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1. Nov 5th 1948 by Jackson Pollock

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Jackson Pollock’s 1948 painting entitled Nov 5th 1948 was arguably his greatest masterwork, the most vivid expression of the painter’s unique style. When it was sold by David Geffen in 2006, it became the world’s most expensive painting in history at a price-adjusted $149.70 million dollars.

2. Woman III by Willem de Kooning

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This, the second most-expensive painting in the world was among the collection sold by David Geffen in 2006. Woman III by Willem de Kooning was among six painted by the artist between 1951 and 1953, with this version ending up at the Tehran Museum of Contemporary Art– where it would be later hid from the public due to its inadherence to the government’s rules of morality.

3. Portrait of Adele Bloch-Bauer by Gustav Klimt

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Once the world’s most expensive painting, Gustav Klimt’s Portrait of Adele Bloch-Bauer took three years to create in oil and gold. The painting was commissioned by a Swiss sugar magnate, a fan of Klimt and the husband of the painting’s subject.

4. Portrait of Dr. Gachet by Vincent Van Gogh

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This painting was sold to Ryoei Saito in 1990. This would become Van Gogh’s most expensive painting to date, selling for an impressive $82.5 million ($136.1 million today)

5. Bal au moulin de la Galette, Montmartre by Pierre-Auguste Renoir

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Renoir’s sole entry in the top 15 most expensive paintings is his work Bal au moulin de la Galette. This painting was sold in 1990 to Ryoei Saito, the chairman of a Japanese paper company and a collector of fine art.

6. Garçon à la pipe by Pablo Picasso

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The “boy at the pipe� is Picasso’s most highly priced painting on this list, having sold for $104.2 million in 2004 (currency adjusted to $118.9 million). The boy in the painting was among the community of entertainers living in the Montmartre section of Paris, many of which were the subjects of Picasso’s red period.

7. Irises by Vincent Van Gogh

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Van Gogh’s second landscape on this list is named simply Irises, showing at first glance a rather sunny world that was much in contrast to the artist’s disposition.

8. Dora Maar au Chat by Pablo Picasso

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One of Picasso’s greatest works was a portrait of his then-mistress Dora Maar. Miss Maar was 29-years-old at the time, 26 years younger than Picasso. The subject was seated with a black cat perched on her shoulder.

9. Portrait de l’artiste sans barbe by Vincent Van Gogh

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Van Gogh’s beardless self-portrait shows the artist hiding something– namely a nasty, Absinthe-fueled shaving accident. In the year of this portrait, Van Gogh cut off part of his ear amidst a bout of severe depression that would later lead to his suicide.

10. Massacre of the Innocents by Peter Paul Rubens

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Peter Paul Rubens’ Massacre of the Innocents is both the earliest work on this list as well as its only religious-inspired painting. Painted in 1611, Massacre represents a scene from the Bible’s Gospel According to Matthew.

11. Triptych by Francis Bacon

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As one of the premier artists of the surrealist period, Irish painter Francis Bacon explored the tri-panel format of painting called the Triptych. His work of the same name is the most recent sale on this list, going for $86.3 million.

12. Les Noces de Pierrette by Pablo Picasso

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Picasso’s Les Noces de Pierrette is among the artist’s blue period, including some of his most famous works. At the time, Picasso was facing poverty and the loss of a close friend who had recently committed suicide. It was works like this that would prove cathartic for the artist- and lead him to wealth later in life.

13. False Start by Jasper Johns

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The lone contemporary piece in the top 15 was among a large collection of art sold by media mogul David Geffen in 2006.

14. A Wheatfield with Cypresses by Vincent Van Gogh

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One of two Van Gogh landscapes in the top 15 is A Wheatfield by Cypresses, an idyllic nature scene with the artist’s signature swirling skies. Wheatfield was owned by philanthropist/ diplomat Walter Annenberg until his death in 2002, and is now a part of his estate.

15. Yo, Picasso by Pablo Picasso

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Picasso’s 1901 self-portrait may not be his most instantly recognizable, but it certainly did capture a hefty price on the fine art market. Long before Picasso began experimenting with cubism and surrealism, his early oil works were equally as stunning. An interesting anecdote about Picasso, his full name is “Pablo Diego José Francisco de Paula Juan Nepomuceno María de los Remedios Cipriano de la Santísima Trinidad Martyr Patricio Clito Ruíz y Picasso�.