Five hundred years ago, the southern Renaissance suffered a double blow: only the previous year (1519), Leonardo da Vinci had died, and on Good Friday 1520, Raphael died too – at the tender age of just thirty-seven. Two masters who had already changed the course of painting were both gone.

Yet this year the anniversary of Raphael’s death is likely to pass almost without notice. This is despite the fact that Vasari’s biography, and many painters, have recognised him as one of the most important artists in the whole of the Renaissance, and there’s little dispute as to his influence on painting in Europe and North America for much of the period since.

In this first article of my series to mark Raphael’s death, I consider paintings from around the time that it’s claimed that Raphael became a master in 1500, although there are good reasons to suspect that at that time he still wasn’t painting on his own account, but as an assistant to Pietro Perugino in Perugia and Florence.

Luca Signorelli’s large fresco masterpieces in Orvieto Cathedral were painted between 1499-1502, and are among the major wall paintings of this period. The Damned from the San Brizio Chapel shows how, even when working quickly in this challenging medium, his figures (detail below) are modelled realistically.

Pinturicchio’s wonderful fresco of St Catherine’s Disputation in the Borgia Apartments in the Vatican Palace were painted slightly earlier. According to Vasari, Pinturicchio was a paid assistant to Perugino, who was probably Raphael’s teacher.

Although Sandro Botticelli had apparently ceased painting large religious works by the late 1490s, his paintings from the period include the fascinating Mystic Nativity (1500) above, and his immaculately projected Story of Lucretia (1500-01) below.

Giorgione’s Boy with an Arrow (c 1500) is a brilliant portrait. His subtle modelling of the young man’s face may reflect what he learned from his meeting with Leonardo da Vinci in 1499 or 1500.

Less securely attributed to Giorgione is this famous triple portrait, The Three Ages of Man (c 1500). Its faces are very lifelike and expressive, and are clearly from the hand of a master.

Virgin and Child with Saint Nicasius and Saint Francis of Assisi (the ‘Castelfranco Altarpiece’) from about 1500 combines a fine depiction of the Virgin and infant Christ with two wonderful saintly figures – Nicasius’ armour is spectacular – and an innovative naturalist landscape. The buildings at the upper left are meticulously painted, and there is excellent aerial perspective at the upper right.

Fra Bartolomeo was also active in Florence at the time, then working under his original name of Baccio della Porta. His tondo of the Adoration of the Child from about 1499 is a fine painting of a popular Christian scene, with Jesus’ parents paying their respects to the baby. A variation of the more prescriptive nativity which was often a vehicle for the artist to be less bound by convention, Bartolomeo’s landscape is a joy. In the foreground he has defied seasonal traditions and shows painstakingly-detailed spring flowers, and there is more aerial perspective in the distance too.

Bartolomeo’s The Rest on The Flight into Egypt from about 1500 is a traditional composition showing Mary and Joseph during their journey to Egypt. The more distant landscape is less detailed, but his donkey and palm trees are delightful. This was one of the last paintings which he made before becoming a Dominican friar.

Raphael is believed to have worked with Fra Bartolomeo in 1507, when they were in Florence together. Bartolomeo is thought to have improved his perspective, and Raphael his handling of colour and rendering of fabrics.

Three major influences on Raphael’s style were Leonardo da Vinci, Pietro Perugino, and later Michelangelo, who claimed that Raphael learned everything he knew about painting from his work.

Leonardo’s major work of this time was of course The Last Supper, which is now but a shadow of its former self. Giampietrino’s copy made in about 1520 gives the closest impression today of what the original must have looked like.

Perugino’s paintings from around 1500 are indistinguishable from Raphael’s, to the point where there is considerable dispute over who painted what.

Perugino’s superb Portrait of Francesco delle Opere was painted in 1494. His execution of clothing is characteristically plain, but his face (detail below), hair and hands are lifelike.

Perugino’s fresco in the Collegio del Cambio, showing The Almighty with Prophets and Sybils, was painted between 1497-1500. At the left are the traditional prophets of the Old Testament, and at the right are six sibyls, each clearly captioned.

The faces in Perugino’s Tezi Altarpiece from 1500 might look glum, but they’re each finely modelled.

Until his return to Florence in 1499, Michelangelo had primarily been a sculptor. His earliest surviving paintings both appear to have been abandoned, no reason being apparent.

Michelangelo’s unfinished The Virgin and Child with Saint John and Angels, popularly known as The Manchester Madonna, from about 1497, shows that artist’s skills in modelling flesh and fabrics using egg tempera rather than oils.

His Entombment from about 1500-01 shows a comparable process when working in oils.

Wonderful and realistic these painting may be, but little more than a dozen years later, here’s the mature Raphael, in the Madonna of the Chair (1513-14).

Then there are his frescoes, and those amazing watercolour cartoons: we have a great deal to look forward to in the coming weeks.