31) Sir Thomas More by Hans Holbein. If I had to make a list of the greatest technical painters throughout history, Holbein would be very near the top along with van Eyck, da Vinci, and Ingres. The problem very often with painters who can apply paint photographically however; is that the emotion, or soul of a subject is very often lost in the painstaking process. If you look at the vast majority of Holbein's work, it is undoubtedly brilliant, but soul-less as well. The Ambassadors may be his most famous work, but to me it is completely uninspiring. His Thomas More, on the other hand, is absolutely riveting. One can sense that Holbein had great respect for More. I see conviction, morality, and perhaps a bit of stubborness in his face. At the same time fallibility and a tiny hint of fear--perhaps in the knowledge of his own fate. If this canvas inspires you to learn more about More, rent A Man for All Seasons; it's a great movie. I believe this is the greatest painting Holbein ever created, although his portrait of Charles de Solier in Dresden comes pretty damn close.
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Frick Collection, New York