Holloway enrolled in the Royal Academy Schools in 1773. From this date until 1777 he exhibited a range of works at the Royal Academy, including portraits in crayon and oil, seals and engraved gems. However, it was as an engraver that he made his living. The largest project he worked on was the publication in English of J.C. Lavater’s ‘Essays on Physiognomy’, which was published in five volumes between 1789 and 1798. Holloway had overall control of the series of engravings that amounted to 800 plates in total. He executed some 300 himself. In 1800 Holloway embarked on a folio edition of engravings after the full-scale designs for tapestries by Raphael, which were then at Windsor. This led to Holloway’s appointment as historical engraver to the king.