Notably associated with the German-born portrait painter Godfrey Kneller, Simon had an active career that spanned at least three and a half decades, and was regarded as one of the mezzotint medium's most prolific masters of his generation, along with the older contemporaneous engraver John Smith.
[6] Early in the 18th century,[b] Simon moved to London and began working in mezzotint, quickly adapting to the market demands;[8] his earliest known prints were published from Cross Lane, Long Acre, during the middle years of Queen Anne's reign.
[27][28] Aside from portraiture, Simon took biblical, historical, and decorative subjects; alongside the Raphael Cartoons, these include Christ Restoring the Blind Man's Sight by Louis Laguerre, Four Elements by Jacopo Amigoni, Four Seasons by Rosalba Carriera.
[31] There are mezzotints by Simon made likely of his own invention, or after that by unknown authors; these include a portrait of the Russian statesman Alexander Danilovich, Prince Menshikov;[32] The Judgment of Paris, a mythological subject;[33][34] and A Winter Evening's Conversation, a satyrical print.
[40] In the 20th century, the English authors Malcolm Charles Salaman and the 3rd Baron Killanin credited Simon for bringing a "fresh artistic sensitiveness" and, overall, a French influence into the mezzotint medium, respectively.