This large-scale work was commissioned to commemorate the grant of a royal charter to the Company of Barbers and the Guild of Surgeons on their merger in 1540. Presumably at the request of his clients, Holbein based the design on that of the miniatures painted on Tudor charters of privileges. Henry did not sit for this last of Holbein's portraits of him. Working from an existing sketch, Holbein painted him not so much as a living person but as an icon.^[1] The members of the company, however, were painted as individuals.

On the King’s right side are his two physicians, Dr. John Chambers and Sir William Butts and his apothecary Thomas Alsop.
The figures of Sir William Butts and the doctor John Chambers are closely related to portraits of them by Holbein (left).

On the King’s left side are his Serjeant-Surgeon, Thomas Vicary (Master 1530, 1541, 1546, 1548, 1557), his surgeons, Sir John Ayliffe (Master 1538), James Monforde (Warden 1540, 1543) and Richard Ferris (Master 1551, 1562) and his barbers, Nicholas Simpson (Master 1537), Edmund Harman (Master 1540), and John Penn (Master 1539). Others portrayed and named are Nicholas Alcock, Christopher Salmon (Master 1552) and William Tilley (Warden 1540, 1546).
According to the diarist Samuel Pepys, the painting was badly damaged in the Great Fire of London of 1666.^[2] It is not clear how much of the original panel was completed by Holbein himself, who died in the year the painting was begun, and how much by others; neither is it known whether those who first added to the work did so under Holbein's supervision. Scholars such as Roy Strong and John Rowlands suspect that the main additions were made after Holbein's death (probably in the last years of Henry VIII's reign), since they are not improvements.^[3] Holbein's cartoon for the composition, later much painted over by other hands, reveals his original conception, but the actual painting departs markedly from it in places, for example in the second row of figures on the right and in the background. The inscription is not Holbein's, though it can be dated to before Henry's death in 1547. The men standing in the second row on the right were added in the mid-16th century by an anonymous painter. The painter and restorer Richard Greenbury reworked the painting in the 17th century, so heavily that he entirely covered the original layers of varnish with impasto.^[4] In the view of Holbein's biographer Derek Wilson, the result is a "disaster": "A lifeless, oversized king dangles the charter from a limp hand while a row (the second rank was added later) of comparatively diminutive recipients kneel in relevant homage. The treatment is archaic and atypical".^[2]
References

1. ↑ Stephanie Buck, Hans Holbein, Cologne: Könemann, 1999, ISBN 3829025831, 128.
2. ↑ ^{a b} Derek Wilson, Hans Holbein: Portrait of an Unknown Man, London: Pimlico, 2006, ISBN 1844139182, 273.
3. ↑ Rowlands, John, Holbein: The Paintings of Hans Holbein the Younger, Boston: David R. Godine, 1985, ISBN 0879235780, 148–49.
4. ↑ Buck, 127–29.