Maurizio Cattelan's sculpture of a kneeling Adolf Hitler is the most controversial of an absorbing collection of 39 lots coming to Christie's.
Its Bound to Fail auction on May 8 in New York features works on the theme of failure from the leading names in modern, post-war and contemporary art.
Titled Him, Cattelan's 2001 work has a $15m high estimate.
Intended for approach from the rear, the viewer initially sees a kneeling, child-like figure in prayer.
Christie's explains: "Once the viewer circles around to the front, the reviled subject is immediately identified. In doing so, the viewer's initial impression is forcibly redefined, the realization becoming a powerful reminder that the face of evil is not always obvious."
Cattelan had conflicting emotions while creating the piece.
"I wanted to destroy it myself. I changed my mind a thousand times, every day. Hitler is pure fear; it's an image of terrible pain. It even hurts to pronounce his name.
"I'm not trying to offend anyone. I don't want to raise a new conflict or create some publicity; I would just like that image to become a territory for negotiation or a test for our psychoses."
In 2001, a Cattelan sculpture of a meteorite striking Pope John Paul II auctioned for $886,000.
The auction also features Jeff Koons' One Ball Total Equilibrium Tank - a basketball hovering in a tank of water.
This pre-dates Damien Hirst's shark, The Physical Impossibility of Death in the Mind of Someone Living, by six years. Christie's has not provided an estimate.
It is the first time either piece has been offered at auction.
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