Philosophy of language has come to occupy a central place in the scheme of philosophizing since the analytic philosopher up until this moment. Philosophy of language has two main schools – the ordinary language philosophers and the ideal language theorists. Wittgenstein belongs to the ideal language because he is a logical positivist. In his ground breaking Tractatus Logico-Philosophicus, he pens down his picture theory which holds that all propositions should picture reality. In his thought, language should be symbolical, logical and perfect for it to be properly understood and cherished. His theory has generated lots and lots of appraisals and criticisms, but one would not have expected that Wittgenstein would be the greatest critic of his work. He critiqued his picture theory in his language game theory where he upheld the diversity of language, and placed emphasis on the pragmatic nature of language. This paper offers an in-depth study of his picture theory, and most especially his critique of the picture theory as expressed in the language-game theory.