Leonardo Da Vinci is not known to have done many portraits of men, and it is argued that if this is indeed his painting, then it is the first he did of a man.

Much debate has existed since the painting seems to lack in documentation and there is even no record of anyone having commissioned it. Some have even argued that this is his least appreciated pieces, yet it is ironically the best preserved works.

Controversy has existed over the years on who actually painted this piece. Some of the names fronted include Bernadino Luini, Giovanni Antonio Boltraffio, Leonardo Da Vinci and Ambrogio de Predis. Its controversial nature does not end here, with there being issue on the identity of the subject on the painting.

The assumption was that it was the Portrait of Ludovico il Moro, who was the benefactor to Leonardo, an assumption held until 1905. However, after the painting was commissioned for cleaning, a sheet of music and the inscription CANT…ANG… were revealed, which settled the issue that the man on the painting was actually a musician.

The two most important musician in Milan during this period were Franchino Gaffurio and Josquin des Prés. However, since most of Da Vinci's were filled with puzzles, no one really nailed down exactly who the subject was.

Another main reason why this painting has been shrouded in mystery is that its lower parts are unfinished, it is unsigned and some additional painting has been added over the years.

One of the main reasons why this work has been attributed to Leonardo da Vinci is the characteristics which are evident in his portraiture pieces.

For example, he leaves the background in shadow, his subjects are half or slightly more in length and he usually portrayed his subjects at three-quarter views for easier identification.

However, as with his other pieces where he employs a three quarter view for easier identification, most of his subjects are usually hard to identify such as in this case. Leonardo da Vinci is known for using dark backgrounds that have strong contrasts of dark and light.

The Portrait of the Musician also has the familiar feature of square hands, which is identical to the portrait subject in the Lady with an Ermine painting. The eyes of the character in this painting are also similar to those of the Virgin of the Rocks painting.

Leonardo was of the belief of on emphasising human character, which is common in most of his works. In this painting, the musician seems to come from a dark and gloomy background which will greatly suggest the subject as full of character. By having the musician come from a dark and gloomy background, it emphasizes his character and he seems more real.

The musician can be seen to be concentrating a lot in his music sheet, especially given that his face is full of expression. However, it is not clear whether he is composing, reading or waiting to perform it. In his typical Da Vinci signature move, he does not paint his subject looking down, but instead chooses to let the audience see his eyes and their expressions, which is like inviting us to see deep within his soul.