I read On the Road in my 20s, a time of life when I was both too square and (usually) too high to make much sense of it. Most of what I remember was the overwhelming pointlessness of it all. I'd already been introduced to Neil Cassidy by Tom Wolfe's Electric Kool-Aid Acid Test, and I was very much aware of the hippies but pretty vague about the beats. I'd go on to Read Cassidy's The First Third and Ginsburg's Howl and even Kerouac's book of sonnets. Howl was the only one that struck me as great writing, with clear echoes of Walt Whitman.
It was easier to romanticize alcoholism before the automobile took over and the carnage on the streets began.