Picasso's La Gommeuse will auction with a $60m estimate in November.
The 1901 work stems from the first year of Picasso's blue period (1901-1904), when the teenage artist was plunged into depression following the suicide of a friend.
One of few blue period works still on the private market, it will appear at Sotheby's impressionist and modern art evening sale on November 5 in New York.
"Above all others, Picasso's Blue Period is prized as his breakthrough - this is the moment Picasso becomes Picasso," explained Simon Shaw, co-head of Sotheby's worldwide impressionist and modern art department.
"With her dreamy gaze and frank sensuality, the cabaret dancer in La Gommeuse ushers in a new visual idiom for the 20 century."
This canvas offers a further treat for Picasso fans. Because on the reverse is another Picasso - a depiction of his naked flatmate, Pere Manach, urinating.
The piece is from the collection of billionaire William Koch.
He bought it for £1.4m ($1.7m) in 1984. It first sold in 1949, for $3,600.
Picasso remains the most collectible figure in the art world. His Les Femmes d'Alger Version O (1955) broke the art auction record when it sold for $179.3m in May.
Koch, 75, is also consigning a 1908 work from Monet's water lilies series. It has a $50m high estimate - a significant increase on the $8.4m Koch bought it for in 2000. A 1906 example of the 250 water lilies Monet painted recently sold for £31.7m ($54m).
View this superb Picasso-signed postcard we have for sale.
Please sign up to our free newsletter to receive exciting news about art and photography auctions.