A black chalk drawing of a demon, partly kneeling and twisting.

The aspect of the demon vaguely resembles those in Michelangelo's Last Judgment in the Sistine Chapel, and Bernard Berenson (Drawings of the Florentine Painters, no. 1750) thought the drawing might be an enlargement of a lost original sketch by Michelangelo, for the demon pulling a rope in the bottom right hand corner of the fresco. Johannes Wilde (Popham and Wilde 1949, no. 445) argued a closer resemblance to the Triton drawn on a wall of the former villa of the Buonarroti at Settignano (a work attributed to Michelangelo himself in eg. C. Bambach, Michelangelo. Divine Draftsman & Designer, 2017, no. 37).

The style of the drawing is close to that of Sebastiano Filippi, called Bastianino (c.1530-1602), a Ferrarese artist who spent several years in Rome where he developed a distinctive Michelangelesque style; compare the celebrated drawing in Christ Church, Oxford (JBS 908). The drawing could conceivably have been a study for his masterpiece, the Last Judgment in the apse of Ferrara Cathedral (1577-1581), which is indebted to Michelangelo’s fresco of the subject.

The drawing is inscribed on the verso ‘Michel Angolo 5.2’ in the hand associated with the English seventeenth-century dealer William Gibson, whose inscriptions and characteristic ‘price codes’ can be found on at least 51 drawings in the Royal Collection. Jonathan Richardson the Elder explained Gibson's pricing system whereby the second figure is the unit - 1 for a shilling, 2 for half a crown, 3 for a crown (5 shillings) and 4 for a pound (20 shillings); a price code of 5.2 would indicate that the drawing was priced at 12½ shillings.

Like many other drawings with an English seventeenth-century provenance, the top corners of this sheet have been cropped, perhaps to be placed in a decorative mount. This cropping could be indicative of a particular collector or could represent a more general fashion adopted by English collectors at that time; some 14 of the 51 drawings in the Royal Collection with Gibson inscriptions have been cropped in this way (though none of the drawings with Lanier marks have been cropped), and a further 29 Italian Renaissance drawings without collectors' marks have been shaped in the same manner. It is likely that all these drawings were acquired for the Royal Collection in the seventeenth century, most probably during the reign of Charles II.