Gianfrancesco Penni
Born in Florence to a family of weavers, Penni entered Raphael's workshop very early in his life, and collaborated with him on several works, including the famous Rooms of the Vatican Palace, as well as the frescoes of Villa Farnesina, both in Rome. Heinrich Wölfflin and some other writers credited him with the entire execution of the Raphael Cartoons, with Raphael only creating the initial design, though more recent writers believe Raphael did much of the work himself.
Raphael
His first documented work was the "Baronci altarpiece" for the church of Saint Nicholas of Tolentino in Città di Castello, a town halfway between Perugia and Urbino. Evangelista da Pian di Meleto, who had worked for his father, was also named in the commission. It was commissioned in 1500 and finished in 1501; now only some cut sections and a preparatory drawing remain. In the following years he painted works for other churches there, including the "Mond Crucifixion" (about 1503) and the Brera "Wedding of the Virgin" (1504), and for Perugia, such as the "Oddi Altarpiece". He very probably also visited Florence in this period. These are large works, some in fresco, where Raphael confidently marshals his compositions in the somewhat static style of Perugino. He also painted many small and exquisite cabinet paintings in these years, probably mostly for the connoisseurs in the Urbino court, like the "Three Graces" and "St. Michael", and he began to paint Madonnas and portraits. In 1502 he went to Siena at the invitation of another pupil of Perugino, Pinturicchio, "being a friend of Raphael and knowing him to be a draughtsman of the highest quality" to help with the cartoons, and very likely the designs, for a fresco series in the Piccolomini Library in Siena Cathedral. He was evidently already much in demand even at this early stage in his career.