alt Hacker NewsI'm not very familiar with Kerouac, but I've at least heard people talk about it. It was far less impactful, but reading the Scott Alexander review, the very first thing that comes to mind is SLC Punk! Of course SLC Punk! makes its message pretty explicit, and by the end the main character learns that living so hedonistically was always selfish / immature / destructive / etc.
When I was a kid, I was very sad for the last half of SLC Punk! Like so many stupid kids, I was sure that I was oppressed and my angry instincts had some sort of real defiance and valor to them. And of course, just like the movie, a bit of life experience and maturity revealed the lie. I rewatched the movie recently as an adult (~late 30s) it was a totally different experience. The end of the movie felt a bit like a mercy. (which I'm sure is what the director intended)
I say this only because I've never heard people talk about Kerouac in this way, but I also think the last time I heard anyone talk about Kerouac was back in college; back when we could still lie to ourselves about the nature of (stupid, teenage) rebellion. Back when we had no inkling just how selfish or privileged we were.
I very much relate to the SLC Punk experience. The movie that came to mind for me as I was writing my comment was Dazed and Confused, it brings back that same feeling. One of the big questions I have now about Kerouac and On The Road is how much self-awareness he found. My understanding is that he was an essential part of the vanguard of American counter culture, a flawed prophet that can still be appreciated on some level.