Which Picasso painting was the first to sell for over $100 million at auction?

The first Picasso painting to sell for over $100 million at auction was Garçon à la pipe, or Boy with a Pipe.

Picasso painted the work in 1905, when he was 24, shortly after settling in Montmartre, Paris. It belongs to his Rose Period and shows a Parisian adolescent wearing a flower garland and holding a pipe. The boy was reportedly a local named P’tit Louis.

On 5 May 2004, Sotheby's sold the painting in New York for $104.168 million. The widely reported total included the buyer's premium: the hammer price was about $93 million, with roughly $11 million in auction-house commission. Its presale estimate had been $70 million.

The sale briefly made it the most expensive painting ever sold at auction, although critics disagreed about whether the work deserved “masterpiece” status. It is often confused with later Picasso auction stars such as Les Femmes d'Alger (Version O).