Andy Warhol, "Shot Sage Blue Marilyn" (1964), acrylic and silkscreen ink on linen, 40 x 40 inches (image courtesy Christie's)

An iconic 1964 silkscreen portrait of Marilyn Monroe by Andy Warhol, estimated at $200 million — which, if achieved, would make the painting the most expensive 20th-century painting to be sold at auction — is headed to Christie’s in May.

Titled “Shot Sage Blue Marilyn,” the painting belongs to a series commonly known as the Shot Marilyns, comprised of four individual portraits of the star whose name became synonymous with the manic hypersexualization of famous women in 1950s and ’60s Hollywood culture. Each square canvas in the series measures 40 by 40 inches, with identical facial outlines and backgrounds painted variously red, orange, light blue, and sage blue. After the actress died from a drug overdose that was ceaselessly sensationalized in the media, Monroe became one of Warhol’s favorite subjects throughout the 1960s, with all of his paintings of her using the same Niagara (1953) publicity photo. Examples hang in some of the most prestigious institutions in the world, including the Tate in London and the Cleveland Museum of Art

The Shot Marilyns got their name when performance artist and friend-of-a-friend Dorothy Podber visited Warhol at his New York studio, which he called the Factory. Noticing a stack of freshly-painted works, Podber asked Warhol if she could shoot them. Warhol, assuming that she was asking for permission to photograph them, said yes, before Podber drew out a revolver and shot a bullet through the foreheads of the Marilyns. A few years later, Valerie Solanas would shoot and nearly kill Warhol at the Factory, imbuing the paintings’ scars with additional significance.

Christie’s will be auctioning the work in a philanthropic sale to benefit the new Thomas and Doris Ammann Foundation Zürich, which a press release describes as “dedicated to improving the lives of children the world over by establishing support systems centered on providing healthcare and educational programs.” The Ammanns were siblings and ran a gallery in Zürich beginning in the late 1970s, dealing in works spanning the Impressionist period to contemporary art. Doris headed the gallery until last year, when she died at the age of 76.

Hyperallergic has contacted Christie’s and Thomas Ammann Fine Art to request additional details on the Thomas and Doris Ammann Foundation. Fortune reports that the foundation has committed to funding children’s health and education causes for the next three to six years and will be funded in part by the sale of the portrait.

Georg Frei, chairman of the board of the foundation and partner of the late Doris Ammann, said in a statement that the painting “isolates the person and the star: Marilyn the woman is gone; the terrible circumstances of her life and death are forgotten.” He compared Monroe’s smile to that of the Mona Lisa, echoing a parallel drawn by Alex Rotter, Christie’s chairman of 20th- and 21st-century art. Calling the work “the absolute pinnacle of American Pop and the promise of the American Dream,” Rotter indicated that it stands beside Botticelli’s “Birth of Venus,” Da Vinci’s “Mona Lisa,” and Picasso’s “Les Demoiselles d’Avignon” as one of the “greatest paintings of all time.”

The sale in May will also test the current valuation of Warhol’s masterpieces. Last fall, Sotheby’s sold “Nine Marilyns,” a nearly seven-foot-tall, black-and-white silkscreen from 1962, for $47.4 million. Sotheby’s also sold Warhol’s most expensive work to date, “Silver Car Crash (Double Disaster)” (1963), which fetched $105.4 million in 2013. According to Bloomberg, works by Warhol have sold privately for over $100 million.

“Shot Sage Blue Marilyn” is distinguished by the method Warhol used to produce it — a more detailed and demanding technique that he developed in 1964 and used very sparingly because it was so involved. He abandoned that process after creating a small number of the Marilyn portraits, according to Christie’s press release.

The most recent sale of a work from the Shot Marilyn series occurred in 2007, when hedge fund manager and New York Mets owner Steven Cohen purchased the turquoise one in 2007 for $80 million. The two other canvases in the group belong to publisher Peter Brant — who purchased the light blue canvas for a mere $5,000 in 1967 — and shipping heir Philip Niarchos — who bought the red one for $3.6 million in 1994.

Avatar photo

Jasmine Liu

Jasmine Liu is a former staff writer for Hyperallergic. Originally from the San Francisco Bay Area, she studied anthropology and mathematics at Stanford University.