Flattery as Diplomacy

Royal portrait painters walked a tightrope between accuracy and idealization. Paint the king too handsomely and he'd know you were lying. Paint him too honestly and you might lose your head. Diego Velázquez managed this brilliantly — his portraits of Philip IV are psychologically honest but never unflattering.

Marriage portraits were especially fraught. When Henry VIII needed a fourth wife, Holbein was sent to paint Anne of Cleves, and the portrait helped persuade Henry to marry her sight unseen. The story goes that when she arrived and didn't match his expectations, he was furious — historians still debate just how flattering the painting really was.