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Unfortunately, even the stars in the heavens sometimes fall. This is what happened to Jack Kerouac in his final years, and this book is exhibit A.
Kerouac was never the "life is a thrill a minute joy-fest" guy that he's often mistaken for by young people who read "On The Road" and the others for the first time. (Myself included, many years ago) A rereading of his books later in life reveals how sad and confused a man he really was; his novels are a quest, they are not the answer. There are answers in them, but "hit the road and forget everything you were taught by your parents and your teachers" is not an answer he ever gave or intended to give. Kerouac was a profoundly lonely man, so lonely that he let many of his friends treat him like a dog (remember Dean abandoning him in Mexico in "Road") and not only came back for more but wrote some of the greatest books ever written about them.
But his loneliness and confusion truly came home to roost after he became famous. Fame made him bitter and forced him to drink and isolate himself ever more in order to deal with it. He wrote about this in "Big Sur," unquestionably one of his best books, and his power as a writer never left him...but in "Vanity of Duluoz" we see how far he's slipped from the great Journeyman he was two decades earlier. Particularly in the novel's early passages, he rails against modern society and moans over how much better things were when he was young, and it poisons his writing almost fatally. Of course, he is hardly the only writer to complain about the world; one of his greatest influences, Louis-Ferdinand Celine, practically made a career of it, but Celine made it FUNNY, and that makes all the difference. Nobody wants to hear an old man bitch about these kids today, if that's his only point. Celine used his kvetching as a counterpoint to whatever story he was telling, and the contrast comes on like an explosion of energy. Kerouac, sadly, only tells his story to show how much better times were back then than they are now. Worse, in the first sentence of the book he implies that "Vanity Of Duluoz" isn't even meant for us, his faithful readers: it's for his wife. (And judging from the way she kept so much of his writing out of the public eye for decades after he died, it's clear he was preaching to the choir)
I don't know what effect the novel had on the millions of kids who snapped it up in 1967, thinking they were getting another youth-affirming "On The Road" or "Desolation Angels" (another book I drastically misread as a kid) and discovering instead a man their parents' age, complaining about their long hair and their careless, hedonistic lifestyles and how they have used him as an excuse to become worthless bums. Their reaction couldn't have been too happy. It's too bad: a generation who felt he was their christ figure, the one who went out into the world and showed them the way, now finding their buddha telling them to clean up and get lost. And this book, detailing the years 1935 through the end of the War, should have been one of his most joyful, bombastic works: he leaves his hometown, discovers the wonders of Manhattan, meets his great circle of friends, and begins to discover himself as a man and a writer.
But it wasn't to be. He was simply too mired in depression and alcohol to muster the energy needed to give the subject the treatment it deserved. In a roundabout way he did, of course, tackle this time period in his first novel "The Town And The City," and although it lacks the characteristic Kerouac voice it's still an excellent novel, and highly recommended. But it's not the masterpiece that "Vanity" could have been, and that is all the more a tragedy. This book feels like a filler: he'd written about his childhood and his adulthood, now he needed to write about his young adulthood, so he could fill in the gaps in the Duluoz legend and say he finished it. That's just not a good enough reason to write a book. Even when you are---or were---as great a writer as Jack Kerouac.