He was not satisfied with portraits for long. The Steelyard, of which we shall soon speak at length, gave him subject pictures to paint. King Henry took him into his service with a retainer of £30 a year, no inconsiderable sum in those days, and payment for all works done, and he soon became a painter of the pictures that are produced to commemorate state occasions. Happily he painted them better than some more modern men have been able to. It is hardly a reproach to a man that he cannot invest with special interest a picture that is to all intent and purpose composed for him, a canvas on which the figures must be handled less with regard to composition than precedence, and really Holbein did very well. His education was certain to tell in his favour; he began to enjoy the fruits of his association with the Humanists. Great painters employed at European Courts enjoyed a certain ambassadorial rank: the interest taken in art was so considerable, that the gift of a picture by a great artist was as fine a present as could be given or received, and when artists were sent to foreign courts they were often entrusted with missions not associated directly or indirectly with their profession.
To be sure, Holbein did not hold the same high position that fell to Peter Paul Rubens, but he was entrusted on two occasions with missions of a very delicate character, being instructed to paint the portraits of ladies whom the king had married or was prepared to marry. The Dowager Duchess of Milan was one of the few who declined to become Queen of England, and Anne of Cleves was one who was less discriminating. There can be no doubt that Holbein's capacity for expressing strength in the most delicate fashion imaginable appealed very strongly to his sitters. The rugged character of one man's head, the delicate lines of a woman's face, could be expressed without violence in the one case or excess of sentiment in the other, and he does not seem to have done more than present his sitters in their most attractive aspect, and with due regard to their salient characteristics. He did not flatter and he did not shock, but would seem to have found something at once pleasant and true to express about all his sitters.