Cy Twombly's Winter Pictures series from 2004 exemplifies the artist's late career fascination with color, history, and nature, continuing his exploration of abstract gestures intertwined with classical and mythological themes. Created during the final decade of Twombly's life, these works underscore a period of vibrant creativity and bold use of color that marked a significant phase in his artistic journey. The series, alongside other creations from this period, showcases Twombly's unique ability to blend gestural painting with historical references, embodying the lush, saturated hues that became characteristic of his work in the 2000s.

The Winter Pictures are part of a broader exploration of themes that fascinated Twombly throughout his career, including the intersection of the past and present, the natural world, and the fluid boundaries between painting, drawing, and writing. His work from this era, including the Winter Pictures, often features large-scale formats filled with broad, sweeping gestures that evoke the vitality of nature and the richness of historical and mythological narratives. Twombly's art from his later years is noted for its dynamic energy and the use of color to convey emotional depth and complexity, bringing a fresh surge of creativity and innovation to his oeuvre.

Twombly's shift towards these themes and techniques followed his 1994 retrospective at the Museum of Modern Art in New York and was influenced by the critical success of Lepanto, a suite of twelve paintings first shown at the 49th Biennale di Venezia in 2001. This period in Twombly's work is characterized by a new approach to color and form, where slender lines and loops of paint balance expressive dynamism with elegance. The dense strokes in these pieces not only suggest the movement and vitality found in nature, such as the petals of peonies and chrysanthemums, but also reflect Twombly's ongoing meditation on poetry, history, and mythology. His works from this time are described as both vital and elegiac, capturing the spirit of Bacchanalia as well as the tranquility and reflective qualities of nature's more subdued moments​ (Gagosian)​​ (Artland Magazine)​.

Twombly's artistic legacy is marked by his innovative approach to abstraction, which seamlessly incorporated elements of calligraphy and graffiti, along with his deep engagement with the classical past. His gestural vocabulary, developed over decades, imbued every line and color with meaning, blending the poetic and the rational in a way that challenges and enriches the viewer's perception. In the Winter Pictures series, as in much of his later work, Twombly continued to explore the themes that had long captivated him, demonstrating a remarkable ability to renew and invigorate his artistic language right up until the end of his life​ (Artland Magazine)​.