Van Cleve's portrait of Henry VIII is of comparable size to his portrait of Francis I in the Philadelphia of Art (Francis I measures 72.1 x 59.2 cm) and the compositions and costumes in both are similar. It has been suggested that they were painted as pendants to commemorate the meeting of Francis and Henry in Calais and Boulogne (21-29 October 1532). An alternative view is that van Cleve based the Henry VIII portrait on that of Francis I (presumably already being familiar with Henry's frequently portrayed features) without having met the English king, in the speculative hope of gaining future English royal commissions.

If these two paintings are a pair we can consider them in the same manner as van Cleve's Self Portrait and Katlijne van Mispelteeren (also in the Royal Collection). The kings are set against a green background on which their distinctive hats cast shadows, with the light source in both originating from the left. The artist also included fictive shadows cast by the imagined frames in order to enhance the illusion, and a table of similar width runs in front of both kings, although the cloth in the Philadelphia portrait is red and that in the present work is green. Van Cleve is not recorded as having worked in England; he may have painted both these portraits while in France.

The inscription on the scroll in the portrait of Henry VIII translates as, 'Go ye into all the world, and preach the gospel to every creature' (Mark 16:15). The same words were inscribed on Holbein's title page for the Coverdale Bible of 1535 which has sometimes been seen as a key to dating this portrait, but it is one of ten biblical quotations on that page. It seems more likely that van Cleve's inclusion of these words - in Latin rather than English - is more Catholic than Protestant, and was intended to celebrate Henry's papal title of Defender of the Faith, which he won in 1521.

Henry VIII's clothes were designed to convey magnificence and to enhance the reputation of the Tudor court both at home and abroad. In 1516 he was described by the Venetian Ambassador as 'the best dressed sovereign in the world'. Portraits like this predominantly show the king wearing colours traditionally associated with monarchy (black, white, red and gold) in rich fabrics – silk, fur and cloth of gold, with an abundance of large jewels. During the early part of Henry's reign male doublets were cut fairly low across the chest. Here his linen shirt worn beneath has been pulled through slashes in the cloth of gold fabric of the doublet to form elliptical puffs of fabric. Catalogue entry partly adapted from The Northern Renaissance. Dürer to Holbein, London 2011