Self-portrait, given to Daniel Webster
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Ye ol titty pic
Now I too want to spend ten hours and three salaries making a big protrait of my milkers
[elbows Daniel Webster] I think she likes you!
The Wikipedia page on the painting has this gem:
Goodridge gave the portrait to statesman Daniel Webster, who was a frequent subject and possibly a lover, following the death of his wife; she may have intended to provoke him into marrying her.