Infinite Jest, Herzog, Ulysses, Things Fall Apart, The Magic Mountain, Zeno's Conscience, The Sun Also Rises, Underworld, ...

Trying to read Ulysses is like trying to learn Haskel, but maybe more difficult.

Also, I would add The Crying of Lot 49 to your list.

I think it's a common misconception and negative stereotype that things like Ulysses or Bebop are difficult. They're just an experience. Calling them difficult would be like calling Yosemite difficult (and lamenting that you don't fully get all of the rock formations, geological history, social history, flora, fauna...etc).

Anyone interested in tackling Ulysses in 2014 would benefit greatly from Frank Delaney's ongoing Re:Joyce podcast, in which he "unpacks" the book a paragraph or so at a time. He's been at it for three and a half years and is almost through "Calypso", the fourth chapter. That's an advantage for a first-time reader, as it gets you through the (deliberately ponderous and self-indulgent) "Proteus" stretch in Book I.

http://blog.frankdelaney.com/re-joyce/

Ulysses is a singular book: Well-worth it if you love language, or for that matter almost anything about life as it is lived.

A book so complicated that it requires a podcast to make sense of it is not the best formulation of whatever message it is trying to bring.

But then I admittedly have not gotten past page 200 of ulysses in the three times I've tried, so that may be coloring my perception.

No, the "teach me about the world and myself" is not a criteria for being a good book, quite the opposite. It is not because a book teaches you something that it is good, it is because it is good that it teaches you something.

But why or how is it good, then? Well, usually because the writer is a good writer (but not always, some books have no writers, or are good despite their bad writers).

And a good writer is just someone who has a very itchy scar somewhere and would die if not using writing as a bloodletting.

Ok, I'd still like some examples if you have any. I think that'd help me better understand.

that boils down to "good books are made of good writing, which is created by good writers, and good writers feel strongly about the things they write about"

Personally here's a book that changed my life : The Game. But I think it's gonna be frowned upon here.

I don't see the world or even myself in the same way since.

It's simply a good book that gives a model/framework for self-improvement and how attraction between men and women work. It's still a model, it doesn't apply all the time, but it gives a certain insight and lets one see patterns whereas before, one sees only this behavior and that behavior and has problems to connect the dots. It is a model to unlearn (or at least: put into perspective) all the other models you learned about flirting in the past (mainly bullshit flirt guides, advice from girls, and Hollywood movies).

I think it's more than that, it's also an amazing story. It's not just another book about self improvement.

For me it was The Prophet by Khalil Gibran.