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Pablo Picasso. Several paintings by Picasso rank among the most expensive paintings in the world. Garçon à la pipe sold for US $104 million at Sotheby's on 4 May 2004, establishing a new price record. Dora Maar au Chat sold for US $95.2 million at Sotheby’s on 3 May 2006. On 4 May 2010, Nude, Green Leaves and Bust was sold at Christie's for $106.5 million.