When I read Marx, I thought that his key mistake was a negative view of utopia. That is, utopia is what happens automatically once you overthrow all of the people and structures who are preventing there from being utopia. Just get rid of the capitalists, and the World-Spirit will take care of the rest. The thought that ordinary, fallible, non-World-Spirit humans will have to build the post-revolution world brick by brick, and there’s no guarantee they will do any better than the pre-revolutionary humans who did the same, never seems to have occurred to him.
Kerouac was a staunch anti-Communist, but his beat philosophy seems to share the same wellspring. Once you get rid of all the shackles of society in your personal life – once you stop caring about all those squares who want you to have families and homes and careers and non-terrible friends – once you become a holy criminal who isn’t bound by the law or other people’s needs – then you’ll end up with some ecstatic visionary true self. Kerouac claimed he was Catholic, that he was in search of the Catholic God, and that he found Him – but all of his descriptions of such tend to be a couple of minutes of rapture upon seeing some especially pretty woman in a nightclub or some especially dingy San Francisco alley, followed by continuing to be a jerk who feels driven to travel across the country approximately seven zillion times for no reason.
Like the early Communists, who were always playing up every new factory that opened as the herald of the new age of plenty, in the beginning it’s easy to tell yourself your revolution is succeeding, that you are right on the brink of the new age. But at last come the Andropovs and Brezhnevs of the soul, the stagnation and despair and the going through the motions.
If you have any affection for Beatnik scripture in your heart, you might be offended by the brutally biased and uncharitable review Alexander gives On the Road here, but I thought this part made for an intriguing rest stop. That tends to be my opinion of Beat-style "liberation" as well — it comes off as compulsive, not joyful. As Camus said about the Marquis de Sade's celebration of all things subversive and corrupting, it strikes one as "the fury of a man in chains". It appeals to "the weak characters without power over themselves that hate the constraint of style", as Nietzsche put it. Boundaries must be demolished for daring to exist, until the boundaries of one's own selfhood are added to the ruins. Alan Watts was specifically critical of this unenlightened rebelliousness in Kerouac in his essay Beat Zen, Square Zen, and Zen:
Beat Zen is a complex phenomenon. It ranges from a use of Zen for justifying sheer caprice in art, literature, and life to a very forceful social criticism and "digging of the universe" such as one may find in the poetry of Ginsberg and Snyder, and, rather unevenly, in Kerouac, who is always a shade too self-conscious, too subjective, and too strident to have the flavor of Zen.
When Kerouac gives his philosophical final statement, "I don't know. I don't care. And it doesn't make any difference" — the cat is out of the bag, for there is a hostility in these words which clangs with self-defense. But just because Zen truly surpasses convention and its values, it has no need to say "To hell with it," nor to underline with violence the fact that anything goes.
...In the Dharma Bums, however, we are seeing Snyder through Kerouac's eyes, and some distortions arise, because Kerouac's own Buddhism is a true "Beat" Zen which confuses "anything goes" at the existential level with "anything goes" on the artistic and social levels.
Still, if you'd like to find a more sympathetic perspective on On the Road, here's one at...The American Conservative.