Giovanni di Paolo, in full Giovanni di Paolo di Grazia (born c. 1403, Siena, Republic of Siena [Italy] — died 1482, Siena), painter whose religious paintings maintained the mystical intensity and conservative style of Gothic decorative painting against the trend, progressively dominant in the art of 15th-century Tuscany, toward scientific naturalism and classical humanism. One of the last practitioners of the tradition of medieval painting, he did little to influence the course of art over the four centuries after his death. In the 20th century, however, his tense, often highly dramatic works aroused increasing interest.

Giovanni probably was a pupil of the painter Taddeo di Bartolo, whose style is reflected in his earliest dated work, the Madonna and Child with Angels (1426). In that year Giovanni fell under the influence of the decorative and courtly paintings of Gentile da Fabriano, as can be seen in Giovanni's Madonna of 1427. During the 1440's and early 1450's Giovanni produced his most important works, including the monumental altarpiece of the Presentation of Christ in the Temple (1447–49) and six scenes from The Life of St. John the Baptist. The brooding Madonna Altarpiece of 1463 in the Pienza Cathedral marks the beginning of Giovanni's late period, of which the coarse Assumption polyptych of 1475 from Staggia constitutes the last important work.

Giovanni never left his native Siena, and his work reveals his persistent disdain of Tuscany's progressive painters. He was long considered an inferior artist; his tormented spirituality and expressionist style were little appreciated before about 1920, but from that time his nervous draftsmanship and expressive distortions were considered to have heralded 16th-century Manneristart and the painting of 20th-century Expressionism. Not only the colouristically and formally attractive figures and landscapes of the painter's early and middle periods but also the unrefined forms of the 1460's and especially the 1470's are of interest, as they illustrate the artist's changing vision of the world during the course of his development.

We could not find a portrait og Giovanni di Paolo, so we have used a representation of his Madonn of Humility, circa 1442. It is a Tempera on wood painting that is now hanging at the Boston Museum of Fine Arts.