The Smithsonian offers a great one-hour "introductory" tour where they tell you all the background of about 10 paintings. Here are my favorite:

Ginevra de' Benci, c.1474/1478

Leonardo da Vinci

Likely an engagement portrait (to a wealthy man at least twice her age), this features a juniper tree. The Italian word for juniper is "ginepro", which is perhaps a pun on her first name. It is also a Italian Renaissance symbol for chastity. According to Wikipedia, the museum paid $5 million for it in 1967. It's oil on wood, and the only da Vinci in the Western Hemisphere.

This is the back of the portrait's wooden panel. VIRTUTEM FORMA DECORAT means Beauty adorns virtue. It sounds to me like this painting was sent to her future husband to assure him she would indeed be a great trophy wife...

Further evidence that money doesn't by happiness. This is Lorenzo de' Medici, who escaped assassination in 1478. Wax portrait statutes of him were placed in churches throughout Florence to celebrate his survival and may have been used as models for this terracotta bust. But he certainly doesn't LOOK to thrilled to be alive, does he?

The Alba Madonna, c. 1510 by Raphael
Painted in the Medicis' favorite circular format, this painting shows Mary looking on as John the Baptist (center) hands baby Jesus a cross, symbolizing Jesus' acceptance of his ultimate sacrifice. The tour guide emphasized how both the scenery and the background are very natural (in contrast to earlier work that I didn't like enough to attempt to photograph).

Lucretia, by Rembrandt van Rijn, oil on Canvas, 1664
Apparently this captures the moment just before Lucretia kills herself to restore her and her family's honor following her rape. She's selected some of her finest clothing for the moment.
Here's the tale, as told by davidrumsy.com: According to the Roman historian Livy, Lucretia, the wife of a Roman nobleman, was known for her virtue and loyalty. Sextus Tarquinius, the son of the ruling tyrant, raped her while her husband was away. The next day Lucretia told her husband and father what had happened and, in their presence, took her own life, choosing death over dishonor.

Madam Monet with her son, Claude Monet

Self portrait, 1889, Vincent van Gogh

Painted after he voluntarily entered an asylum and suffered a breakdown there.

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