chairs as symbols for social interaction and reflecting his time in Spain through the design reminiscent of typical Spanish café chairs​ (Metro Pictures)​.

Kippenberger's engagement with Picasso's work was a long-standing element of his career, evident in his diverse artistic expressions that ranged from painting and sculpture to performance and installation. His life in Germany, interspersed with periods in Los Angeles, Madrid, and Carmona (Spain), was marked by a prolific output and a keen awareness of art history, including a deep affinity for Picasso's work that began in childhood and continued throughout his career​ (Museo Picasso Málaga)​.

This series stands as a testament to Kippenberger's complex relationship with Picasso, blending reverence and critique, while also highlighting his own introspections on art and identity.