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The play Macbeth is a Tragedy written by Shakespeare in the Elizabethan Age while Milton’s Paradise Lost is an epic poem of 12 Books written in the Puritan Age. This work compares and contrasts the parallels in situations and settings between Shakespeare’s Macbeth and Milton’s Paradise Lost. Additionally, although one is a play and the other is a poem, both texts are shown to resemble in the plot as well as the particular personality traits of their characters. A deeper deconstruction of some of these, with particular emphasis on the trait and the effects of ‘ambition’, are analysed in this work. Starting from a low point at the beginning of the respective texts, its characters’ ambition drives them to commit more and more heinous crimes lead them down a path of destruction and death. Their tricks and manipulations further fuel their unchecked lust for power until they lose all perspective of morals, ethics, honour and values, making them not only the Anti-Heroes, but, in fact, the Villains in their own stories.