One of a group of studies of devils preparatory to Saint Michael vanquishing the Rebel Angels painted on the interior façade of the Florentine church of SS. Michele e Gaetano in 1653, A. Barsanti and R. Contini, Cecco Bravo, Pittore senza regola, exhib. cat., Florence, Casa Buonarotti, 1998, p. 116. The fresco was already neglected in the late 18th Century and was eventually destroyed after 1820.
Thirteen drawings of falling devils relating to that fresco are in the Louvre (C. Monbeig Goguel, Dessins baroques florentins du musée du Louvre, exhib. cat., Paris, Musée du Louvre, 1981, nos. 81-2) and further drawings are in the Uffizi (A. Barsanti and R. Contini, op. cit., nos. 45-6), in the Bibliotheca Marucelliana, Florence, in the National Gallery of Victoria, Melbourne, and in the National Gallery of Scotland in Edinburgh.
The intensity of this devil's head is close to that of Cecco Bravo's famous series of drawings of Sogni (one sold at Christie's London, 7 July 1998, lot 13 and others in the Willumsen Museum, Fredericksund, and elsewhere). In an early description of the fresco, F. Bocchi and G. Cinelli (Le Bellezze della Città di Firenze, 1677 (ed. 1974), p. 19) comment that 'Cecco Bravo claimed that when he was painting his Saint Michael ... he felt the devil to be alive and spoke to him freely and with familiarity'.
The strips of coloured paper laid down on the drawings' borders are typical of Italian 17th and 18th Century mounts. A number of drawings with the same mounts and inscriptions by the same hand are in the Uffizi, see Il Seicento Fiorentino, exhib. cat., Florence, Palazzo Strozzi, 1986-87, nos. 2.160, 2.237 and 2.329.