In his likening of Shakespeare's Hamlet to a sponge which absorbs all the problems of our time[i], the Polish poet, critic, and Professor of Literature Jan Cott implies that Hamlet will continue to be contemporary no matter what time has passed. The timelessness of the play derives in the first place from its liability to re-interpretation and re-contextualization in different political and social circles by virtue of its humanitarian, existential and metaphysical implications. The skeptical philosophy background of "Knowledge and suspicion" seems to have had its profound impact on Shakespeare that he can be seen more like an ideological thinker and philosopher than simply a playwright. In Hamlet the Bard problematizes the philosophical nature of the human individual and puts into question the individual's relation to matters of decision-making, fate and willpower. The play puts into true moral test the nature of the human soul as a plot which moves the action forward, and simultaneously reflects on questions of relevance to knowledge and doubt. This article seeks to explore points of intersection between Hamlet and the philosophy of doubt, which lingered over the Renaissance and throughout the seventeenth century. The Central questions evoked revolve around two postulations: whether certainty about knowledge is reachable, and whether Prince Hamlet and ourselves are the ones who choose our destinies or whether our fates are pre-determined and we cannot change anything but yield in full subservience. Of all Shakeseare's plays Jan Kott wrote of Hamlet in particular: "Hamlet’ is like a sponge. Unless it is produced in a stylised or antiquarian fashion, it immediately absorbs all the problems of our time." His chapter on Hamlet focused on a Polish performance just after the end of Stalinism (Stalin hated this play, of course). Kott wrote, "here on the public stage was what Hamlet meant in 1956, there and then: ‘It was a political drama. Everybody, without exception, was being consistently watched… unequivocally and with a terrifying clarity.’