Maybe it's because I never had my On the Road phase, but this review on Kerouac I always found really strong:
> On the Road is a terrible book about terrible people. Jack Kerouac and his terrible friends drive across the US about seven zillion times for no particular reason, getting in car accidents and stealing stuff and screwing women whom they promise to marry and then don’t.
> Jack Kerouac’s relationship with Dean can best be described as “enabler”. He rarely commits any great misdeeds himself. He’s just along for the ride [usually literally, generally in flagrant contravention of all applicable traffic laws] with Dean, watching him destroy people’s lives, doing nothing about it, and then going into rhapsodies about how free-spirited and unencumbered and holy and mad and visionary it all is.
https://readscottalexander.com/posts/ssc-book-review-on-the-...
And in Zen and the Art of Motorcycle Maintenance, they don't even manage to do any motorcycle maintenance!
(I think people have misunderstood the appeal of the book, probably because the psychological conditions of the mid-20th century are unrecognizable. It is significant that the book is from 1957, a whole decade before Easy Rider and the general transition period centered on 1968)
It must be so exhausting to go through life only enjoying things that match one’s up-to-the-minute current moral views. I guess all biographies of influential people are basically out, as being successful in 1000BC or 1500AD required one to do things considered unethical today.
It feels a bit like religious fundamentalism with a different veneer.
I have had my on the road phase when I was around 18 when I read the book but I did not vibe at all with it. I found all the characters highly unlikeable and couldn't help to think that I much better friends, even my wildest ones. But I wasn't wild enough I guess because I actually managed to finish the book, like a well behaved schoolboy.
The deep pockmarks in Scott Alexander's hands
left from so strongly clutching his pearls
will take an eternity to de-dimple.
I did have a Kerouac phase (in college, read all his work and many of the other beats) but came to the same conclusion as this reviewer a few years later. It actually really hits the nail on the head.
Also -- I liked them because I was 19. It was a phase reflective of a moment in time for me. That didn't last, so neither did the idolization of that way of life. I started seeing it as sad, especially when you learn how most of their lives ended.