This is one of the five earliest paintings surviving in the Royal Collection. The others are Henry VI, Edward IV, Richard III and Elizabeth Woodville. Recent dendrochronological (tree-ring) analysis indicates that this panel was painted between 1504 and 1520. It would have been part of a set of heads of kings and queens either commissioned by Henry VII or Henry VIII.

The king is depicted against a patterned background, wearing a green brocade costume with red sleeves, trimmed with brown fur; a jewelled gold chain with a ruby pedant hangs around his neck. His positioning in profile indicates that this portrait of the king may have derived from a medal, the effigy of the king at Westminster Abbey (stolen in 1546) or his donor portrait in an altarpiece. This image, with the profile head set against a patterned background, became the standard format for later sixteenth-century versions.

The artist is unidentified but would probably have been either British or Flemish, working for the royal court. Originally the painting would have been in a gilded, engaged frame which has been dismantled at some point in the painting’s history. It is now displayed in a twentieth-century reproduction Tudor frame.