Roy Lichtenstein's Nurse (1964) could set a new record for his work when it auctions at Christie's on November 9.
The lot could exceed $100m - a sum substantially above the $56m paid for the US pop artist's Woman in a Flowered Hat in 2013.
The painting is one of the most important works by Lichtenstein to come to auction in several years.
Over the course of its lifetime it has been held in both the Stroher and Kraushar collections, which were among the world's foremost repositories of pop art.
It last sold for just $1.7m in 1995, evidence of how the contemporary art market has increased in value in recent years.
Christie's comments: "Painted at the height of his career, Roy Lichtenstein's Nurse is a dazzling masterpiece ��� a celebration of the bold new imagery that changed the direction of art.
"The subject of this painting, alongside Warhol's Marilyn Monroe, Elizabeth Taylor and Jacqueline Kennedy, is one of a distinguished group of icons who take their place in the history of figurative painting�Ǫ
"Its visual supremacy and technical superiority is matched by an equally distinguished provenance. It has been owned by some of the most important and influential collectors in the history of Pop."
Lichtenstein's distinctive comic book style made him a household name. Most of his best known work is housed in the world's most prestigious art museums.
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