The blessed (holy) Sisoes was a hermit in the desert of Thebais during the 4th century. He is first portrayed in icons of the 16th century. These portrayals of the holy Sisoes are in the pessimistic, depressed spirit characteristic of the Orthodox East after the Fall of Constantinople. Hosios Sisoes is depicted as a balding,old, man with a long beard standing next to an open grave, sometimes the grave being that of Alexander the Great. Hosios Sisoes is shown speculating on the futility of life and on the inevitable end that comes to all mortals. In this article we present the portrayal of the devout Sisoes at the Monastery of the Virgin Mavriotissa, at the Monastery of Lavra,and the Monastery of Xiropotamos on mount Athos, at the Monastery of Varlaam at Meteora and at Megiste on Castelorizo.