The Italo-Byzantine style started hundreds of years ago, dominated early medieval age painting in Italy and it was known as the “models of composition and the gold background,” (Kleiner). Cimabue was the first painter that started to break away from the Italo-Byzantine style through his “Madonna Enthroned with Angels and Prophets,” painting. Approximately thirty years later, Giotto, a student of Cimabue, became the first Renaissance painter, a pioneer in pursuing a naturalistic approach to representation based on observation, according to the Art Historians. Giotto masterpiece “Madonna Enthroned” marks the end of the Medieval painting and start a new revolution to art. “Madonna Enthroned with Angels and Prophets,” by Cimabue and “Madonna Enthroned” by Giotto appeared to be very similar, but many details are shaped differently. Let try to figure out the similarities and differences between the two painting that changed human history.Cimabue, is also called Cenni di Pepo or Cenni di Pepi, was an Italian painter from Florence, Italy. He was strongly influenced by the Italo-Byzantine style, but has broken away with more naturalism and humanism in his works. Spencer called Cimabue the last great Italian artist in the Byzantine style. His paintings were depicted with more real-life proportions, perfect shading and motioning painting that set him on a higher art level than the rest of the other artists. Cimabue passed his art techniques to his student Giotto, who later became the first Renaissance painter that created a more radical break from the past than Cimabue according to Giorgio Vasari.Giotto, also known as Giotto di Bondone was the first Renaissance painter that break away the Byzantine style even furthermore than Cimabue. “For almost seven centuries Giotto has been revered as the father of European painting and the first of the great Italian masters” (Murray). Giotto regarded as a pioneer in pursuing a naturalistic approach to representation based on observation. According to the “Gardner’s Art Through the Ages”, Giotto’s aimed to construct a figure that has substance, dimensionality, and bulk, while Cimabue’s figure does not have those qualities. Giotto used tempera medium and gold leaf on wood surface to set his painting to the next level. The shift significantly shown in the “Madonna Enthroned with Angels and Prophets”.Looking at the “Madonna Enthroned with Angels and Prophets,” by Cimabue and “Madonna Enthroned” by Giotto side-by-side, the viewers can recognize that both paintings are pentagon shape, gold background, and on the same Madonna and the child, which represent as Virgin Mary and Jesus. The word Madonna means “My Lady” in Italian. By examining a little closer, the viewer can infer that all the angels and the apostles are gathered around Madonna and the baby to share the joy. Both paintings used the same tempera method and gold leaf on wood to paint the background. Similarity, both paintings were painted in Florence, Italy, and now, both are locating in the Uffizi Gallery at Florence.If we look at Cimabue’s painting, it seems very flat, lack of deep and has a problem with Madonna being accessible. The viewers only able to see her from a far distance, rather than walking up to her or she walks down because the apostles are in between Madonna and the viewers. If the viewers pay a little more attention to the angels around Madonna, they all look at many directions in Cimabue’s painting, while the angels in Giotto’s painting all look up at her. Madonna seems very friendly and regales in Cimabue’s painting. The drapery of her clothing making her appear very thin and tall, however, Madonna appear curvier in Giotto’s painting because her clothes look very loose and short. By comparing the size, “Madonna Enthroned with Angels and Prophets,” appeared larger by 1.02 meters by 0.76 meters. Giotto paint “Madonna Enthroned” in 1310, thirty years after Cimabue’s painting, appears more humanistic, the higher level of shading and coloring, more opening space, and seems more naturalism. Giotto’s painting marks the end of the Medieval painting in Italy and the beginning of a new naturalistic approach to art.Although “Madonna Enthroned with Angels and Prophets,” by Cimabue and “Madonna Enthroned” by Giotto have painted nearly a thousand year ago, but according to Kiddpanther: “both painting showing their influences and contrast shifts of the Italian art style through its generation.” From the same root of Italo-Byzantine style, Cimabue was the first artist to started break away that style, later, his student, Giotto was able to break away the Byzantine style even furthermore than Cimabue did. Thanks to Cimabue and Giotto paintings, art historians are able to understand more in deep of the revolution, life style and religious from the past.