The Serjeant Painter was an honourable and lucrative position as court painter with the English monarch. It carried with it the prerogative of painting and gilding all of the King's residences, coaches, banners, etc. and it grossed over £1,000 in a good year by the 18th century. The work itself involved painting the palaces, coaches, royal barges, and all sorts of decorations for festivities, which often had to be designed as well. The actual involvement of the serjeant painters in this gradually declined. The post itself fell out of use in the 18th century, after a period when "fine art" painters were appointed, and expected to supervise rather than execute decorative painting, for a good salary.

The post of serjeant-painter came into being with the appointment of John Browne in 1511–12. In the time of Henry VIII, they seem to have acted as at least foremen for the actual workers; from 1527, better artists were made "King's Painter", like Lucas Horenbout. They may have also painted portraits. George Gower was appointed by Elizabeth I in 1581, and in 1603, James I appointed John de Critz at £40 a year (a good salary) together with another - first Leonard Fryer, and from 1610 Robert Peake the Elder. Gower and de Critz were reputable artists, as was Peake, and these appointments mark a stage in the divorce of the position from the actual work involved. For Anthony van Dyck the position of Principal Painter in Ordinary was devised, at a retainer of £200 p.a.; this continued until Queen Victoria and was nearly always given to a portraitist. By the 18th century most of the work was done by assistants. In 1720 Sir James Thornhill was appointed Serjeant Painter and, in 1757, William Hogarth.

The last known holder was James Stewart, of whom no records are available after 1782, though it is not clear whether the post was ever actually abolished. In a patent issued on 7 May 1679 for Robert Streater Jr, a list of previous serjeant-painters is given, including "John Decreetz & Robert Peake" as joint-holders of the post. De Critz was given the post in 1603 but is first described as sharing the office with Leonard Fryer, who had held it since 1595. Robert Peake was appointed jointly with de Critz in 1607, or 1610. A payment made to de Critz in 1633 shows that he was paid a retainer of £40 a year.

The role of the serjeant painter was elastic in its definition of duties: it involved not just the painting of original portraits but of their reproductions in new versions, to be sent to other courts (King James, unlike Elizabeth, was markedly averse to sitting for his portrait) as well as copying and restoring portraits by other painters in the royal collection, and many decorative tasks, for example scene painting and the painting of banners.

The lines of demarcation between the work of the serjeant-painters and that of other artists employed by the court sometimes needed clarification. A patent drafted in 1584, but apparently never signed, gave the serjeant-painter George Gower the monopoly of "all manner of portraits and pictures" of the Queen, "excepting only one Nicholas Hilliard, to whom it shall or may be lawful to exercise and make portraits, pictures, or proportions of our body and person in small compass in limning only" (Hilliard's monopoly was signed). At the time, Nicholas Hilliard was the leading artist in limning, the painting of portrait miniatures. This was regarded as the highest form of painting, while easel painting "in large" was still associated with interior decorating. In 1606, Hilliard seems to have trodden on the toes of the serjeant-painter John de Critz when he put himself forward to paint the tomb of Elizabeth I, claiming that he had "skill to make more radiant colours like unto enamels than yet is to Painters known". Hilliard reports in a letter to Robert Cecil, 1st Earl of Salisbury, that the recently appointed de Critz had reminded him that any painting of the royal tomb was "within the Serjeant's patent".

Horace Walpole provided information about some of the tasks de Critz performed in his Anecdotes of Painting in England, which he based closely on the notes of George Vertue, who had met acquaintances of de Critz and his family. In particular, Walpole quoted from a scrap of paper, a "memorandum in his own hand", on which de Critz wrote bills for jobs completed. On one side was his bill for work on a sun-dial:

For several times oyling and laying with fayre white a stone for a sun-dyall opposite to some part of the king and queen’s lodgings, the lines thereof being drawn in severall colours, the letters directing to the bowers guilded with fine gould, as alsoe the glory, and a scrowle guilded with fine gould, whereon the number and figures specifying the planetary howers are inscribed; likewise certain letters drawne in black informing in what part of the compasse the sun at any time there shining shall be resident; the whole worke being circumferenced with a frett painted in a manner of a stone one, the compleat measure of the whole being six foote.

On the other side is a demand for payment for work on the royal barge: