In this article we attempt to compare two important works from different periods but with the same subject matter: the pictorial representation of the Last Judgment. The first, the work of an anonymous painter of the fourteenth century (about 1320), decorates the parecclession of the Chora Monastery in Constantinople, also known as Kariye Djami. The anonymity of the artist was customary in his time and by no way it implies that he was a mediocre painter. The second work is the celebrated last Judgment in the Sistine Chapel in Rome, executed by Michelangelo in the sixteenth century (about 1540). Through the detailed description of the two masterpieces we highlight their similarities and differences. For example, in both almost the same compositional principles are followed; a similar layout with parallel bands or tiers that enhance the central figure of Christ, the focus of interest, extends over a most spacious surface: in the Sistine Chapel the Last Judgment occupies the entire east wall, in the Chora Monastery it adorns the cupola to the east of the dome and extends over the pendetives, the northern and half of the southern drum of the dome. However, while in the Constantinopolitan work the spectator is imbued with the symbolism and the idealism that the entire Greek art radiates, in the Roman painting he experiences the almost tangible, animated representation of the entire spectrum of human and earthly feelings.