What a great question, Carl! My pick would be this one by Vincent Van Gogh.
Not only because he is my favorite painter, but I like it because on the wall in the background is a set of Japanese prints that Van Gogh had put up on his wall. Japanese art or prints was something he liked and was an influence for his work.
"In a confusing universe some things just make sense." --STV (BBCA)
"Years ago my mother used to say to me, she'd say, 'In this world, Elwood, you must be' — she always called me Elwood — 'In this world, Elwood, you must be oh so smart or oh so pleasant.' Well, for years I was smart. I recommend pleasant. You may quote me." — James Stewart as Elwood P. Dowd
Not only are eyes windows to the soul, but our eyes look to the skies for home.
This is called the Chandos Portrait because the first family we know of that owned it (in 1747) was named Chandos (duh!). We also know that when it came to the Chandos collection, it already had the reputation that this was a portrait of William Shakespeare. Really, who knows who the hell it is? Nevertheless, this is one of the three portraitures of Shakespeare from which all others are derived (the other two are: the engraving in the First Folio and the statue of Shakespeare over his tomb in Stratford). I like it that the man in the painting has an earring. In the Early Modern Period this meant much the same as it still does: the wearer was a little more bohemian than others. The Chandos Portrait now resides in the National Portrait Gallery in London.