On the road can seem underwhelming to people today, just like Citizen Kane is "meh" for most people. You have to put it into context.

As I said in another comment, Kerouac was smoking pot, doing hard drugs, eating bulgur and tofu, hiking, practicing buddhism, driving around the country, having orgies (including with men) IN THE 40s AND 50s. The context in the 40s and 50s was vastly different from today, but even from the 60s and 70s. Religion was still controling everyhing. You need to understand that nobody was even close to having Kerouac's lifestyle at the time, although it seems pretty normal today or even in the 70s. About 5 people created a whole movement that would later become the hippies and today's hipsters.

Hunter S. Thompson did the same thing, but 30 years later. While his stories are good, he invented nothing.