He literally drank himself to death and he often banged on and on about boring Catholicism, so you wouldn’t have wanted to hang out with him that much, but his mind was truly forward-thinking and his voice inspired a generation (much to his chagrin). Along with the other Beat poets and writers, Kerouac challenged the literary boundaries of the day (and just about managed to escape obscenity trials like Ginsberg and Burroughs). With creativity often comes eccentricity, and Kerouac was no exception to the rule. An extreme alcohol abuser, his downfall came at the hands of the deadly rye bottle. He did, however, leave behind a legacy of fascinating work. Even if you find his writing style difficult to love, you can console yourself with the fact that he was an absolute BABE.
(For Will — I know Cassady is the one, but hopefully this is a close second… xx)