1949 seems to have been the crucial year.  I’m still reading Windblown World, and it has been fascinating to watch the development of Kerouac’s thinking and writing.  In ’49, in the midst of getting The Town and the City ready for publication, the writer whom we know as Jack Kerouac is emerging from his chrysalis.  The careful, thought-out (though not always coherent) writing of ’47 and ’48 is giving way to the free association, the made-up words, the intoxicated-with-words French-Canadian Yankee yawp that was Kerouac at his height, before he destroyed his mind with alcohol.

Someone I read not long ago, but whose name unfortunately escapes me, makes the very astute observation that with artists, so often the very thing that helps them break on through to the other side is also the thing that kills them.  Maybe what happened in ’49 is that Jack had finally drunk enough alcohol.  By 1960, the year Tristessa was published, he had clearly drunk too much.

Here’s an interesting quote from 1948:

Also, I believe in sanewriting, as opposed to the psychotic sloppiness of Joyce.  Joyce is a man who only gave up trying to communicate to human beings.  I myself do that when I’m drunk-weary and full of misery, therefore I know it’s not so honest as it’s spiteful to blurt out associations without a true human effort to evoke and give significant intelligence to one’s sayings.  It’s a kind of scornful idiocy.

I hope he’s talking about Finnegans Wake, but even so, what a shame.  What’s an even greater shame however is that he himself fell into precisely the trap he describes.  Even more in his journals than in his books, it is clear that Kerouac absolutely despises almost everyone but his fellow beats.  Then again, there is the famous quote in which he says that he is not a beat at all, but a Catholic.

Fact is, Kerouac was one terribly confused, guilt-ridden, frustrated, and contemptuous individual.   Which makes it easy to see why he found the teachings of Buddhism so appealing, and also why he was such a lousy Buddhist.

But the tortured sot did have a way with words, and he did manage to see and express a discontent that a certain number of his fellow Americans were also feeling at the time.  Fortunately, he did break through to another side; unfortunately, he also got lost there.  Fortunately, he left some signposts behind for the rest of us.  One of the truest pieces of advice he ever gave is in On the Road, when he talks about the time shortly after he’d met Neal Cassady, who’d come to him begging for advice on how to write.  ‘What do I know, says Jack, ‘about writing, except that you have to stick to it like a benny addict.’