The outcome of reflections and experiences during Ludwig Wittgenstein’s interregnum imbued a remarkable difference between what is historically termed the early and late philosophy of Wittgenstein. Wittgenstein was no doubt one of the towering figures of the analytic movement in the twentieth century with two remarkably different paths. Interestingly each of paths had great impact in the analytical movement. This essay argues that though Wittgenstein followed different paths, he never lost sight of his contention that language held the key to our understanding and depiction of reality. In other words it is only through constructs of language that we can have a representation of reality. Either as pictures or as game, language helps us in perceiving the world and communicating our perceptions. To this end, this essay explores the singularity of purpose through a critical analysis of the difference between his views in both periods thus enriching understanding