On the Road reflects and represents postmodernist literature, art, and philosophy, where rules of conduct, expectations, and social norms following World War II were questioned and then challenged. Young people during the end of the 1940s began resenting the rules and expectations of family and society when they felt that there was so much more of the world to explore and experience. Sal and Dean are the epitome of what came to be known as the Beat generation, as they abandon these rules altogether and live life in the moment.

Their “magic land at the end of the road” is in their freedom from mainstream social constricts. Conventional marriage and the pursuit of the typical American Dream of having a house with a white picket fence, a wife, and 2.5 kids may as well be prison for these two. Living in the moment, never knowing where the “road” may lead, is magic for Sal and Dean. Travel and adventure is excitement. Settling down and planting roots is equivalent to stagnation and rot. Ultimately, the line “we never dreamed the extent of the magic” refers to the idea that eventually, a life of total freedom with no order, no stability, and no meaningful relationships can be empty and sad. Dean being described as “crazy” by those who know him throughout the novel, and being abandoned at the end, proves this point.