Norman Rockwell's Cheerleaders (Losing the Game) will headline a sale of American art at Sotheby's.
It's valued at $2.5m-3.5m ahead of the November 18 auction.
Norman Rockwell's Cheerleaders displays the influence of the old masters
The work appeared on the cover of the Saturday Evening Post on February 16, 1952 and is one of five he painted for the publication that year.
Sotheby's finds similarities between this painting and the work of the old masters, whom Rockwell studied slavishly.
"The parallel lines created by the wood panels of the gymnasium floor recede from the foreground to converge at a single point in the distance behind the head of the center figure," says the auction house.
"This nod to linear perspective���a revolutionary invention of the early 15th century-creates a sense of depth within the two dimensional picture plane."
Rockwell's work has seen an unprecedented surge in value in recent years, with almost every piece selling for significantly higher than estimate.
His record at auction stands at $46m, set for his iconic Saying Grace in 2013.
Andrew Wyeth's Flood Plain, a painting once owned by actor Charlton Heston, is expected to realise $2m-3m.
Heston explained why Wyeth's work fascinates him: "Andrew Wyeth seems to me a most mysterious artist, searching for the inside of everything he paints.
"His subjects are people and places, usually considered separately. They are all, somehow...fraught. I can think of no other word."
Thomas Hart Benton's TP and Jake will also feature, as part of the sale of Simpsons co-creator Sam Simon's personal collection.
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