English: Christina of Denmark, Duchess of Milan. Oil on oak, 179 × 82.5 cm, National Gallery, London.

Holbein painted this portrait of Christina of Denmark, the young widowed Duchess of Milan, for Henry VIII of England, who was considering her as a possible wife. Thomas Cromwell sent Holbein to Brussels, accompanied by Philip Hoby, to draw the duchess, and she sat for him for three hours. John Hutton, the English representative in Brussels, wrote of the result that "Mr Haunce ... hathe shoid hym self to be the master of that siens [science], for it is very perffight". Henry was so delighted with Christina's portrait that, according to the imperial ambassador Eustace Chapuys, "since he saw it he has been in much better humour than he ever was, making musicians play on their instruments all day long". Holbein painted Christina's portrait in oils shortly afterwards, and the work has been recognised as one of his finest. In the event, Henry never secured the wary duchess as his wife. "If I had two heads," she said, "I would happily put one at the disposal of the King of England". (References: John Rowlands, Holbein: The Paintings of Hans Holbein the Younger. Complete Edition. Boston, David R. Godine, 1985. ISBN 0879235780, pp. 116–17; Derek Wilson, Hans Holbein: Portrait of an Unknown Man, London: Pimlico, 2006, ISBN 1844139182, p. 251.