Reynolds' portrait of his friend, Dr. John Armstrong (1709-1779), who was also a poet and essayist, conveys the impression of natural and inherent dignity, a quality essential to any gentleman. The sitter is placed off-center, an innovation of Reynolds that served to modernize the entire state of portraiture at the time. The doctor wears a powdered wig, an essential accouterment of both gentlemen and ladies. Considered obsolete by the late 1740s, powdered wigs continued in favor with the medical profession for a while longer. Dr. Armstrong sat to Reynolds in 1755-6 and again in 1767, which is the probable date of this painting. Another version of this portrait now hangs in the Art Gallery of South Australia, Adelaide. Joshua Reynolds's early interest in drawing and painting came not from his parents-who, while scholarly, had no aptitude for the arts-but from reading treatises on painting in his father's library. At seventeen, Reynolds was apprenticed to the premiere "face painter" of the day and educated himself in Renaissance and Baroque art by traveling to Italy. By the age of 30, Reynolds had set himself up as a painter in London and for the next 40 years, until his death, he dominated British art production and theory. Though criticized and caricatured by students, such as William Blake, for his recycling of Old Master poses, Reynolds elevated the status of British portraiture by ceaselessly applying the principles of history painting to portraits. His Discourses, delivered annually at the Royal Academy prize ceremonies, remain the best-written discussions on the theory and practice of painting in the English language.

Jan Asselyn (1610-1652), a contemporary of Rembrandt's, was a well-known Dutch painter of Italianate landscapes, that is, landscapes based on views of the antique Roman countryside, both real and imagined. He was much influenced by the work of the French artist Claude Lorraine, who also was known for his idealized and glowing views of ancient Italy. Rembrandt frequently used his friends, acquaintances, and loved ones as sitters for his portraits. In this etching, Rembrandt affectionately places Asselyn, whose nickname was Crabbetje, or "Little Crab" because of a crippling affliction to his hand, at his desk as if he has just been interrupted at his work.