In all his endeavours Leonardo favoured innovation over established knowledge and the traditions of his craft.
Painting:
From a young age, Leonardo was a hugely talented artist, and his time in the workshop of Verrocchio allowed this talent to flourish. His style, despite being heavily influenced by the trends of the renaissance was intuitive, especially his understanding of colour. After his depiction of an angel in Verrocchio's studio ,Verrocchio vowed never paint colours again as Leonardo 'understood their use better than he did' (Vezzosi p.37). Leonardo's chose to use oil to paint his angel in Verrocchio's Baptism of Christ despite the rest being in the traditional tempera, showing a clearly headstrong nature, and a successful departure from tradition.
Leonardo's first works are characteristic of workshop paintings; The Annunciation is typical in its workshop features; 'the setting of the iconographic programme and the preliminary drawings to the first brushstrokes, the pentimenti and variants, and the assigned contributions of specialists.' (Vezzosi p.34) In The Annunciation the contrast between the faces of the characters, the zealous nature of the architecture and the style of the background show how Leonardo's emphasis on observation, detail and realism did not benefit the inconsistency of a workshop.
Renaissance painting was moving towards 'three-dimensional reality...breaking away from the hieratic symbolism of the middle ages.' (Rachum,1979 p.394). Leonardo's study of geometry and perspective, especially his interest in how perspective affects colour is typical of this renaissance feeling, as is his choice to revive the art of the fresco in The Last Supper. His use of complex compositional devices, cryptic symbolism and observation are however, revolutionary. For example, Leonardo used his close observation of birds to paint the wings of an angel in the Adoration of the Magi, creating this feeling of three-dimensional reality.
The messages in Leonardo's paintings (influenced my mediaeval symbolism) are highly debated and none more so than the Mona Lisa. It has been suggested that the she is his ideal woman, or perhaps the female version of himself. His interest in beauty and the grotesque, and his enigmatic characterisation adds a philosophical depth to his paintings making them more notable than other renaissance painters.
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Patronage:
Traditionally the church had been the greatest patron of the arts throughout the 13th and 14th century. In the early 15th century the demand for ecclesiastical works of art was still high, however as the artists guilds began to commission works themselves, secular works appeared more often. We can see this change in Leonardo's work with his mix of both sacred and secular art.
Around the mid 15th century patronage began to become popular among aristocrats such as the Medici family who used art as evidence of learning. The huge demand for art led to a change in status for artists such as Leonardo, from 'petit-bourgeois artisan[s]' to 'free intellectual workers' (Study Guide p.22). Leonardo's move 'from workshop to princely court' (Study Guide p.22) suited his work, and the variety of his accomplishments may not have been achieved without a selection of patrons.
We can imagine that Leonardo was attracted to court partly due to the chances for 'empirical development' (Study Guide p.22) which would be greater under the patronage of a prince than in a guild. Although it is unknown if the letter to Ludovico il Moro was ever sent, Leonardo's letter was an obvious advertisement; 'I recommend myself in all humility' (Vezzosi p.144). This would suggest that that Leonardo went against tradition and chose his patron rather than being commissioned, possibly due to his interest in the challenge of the Sforza horse.
Under Ludovico's patronage, Leonardo was given the freedom to 'persu[e] his technical studies' (Vezzosi p.77): by the time The Last Supper had