Interesting take, and I can see that as well. That said, I think alternative forms of media like television, video games, and potentially even social media shorts might be able to recreate portions of that experience.

The medium (books, tv, social media, video games) shouldn't matter so long as it is forcing you to challenge preconceived notions.

And that's where I think the current malaise lies - reward systems that are basically min-max with extra steps will not reward challenging or risk taking content. That's the downside of removing friction.

For many CS/math people, this is what Godel Escher Bach was. Read it at age 15 and it opens your mind to this alternate higher universe of amazing ideas.

I don't think most people who own it have actually read more than a chapter or two, but that's ok. Its essential function turned out to be to inspire and unlock a part of the young intellectual mind.

How paradoxical. Man rejects books about rebelliousness because of negative social proof. Over time has increasingly sophisticated collectively-held ideology about why they are bad. Initially, it apparently was about pure artistic merit, a notion since more or less purged. No matter, the justification meanwhile morphed into something else. One might start to think there was actually something to these "forbidden" tomes, now that they are actually (again?) frowned upon by your Lit professors.

Not saying these are universal masterpieces. To every reader slightly different books will be the most enriching. It's true that at a certain age, there is often a transformation from the young adult interest in self to interest in the wider world. But the self is still what humans have, so it's not like it ever ceases to be relevant for one's experience.

While there is something romantic in finding a subculture, even one just slightly adjacent to the mainstream, [being] more chancy, on reflection I'm glad we no longer have it like that. (In fact, we probably regressed a little bit because of the decline of open internet and Google, and the move to group chats.) But today's youth can find and pirate whatever they want. The establishment is founded more on pure concentration of money and financing for legacy institutions, not actual technological hurdles like it used to be.

Yeah, one of my fond dreams from my youth was of _The Glass Bead Game_ and the possibility that such a system could exist, but these days, no one seems to have heard of Hesse.

The precursors would include Piers Anthony (unrereadable, not least for being terribly misogynist and worse),

But along with Tolkein the "spec fic"' on this list might well include Robert Heinlein (and Frank Herbert if he wasn't mentioned).

Heinlein made precisely one of the promises well articulated: that beyond the apparently venal and banal world of one's own surroundings, a richer adult world, indeed at a "higher pitch."

In Heinlein's case this was a somewhat narrow world reflective in an oblique way. of some real-world problems: exclusivity. In his world, a particular set of political and moral ideas (his ideas about sexuality were are also arguably not re-readable) is often collectively arrived at by his precocious characters, who trade knowingly in it, and have a relationship to the normies that is at best charitable or pitying and often caustic.

It was quite a thing to realize as I aged past 16 that he was painting not just a fantasy, but one which was not just not awaiting around the corner, but literally un-realizable,

because the attitudes and behaviors of his characters however good on the page, are completely absent from lived experience—at least, in anything like the way he promises. It's not just that the ideas and value he enshrines are not widely held; it's that they cannot are arguably not sustainable and are almost certainly incompatible with both individual human psychology and potential... and do not and cannot serve as a foundation for the sorts of exclusive societies he imagines.

In many of his earlier works, progressive sexually liberated intellectually liberal but socially formal cultures have naturally, inevitably, become the norm; and humanity has thereby thrived, leaving behind what he contends is its primitive imperfections.

By his later works, he tacitly acknowledged and indeed made central the struggle between the embrace of such values and social and political structures; and a "normie" culture permanently mired in those imperfections.

Moving here to the Bay Area in the 90s I met a lot of people who had encountered these ideas at the same impressionable age; and who like me, to some real degree expected to find (or make) communities adopting many of those ideas.

Indeed there's probably another more somber essay here: tracing the history of those specific ideas from their source, in a through-line to crypto-utopian effective altruism and its dream of libertarian city states unshackled from the normie masses, down into the ugly mire of resurgent openly racist zero-sum class war fascism and the shrill ideas of Curtis Yarvin.

It is easy to imagine disappointment then anger at the non-existent (sexually liberated) libertarian gun-owning utopia of genteel Heinlein,

metastasizing into what its adherents understand as Randian "Will" to make it so. To build, damn the consequences, move fast and break things—most of all the ugly banal venal complexities and inherent pluralism and ambiguities of the normies' world.

It must seem like a noble fight, in pursuit of a shared vision,

but it's a vision that as described ITA is fundamentally and only an adolescent one.

Humour, or at least the attempt at it, seems to be the main thing.

I read Catcher in the Rye as a teenager. Even then I perceived some of that rebelliousness as trying too hard. A reminder that life at school sucks and many things are meaningless is hardly an epiphany.

Those books come from the times when the counterculture barely started getting commercialized. The market niche for the angsty teenagers, who self-identify as intellectuals, is quite filled with YA, movies and games. One modern outlet that comes to mind is the rationalist community - it provides a distinct perspective to view the world, together with the feeling that you see it better than others.

While I appreciated the author's thoughts on a canon of books I have also imbibed at an impressionalbe age, I can't help notice the strange fixation on how the author is perceived socially by consuming certain books. Sure, when one is young and emeshed in the schooling social hierarchy (and the years after one leaves school), one may care deeply of their book consumption and their mask of intellectualism.

Maybe I'm just getting old, but doesn't everyone at a certain age stop caring about which books they read, and how the reading of certain books is perceived by others?

There's a lot I can relate to here... and also some things I disagree with. I read a lot of these same authors as a bored and slightly alienated Gen-X teenager, and agree with a lot of what the OP says about their appeal. Network TV and pop radio offered a limited range of perspectives, attitudes, philosophies, and role models. There were hints of a more anarchistic, rebellious attitude that one could find on TV, but it usually required staying up late (eg. to watch David Letterman). Or one could buy cassettes by bands like The Smiths, to get a more off-kilter take on the traditional themes of pop. These authors fulfilled a similar function. However, I do think it's a bit unfair to lump them together like this, because they were as different as they were similar, and I disagree with the author's view that one should outgrow them.

hmm, I thought Vonnegut and Kerouac were still OK among the elite thinkers, and Orwell on his way to being important again due to the state of the world and all that.

I do notice no mention of Sam Clemens or his pen name.

Finally, is Ginsberg really in the white middlebrow canon - and is Gertrude Stein as important as assumed.

Maybe my tastes are too scattershot to be able to be able to have a well-defined brow of any sort, but I'm just not sure I believe all the categorizations made.