Ulysses is perhaps the ultimate example of a book almost nobody _actually_ enjoys reading, but that many people _convince themselves_ that they appreciate due to certain prestigious literary associations
What do you mean by _enjoy_ here? Do you restrict that word to immediate and accessible pleasures, like eating, or do you think it applies to more drawn-out events, like developing a new skill? The latter is often slow and painful in the moment but pleasurable looking back afterward. If you only include the former, probably few people enjoy reading Ulysses. I think it's much more complicated when you consider the latter.
In Plato's "Republic," he talks about the pleasures associated with the three parts of the psyche: the logistikon (reason), the thymoeides (spirit), and the epithymetikon (appetite). He said that only those people who know the pleasures of reason, in addition to the other two, can judge between the three. He uses this to argue that the pleasures of reason are more enjoyable than the pleasures of fame or the senses, even though most people think otherwise. People who don't know the pleasure of reason may settle for the pleasure of fame, not knowing any better. I think it's possible the pleasure gained from reading Ulysses is like this.
It's a "woke" argument; you can't really argue against it, and that's frustrating. You say, "yeah, but I read Ulysses, and I didn't like it," and they say, "yeah, you must not have read it deeply enough---if you did, you would like it more than you like watching TV or eating ice cream." And they may be right, or they may be wrong. It's like a Buddhist evangelist telling you once you meditate enough, you'll see that they're right about things. You say you did meditate a lot, but they say you need to do it more. You can't argue against it, but you also can't prove them wrong.
I enjoy reading classics. I haven't read Ulysses, but I would say I enjoy reading the Iliad more than almost any other work. When I pick it up and read a few pages, the intensity of emotion is sometimes so strong I get a shiver down my back. This almost never happens when watching television or eating. Those are both great too---balance is good---but I think the pleasure of reading is the strongest for me. It's hard to describe, but I don't think it's just because of some prestigious literary associations---although it is partly because of that for sure. And what's wrong with that? There is something enjoyable about knowing many other people in history have read a book and enjoyed it too. It makes you feel connected to the "great web of humanity." Many people prefer watching football games in crowded arenas to empty couches at home.
I also (truly) enjoyed the Iliad. It is rich with appreciable association.
Having studied english lit in college, I guess I feel betrayed by works like Ulysses. On some level I feel I was promised that immersing myself in the canon to the extent that I could enjoy such a text in the way you described would give me a richer way to perceive reality/life/humanity/whatever. I believe that such is the case with works like the Iliad, the Pentateuch, etc... but for Ulysses, it felt less like connecting myself with more of reality and more like binding myself to the narcissistic culture of literary fiction.
> Ulysses is perhaps the ultimate example of a book almost nobody _actually_ enjoys reading, but that many people _convince themselves_ that they appreciate due to certain prestigious literary associations
I've never actually read it, and don't care to, but isn't it basically a very difficult puzzle (i.e. the satisfaction comes from figuring it out, e.g. the references, allusions, and wordplay packed to an insane density into some bit)? So it can be enjoyable, but most people aren't up to the task (but may still pretend, like you describe).
Edit: I might actually be thinking more of Finnegans Wake than Ulysses.
