> 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-...

Maybe it's that people wish they would dare share that freedom? Escapism from boredom?

The lifestyle does not at all feel pleasant, at least to me. I don't mean it in the sense of regular comfort; these lines describe a tortured man more than they do a 'happy beggar'.

And then there's the chaos the trainwreck leaves behind. I don't believe a man that's truly passionate would have so little empathy for others. If anything, it feels egotistical and self infatuated.

I know many will say those are stereotypes or tropes but having worked with people from 15-28 over the course of many years in a range of roles, it's very much an observation at this point. Orwell especially I suspect comes from required reading.