The comparative structural analysis of some of Michelangelo's best known works of sculpture including the Duomo Deposition and the Pietà Rondanini as well as the Brutus and several full length figures, and also of Michelangelo's preparatory drawings for these works and of his studies for the Annunciations and for a Crucifixion and a Resurrection, show that the master constantly reckoned with the conceptual implications of laterality which he defined not according to the left and right of the figure represented but according to the subjective experience of the viewer. In addition to the conventional moral implications of the right and left as metaphors of positive and negative connotations respectively, the polarity also seems to be endowed with special temporal meanings: the left is often associated with a retrospective view of the past and the right with the anticipation of things to come.