Thomas Jones was born at Trefonnen near Llandrindod in Radnorshire. At the request of his uncle, he attended Jesus College, Oxford, in order to enter the church, but in 1761 Jones went to London and enrolled at Shipley's drawing school. By March 1763, Jones had decided to pursue landscape painting and persuaded Richard Wilson (1713-1782) to take him as an apprentice. He subsequently established a thriving landscape practice. However, despite his success in London, Jones hankered after Italy.

Jones had long wanted to travel to Italy; a favourite project that had been in agitation for some years, and on which my heart was fixed (A.P. Oppé, ed., Memoirs of Thomas Jones , Walpole Society, XXXII, 1946-1948, p. 37). This may have been heightened by the example of Richard Wilson, whose artistic success had been assured by the Italian scenes he painted on his return to England after six years in Rome in the 1750s. Jones had studied and copied his sketches and studies during his apprenticeship. However, for years his trip to the continent had been thwarted by mounting debts and his parents' disapproval of the scheme and Jones did not leave until October 1776.

Jones was greatly affected by the changing landscape and light as he travelled through France to Italy. After a brief stay in Florence, he arrived in Rome on 27 November 1776. In his lively and informative memoirs, Jones refers to Wilson’s influence when expressing his joy at travelling through Italy and entering Rome, the: new and uncommon Sensations I was filled [with] on my first traversing this beautiful and picturesque Country ... It appeared Magick Land - In fact I had copied so many Studies of the great Man, & my Old Master, Richard Wilson ... that I insensibly became familiarized with Italian Scenes, and enamoured of Italian forms ( ibid. p. 55).

From May 1780 to August 1783 Jones was based in Naples and delighted in the picturesque scenery on the road to Santa Maria dei Monti, a monastery to the east of Naples of which a number of drawings by him are known. He was influenced by the fashionable work of Salvator Rosa, with its treatment of banditti in rocky landscapes. His old friend Francis Towne arrived in Naples in March 1781, and, in his memoirs, Jones describes their trip along the wild road to the monastery : I was able to conduct him to many picturesque scenes of my own discovery, entirely out of the common road of occasional Visiters, either Cavaliers or Artists (Thomas Jones, ibid . p. 102). He drew the road many times- ten are listed in the 1970 Marble Hill catalogue- and further examples are included in the collections of the Tate, the Yale Center for British Art, New Haven and the Rhode Island School of Design, Providence.

Two other drawings of the subject executed on 6 May, the same day as the present drawing, one coloured and one pencil and grey wash, are in the collection of the Whitworth Art Gallery, Manchester. They are of a similar size to the present work and a grey wash drawing (D2002.14) is taken from almost the same spot.

Jones further recorded how he felt about this place in his Memoirs on 2nd June 1781 and another incident which he and Towne had experienced: I proceeded to meet Pars..at an Osteria in the road to S’a M’a de Monti- in this hollow Way is a most beautiful series of picturesque Objects, which I discovered by Accident in one of my perambulations-Here may visibly be traced the scenery that Salvator Rosa formed himself on-Only taking away Pine trees, which were, perhaps planted since his time, and which indicate a state of cultivation not suited to his gloomy mind, with the addition of Water and a few Banditti-And every hundred yards present you with a new sand perfect composition of that Master- When Towne was in Naples I took him with me to see this romantic place, with which he seemed much delighted- but the following whimsical incident put a stop to further explorations at that time and which I forgot to mention in its proper place- Proceeding up the valley whose boundaries contracted more and more as we advanced, increasing in proportion the Gloominess of the Scene; We arrived at a Spot, which might very properly have been termed the Land of Darkness & the Shadow of Death…Here, says I, Mr Towne, is Salvator Rosa in perfection we only want Banditti to compleat the picture- I had scarcely uttered these words when turning round a projection of the rocks, we all at once pop’d upon three ugly-looking fellows dressed in the fantastic garb of the Shirri di Campagna, with long knives cutting up a dead jackAss.-…Towne started back as if struck by an electric shock, strongly impressed, I suppose, with our late adventure on the Coast of Baja-‘I’ll go no further’, says he, with a most solemn face, adding with a forced smile, that however he might admire such scenes in a Picture- he did not relish them in Nature- (ibid. pp. 104-5).

Thomas Jones’s reputation has soared in recent years, notably after the 2003 landmark exhibition Thomas Jones (1742-1803) An Artist Rediscovered (at the National Museum of Wales, Cardiff, the National Gallery, London, and the Whitworth Art Gallery, Manchester) reinstated his reputation as one of the most idiosyncratic and innovative eighteenth-century British artists.

Iolo Williams (1890-1962) was the author of Early English Watercolours (published in 1952), one of the bibles of the field. He left a large part of his collection to the British Museum, but this drawing was held back. He took a keen interest in Welsh matters, serving on the Council of the National Museum of Wales and on the Welsh Committee of the Arts Council.