During the late fourteenth century, artists began to use paper more and more to explore their ideas for the design of paintings and sculptures, rather than simply to copy or record finished works of art. This exploratory type of drawing offers a vivid and intimate glimpse of the artist creatively thinking on paper.

In preparing a composition, artists first drew quick sketches, usually in pen and ink, in which they formulated general ideas rather than focused on details. An example is Leonardo da Vinci's fascinating double-sided sheet that includes an exquisite small sketch for an allegory on the fidelity of the lizard, and the stage design for a musical comedy (17.142.2). Another of Leonardo's double-sided sheets combines an exciting array of ideas for different projects: a figure of Hercules probably intended for a sculpture, some scientific illustrations of the flow of water around obstacles, and a tiny figure of a man sheathing or unsheathing a sword (2000.328a,b).

In the next steps of the creative process, artists investigated the poses of the figures from life models. The earliest such extant studies date from the first years of the fifteenth century. Using the medium of silverpoint on pink prepared paper to obtain delicate tonal effects, Filippino Lippi posed a male studio assistant to stand in for the figure of a bound Christ or Saint Sebastian, in order to observe the figure's chiseled nude musculature (36.101.1). In contrast, Raphael's sheet of studies of an infant (1997.75) attempts to capture his energy and delightful gestures, and the red chalk medium serves to imitate the soft tonal effects of his dimpled flesh. Artists then integrated the results of studying the figures from life models into a summary design of the composition, in order to pull together the figural arrangements with the lighting effects and setting. Raphael's Madonna and Child with the Infant Saint John the Baptist (64.47) offers a fairly rough summary study of their pyramidal grouping, while Titian's poetic study of two satyrs in a landscape (1999.28) concentrates especially on the transforming effects of light and atmosphere.

As a final step, artists drew cartoons (full-scale drawings). These were especially necessary in painting frescoes on moist plaster, for the enormously difficult medium of fresco demanded that artists paint quickly, one plaster patch per day, before the moist plaster and the water-based colors set in a chemical process. The monumental cartoon by Francesco Salviati (2001.409) is boldly rendered with black chalk and white highlights in the final size of the figure in the fresco painting, and the main outlines around the figure are incised with a stylus for the transfer of the full-scale design onto the moist plaster.

During the late fourteenth century, artists also began to work out the details of their commissions for paintings, sculptures, and buildings with their prospective patrons by drafting legally binding contracts. These contracts often included a drawing as an attachment in order to explain the details of the design that was expected and that would be agreed upon by the two parties. A number of drawings were also more generally produced as demonstration pieces (modelli) for the patron's approval and for the workshop's use, and these were often carefully modeled with pen and ink and were fairly complete regarding the iconography. These types of demonstration drawings for sculptural projects usually illustrate the architectural framework of the monument, as is seen in the designs by Jacopo della Quercia for the Fonte Gaia that was orignally meant for the Piazza del Campo in Siena (49.141), and by Michelangelo for the tomb of Pope Julius II, intended originally for Saint Peter's Basilica in the Vatican (62.93.1).

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