This study aimed to scrutinize and analyze the novel On the Road by Jack Kerouac in the light of the political theory of Michel Foucault. The focus, however, would be specifically on the concepts of normalization, institutions and surveillance put forward in his book Discipline and Punish (1995), coupled with some other works that wrestle with the close links of power, society, and institutions. This research seeked to describe the real America in the 1950s, a decade that witnessed both conformism and radicality, represented in the novel. The study pointed out that the novel was a depiction of the American society in the 1950s in which distinct, overlapping institutions did a great deal in restricting the freedom of individuals who seeked liberation and authenticity. The American government draws on the power of the law, police, prison, academia, family, and different other overlapping and satellite institutions, working hand in hand to create a matrix. The concept of matrix, therefore, highlights the nexus through which the normalization and conformity of the individuals are guaranteed, leading to the creation of perfect institutionalized men who are reduced to the level of simpletons. The whole novel becomes the story of some men who advocate abnormality as their credo to live a free life. Quite the contrary, they are transitioned into meek and docile bodies whose identity hinges on being like others in fitting in and following the norms through different dominant fragmenting institutions.