The purpose of the paper is to examine some episodes from the historical „controversy” between symbol and allegory triggered in the period of Enlightenment. My starting point being Walter Benjamin’s critique of the Enlightenment and Romantic conception of symbol in his book on German Trauerspiel I attempt to show how the notion of allegory put into new use by Benjamin becomes the key concept of Paul de Man’s deconstruction. De Man makes it into an interpretative tool which undermines the totality of meaning while uncovering the subtle and games language plays with itself. The other episode of that controversy is Freud’s psychoanalysis featuring the opposition between „allegorical”, idiomatic meaning of dreams or other phantasmatic scenarios and the universal meaning of cultural symbols that find their place in psychic artefacts.