Andy Warhol’s enduring legacy lies in his ability to turn the icons, obsessions, and tragedies of modern life into timeless works of art.

Across his most celebrated series, from the glittering allure of Marilyn Monroe to the haunting imagery of the Death and Disaster paintings, Warhol blurred the boundaries between celebrity and mortality, glamour and decay.

His silkscreen technique, borrowed from commercial printing, became a vehicle for both repetition and reflection, transforming familiar images into profound cultural commentary. The following five works represent the best-selling examples of his oeuvre at auction.

Andy Warhol’s Shot Sage Blue Marilyn (1964) stands as one of the most celebrated and valuable works in modern art history, having sold at Christie’s New York for a record-breaking £158 million ($195 million) in 2022. The 40-inch acrylic and silkscreen on linen epitomises Warhol’s fascination with fame, beauty, and mass reproduction. Warhol's Shot Marilyns were so named after performance artist Dorothy Podber fired a gun through several canvases. Beyond its artistic significance, the sale marked a milestone for philanthropy, with proceeds benefiting the Thomas and Doris Ammann Foundation in support of global healthcare and education initiatives. Often compared to masterpieces like The Mona Lisa and The Birth of Venus, Shot Sage Blue Marilyn is now firmly cemented in the cultural canon as an icon of the 20th century.

Andy Warhol’s Silver Car Crash (Double Disaster) (1963) is one of the most powerful and haunting works from his Death and Disaster series, confronting the viewer with the stark reality of tragedy through the lens of mass media. Spanning over eight feet across two canvases, the diptych juxtaposes a violent car crash scene with an expanse of reflective silver paint, evoking both detachment and fascination. Using his signature silkscreen technique, Warhol transforms an image of devastation into an unsettling commentary on celebrity, mortality, and society’s obsession with sensational imagery. When it sold at Sotheby’s in 2013 for £65.7 million ($105.4 million), the piece not only set a record for Warhol at the time but also reaffirmed his enduring ability to capture the contradictions of modern life, beauty in horror, glamour in catastrophe.

Andy Warhol’s White Disaster [White Car Crash 19 Times] (1963) is a monumental work from his Death and Disaster series, confronting themes of mortality and media repetition with chilling precision. Measuring over twelve feet tall, the painting features the same harrowing car crash image silkscreened nineteen times in stark black and white across a ghostly white canvas. This relentless repetition, paired with the absence of colour, amplifies the sense of numbness and detachment created by constant exposure to tragedy in the media. In 2022, the work sold at Sotheby’s for £72 million ($85.4 million), underscoring both its rarity and emotional intensity. White Disaster exemplifies Warhol’s ability to transform scenes of violence into profound meditations on fame, death, and the desensitising power of mass communication.

Andy Warhol’s Triple Elvis [Ferus Type] (1963) captures the essence of celebrity culture and repetition that defined his Pop Art vision. Featuring three overlapping images of Elvis Presley dressed as a cowboy, the work was created using silkscreen ink on silver paint, evoking both the glamour and impermanence of stardom. First exhibited at the Ferus Gallery in Los Angeles in 1963, it reflects Warhol’s fascination with fame as a modern form of iconography, part myth, part mass-produced product. The shimmering metallic surface and rhythmic duplication give the impression of motion, as if Elvis is caught mid-performance, endlessly projected like a film reel. When it sold for £52 million ($81.9 million) at Christie’s in 2014, Triple Elvis [Ferus Type] reaffirmed Warhol’s status as the ultimate chronicler of celebrity and the American dream.

Andy Warhol’s Green Car Crash (Green Burning Car I) (1963) stands as one of the most striking and visceral works from his Death and Disaster series, exploring society’s morbid fascination with violence and tragedy. The painting depicts a harrowing car accident sourced from a press photograph, silkscreened repeatedly over a vivid green background that heightens its unsettling impact. By pairing a shocking image of destruction with a lush, almost seductive hue, Warhol exposes the tension between horror and beauty, detachment and empathy. Created during a period when he was examining the darker side of American media culture, the work serves as both a critique of mass consumption and a meditation on mortality. When it sold at Christie’s in 2007 for £36 million ($71.7 million), Green Car Crash cemented its place as one of Warhol’s most emotionally charged and rare masterpieces.