Although it never really replaced pen and ink as his preferred medium, red chalk was a staple of Guercino’s draughtsmanship, wherein he was particularly influenced by the drawings of Correggio. After his return to Bologna from Rome in 1623 Guercino began to use red chalk regularly, usually to further study the pose of a figure once the initial composition drawings in pen and ink had been completed. As his career progressed, however, his use of red chalk became even more frequent, especially from the 1650’s onwards. Although he remained very busy with commissions until his death in 1666, he seems to have drawn much less, and only a comparatively few drawings - many of which are in red chalk - survive from his last fifteen years of his career.
This drawing may be grouped with a series of preparatory studies for a now-lost painting of Sisyphus painted by Guercino for Count Girolamo Ranuzzi of Bologna in 1636. The painting is described as ‘una figura di un Sisifo’ in the artist’s account book, the libro dei conti, which further notes the sum of 100 ducatoni paid by Ranuzzi on the 28th of October 1636. The price paid for the picture would suggest that the figure of Sisyphus was almost certainly depicted full-length.
Several other drawings of this subject by Guercino are known, all of which may be supposed to be studies for the lost Ranuzzi canvas. Closest in composition to the present sheet is a pen and wash drawing in the Royal Collection at Windsor Castle, which shows Sisyphus supporting the boulder on his back and moving towards the left. Other drawings of this subject show further variations in the pose and direction of Sisyphus. These include a pen and wash study in the Courtauld Institute of Art in London, which alone among the other drawings of this subject does not show Sisyphus carrying the boulder on his back or pushing it up a hill, but rather lifting it from the ground with both hands. Another pen drawing, in the Suida-Manning Collection at the Jack S. Blanton Museum of Art in Austin, Texas, shows Sisyphus turned to the right. A double-sided black chalk drawing, showing an unbearded figure of Sisyphus, is in the Teylers Museum in Haarlem. Two further drawings of this subject appeared on the art market in London in the 1970’s.