Benvenuto di Giovanni di Meo del Guasta is first documented as a young painter in 1453, when he worked alongside Vecchietta, who was probably his teacher, on the fresco decoration of the baptistry of Siena. In that same year he painted a now-lost work in the chapter house of the Compagnia di Santa Lucia in Siena. Benvenuto is mentioned again in 1460, along with Vecchietta and Francesco di Giorgio, as being in the debt of Siena's Opera del Duomo; around this date he must have painted the baptistry fresco series of stories from the life of Saint Anthony of Padua as well as a panel, The Miracle of Saint Anthony (Munich, Alte Pinakothek), which according to a recent proposal was probably part of a lost predella with scenes painted by Vecchietta and Francesco di Giorgio.
The first dated work by Benvenuto to come down to us is an Annunciation and Saints (1466) in the church of San Girolamo in Volterra, for which the artist also painted a Nativity (1470) and a predella with stories of the life of Christ, now in the Volterra Pinacoteca. Also of 1470 is the Annunciation panel in the church of San Bernardino in Sinalunga. During this period Benvenuto's artistic idiom, which in his earliest phases clearly shows the influence of Vecchietta and the naturalistic vision of Domenico di Bartolo, acquires its individualism. This is due in part to his prolonged contact with two North Italian miniaturists who were active in Siena, Liberale da Verona and Girolamo da Cremona. Under their influence Benvenuto's noble, classical forms congeal to a hard, intensely lit, brightly colored, and glassy consistency, inserted into solidly balanced compositional structures. Masterpieces from this sharply defined, immaculately surreal world are the triptych from Montepertuso (dated 1475, now in the parish church of Vescovado di Murlo, near Siena), the Borghesi altarpiece in the church of San Domenico in Siena (1475-1477/1478), and the triptych in the National Gallery, London (1479).
In the 1480s Benvenuto was commissioned to prepare designs for the floor decoration of the Siena cathedral and miniatures for its choir books (now in the Libreria Piccolomini) and for those of the monastery of Sant'Eugenio near Siena (now in the library of the abbey of Cava dei Tirreni). For Sant'Eugenio he also realized the large Ascension of Christ altarpiece, signed and dated 1491 (now in the Pinacoteca Nazionale in Siena; the predella panels are at the NGA), a work in which his severely classical language, charged with a latent expressive passion derived from northern painting, achieved its most intense results. In the following years his works show a simpler, more schematic compositional structure and more pleasant, sometimes sugary expressions, in part because of increasingly frequent collaboration with his son, Girolamo di Benvenuto. Nonetheless, despite the identical composition of two large panels of the Assumption of the Virgin pictures, both of 1498 (one formerly no. 10.148 in the Metropolitan Museum of Art, New York, signed by Benvenuto, and the other in the Museo d Arte Sacra in Montalcino, signed by his son) the styles of the two artists are clearly distinguishable. At the beginning of the sixteenth century the older master's works reveal incrementally the exhaustion of his creative imagination and a recourse to tried and true formulas from the past, as in the case of his last signed work, the Madonna and Child with Saints in the church of Santa Lucia in Sinalunga, dated 1509. [This is the artist's biography published in the NGA Systematic Catalogue]
 See Luciano Bellosi, Francesco di Giorgio e il Rinascimento a Siena 1450-1500; exh. cat. Chiesa di Sant'Agostino, Siena; Milan, 1993: 39-47.
Fredericksen, Burton, and Darrell Davisson. Benvenuto di Giovanni. Girolamo di Benvenuto. Malibu, 1966.
Kanter, Laurence B. "Benvenuto di Giovanni." In Painting in Renaissance Siena 1420-1500. Ed. Keith Christiansen, Laurence B. Kanter, and Carl Brandon Strehlke. Exh. cat., Metropolitan Museum of Art, New York, 1988: 300-315.
Alessi, Cecilia. In Francesco di Giorgio e il Rinascimento a Siena 1450-1500. Edited by Luciano Bellosi. Exh. cat., Chiesa di Sant'Agostino, Siena. Milan, 1993: 518-519.
Bandera, Maria Cristina. Benvenuto di Giovanni. Milan, 1999.
Boskovits, Miklós, and David Alan Brown, et al. Italian Paintings of the Fifteenth Century. The Systematic Catalogue of the National Gallery of Art. Washington, D.C., 2003: 106.