In this essay, Milton’s Paradise Lost and Marlowe’s “Doctor Faustus” are compared as critical texts that address the dominant religious orthodoxy of their respective histories. The conflict of free will and Christian faith are set into different sites of contradiction; however, Marlowe and Milton both present the question of individuality directly against the assumption of absolute faith in God. In this paper, the two documents are analyzed to read for the ways sympathies for individuality are expressed and the ways God’s judgments are scrutinized in terms of justice and humanity.