Back in 1964, Pablo Picasso never could have known that Nu au Plateau de Sculpteur (Nude, Green Leaves and Bust), a painting he created in just one day that year, would end up being the most expensive work of art ever sold at auction to date. In May of 2010, Christie’s auctioneer Christopher Burge coaxed bidders to new heights and unloaded the piece for a cool $106.4 million.

Picasso’s dashed-off composition may be the priciest yet, but it’s far from the only one for which a collector has forked over an astronomical sum at auction in the past two decades. Below, the seven works closest on the heels of the new record-setter.

1. Alberto Giacometti, Walking Man I

Giacometti originally cast this bronze sculpture of a six-foot-tall man midstride in 1960, as part of a commission (which he later abandoned) from Chase Manhattan Bank to create a few such figures for the bank’s Pine Street plaza in New York City. In February 2010, just four months before Nude, Green Leaves and Bust nosed it out, Walking Man I sold for $104.3 million in a Sotheby’s London showroom. Ten bidders competed for the piece; the anonymous winner placed the final bid by telephone.

2. Pablo Picasso, Garçon à la Pipe (Boy with a Pipe)

Photo source: Wikipedia

Picasso was only twenty-four years old when he painted this seated portrait of a Parisian boy holding a pipe and wearing a crown of flowers. The work, part of the artist’s Rose Period collection, was first bought by John Hay Whitney, a U.S. ambassador to the UK, in 1950, for $30,000; then, in May 2004, it fetched $104.2 million from an unnamed collector at a Sotheby’s auction in New York City. Following the transaction, some art critics expressed skepticism about Garçon à la Pipe’s high price, which they believed was largely the result of Picasso’s overall prestige, rather than the painting’s technical and creative merit. Speaking to the Washington