How Much is Your Self Portrait Worth?

This 1981 self-portrait taken by celebrated photographer Cindy Sherman was sold at a Christie's auction last week. The final price…a record $3,890,500. The buyer was New York dealer Philippe Segalot, a former head of contemporary art for Christie's and now a private adviser to some of the world's richest art collectors.

So what's so special about a photo of a girl on a tile floor? And what drives that unimaginable price? David Ross, former director of the Whitney and San Francisco Museum of Modern Art, says that mainly, it's a function of two people wanting the same thing: "What matters to most of those collectors is winning. When art becomes a competitive sport," Ross says, "all it takes to win is the guts and the money to go further than anyone else, and then, voila, you win. And winning feels really good."

"We're living in a world of funny money," says Ross. "And money is not really a measure of anything anymore because ... it's thrown around in such unpredictable ways."

Ross, a friend of Sherman's, remembers when she was selling photos for $500 a pop. He says he's really happy for her, but that in the world of art auctions, generalizations are dangerous. That record could be broken again next week.