The artist was attempting to continue his development with these two paintings. The traditional disciplines of portraiture and still life painting are displayed here in all their glory, whilst Caravaggio also starts to implement the dramatic lighting effects that became a hallmark of his work. Something such as the clothing worn by this young boy offer some serious technical challenges, but Caravaggio is able to accurately recreate the ripples of material as if an aged master. He was clearly a prodigy who was able to learn quickly once pushed in the right direction. Whilst Boy Peeling Fruit may not be one of his more exciting pieces, there is still plenty to appreciate here from a technical standpoint. In front of the young boy is a wooden table on which he peels a selection of fruit. The artist slightly alters the arrangement of fruit between the two versions, which is one of the most obvious differences.

This version is to be found in the Longhi Collection, Florence, and is slightly larger than the London one. Both pieces are dated at around 1592–1593, but this artwork is believed to have been the first of the two. Because larger there is a little more room to either side of the model, but everything else is much the same. Caravaggio himself would have been in his early twenties at this point, having completed a number of years training under a Milanese painter before then having his personal life disrupted which forced him to move around the country several times. Whilst his technical understanding would have been impacted by these changes, it is clear even at this point that there was something special in the style of Caravaggio, and he already promised much for the future. If we reflect on the styles that had gone before, rather than what came after, we can understand how his approach would be considered so unique and controversial, particularly in his dramatic use of light.

It was not long before the artist would produce some of his most memorable paintings, despite being so new to his career at this stage. He tended to limit the numbers of figures that he used at this point and leave the more ambitious work for later on. Across his twenties he would focus on capturing normal life scenes, such as Musicians, card players or people preparing food as seen in his Boy Peeling Fruit. These portraits were intimate and charming, whilst also developing his aggressive use of lighting that would later become very much his trademark as an artist. Later on he would start to insert religious themes into more of his paintings and these brought about the dramatic poses and activities that most now remember Caravaggio for, such as the iconic David with the Head of Goliath from 1607.