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The purpose of this paper is to confront Schelling's and Nicolaus Cusanus' ideas and thoughts (though we do not know if the former ever read the latter's works). Such a confrontation is of interest because both philosophers deal with the same issue (each with his own means): the connection between identity, posited as supreme ontological principle, and totality. To address the problem, it seems that both thinkers developed an "iterative" concept of identity and used the same paradigm of the image so as to envision the status of finite things. The comparison between Schelling and Cusanus allows us to realize that the way each of them conceptualizes unity does not entail a rejection of all forms of multiplicity but gives pride of place to the notion of singularity.