In Venice, Jackson began to work with the chiaroscuro technique. This type of woodcut was originally intended to reproduce the wash drawings of the Renaissance period.3 Beginning in the 16th century, the Italians and Germans became the forerunners in this medium, Jackson revitalized the technique, however, by translating into color woodcuts not only drawings, but oil paintings as well.4 It is in this capacity that Jackson is most known, even through his actual success as a chiaroscuro woodcutter was brief, lasting no more than ten years. 

The first painting that he translated into a woodcut was The Judgement of Solomon by Rubens. It appeared in 1735. Around 1739, Jackson, along with two friends, Charles Frederick and Smart Lethieullier, decided to produce a long series of chiaroscuro woodcuts after Venetian masters.5 The woodcuts, which were to be financed by subscription only, would reproduce work by such artists as Titian, Tintoretto, Veronese, and Leandro and Jacopo Bassano. In total, there were seventeen subjects in the series, on 24 plates. Some prints even had to be done on more than one sheet.

All three of Jackson's prints in the Wake Forest collection are from this series of prints. The Mystic Marriage of St. Catherine, is the sixth print in the series. The subject was taken from a painting by Veronese. The Raising of Lazarus, is the fifteenth print in the series, and is based on a painting by Leandro Bassano. Dives and Lazarus, was the last entry in the series and was derived from a painting by Jacopo Bassano. Each of the three prints was made using four different blocks each inked with a neutral gray or brown.6 Immediately after the success of this first series of chiaroscuro woodcuts, Jackson published his most artistic series, a collection of six prints after the Italian landscapist Marco Ricci. In these prints, Jackson's skill in the medium was at its apex. While he did not attempt to exactly copy the color of the painting, he used many different colored blocks to achieve the final effect. These translated the peaceful and tranquil landscapes of Ricci into rich full color. Another aspect of his craft that made his prints so successful was the technique of embossing. Jackson would take his finished prints and press them over a dry block to create ridges and furrows on the paper, thus adding to the illusion of paint.7

In 1745, Jackson moved back to London, where his career would have flourished had he continued in the path he had taken in Venice. Instead, he took a job designing patterns to be printed on calico cloth. His career as an artist declined from that point. He tried to start a business in the wallpaper industry after the job at the calico factory left him unsatisfied. This venture led to failure also due to lack of public interest, and Jackson led a life of obscurity until his death around 1770. His one notable contribution after his years in Venice was an essay on the chiaroscuro technique. It was published in the 1750s.

Kristin Hicks (1994)