Ulysses is a rough one. There are some novels that are so dense that you have to have already read it through once before you can really read it for the first time. I think Ulysses might take three or four.
I started reading it after hearing Robert Anton Wilson talk at length about why he loved the book. He made it sound amazing. And having read it, and read about it, I get why the people who love it really love it. It's a meticulously crafted, ultra dense, heavily embroidered, masterwork of English literature. You can spend years and years reading and re-reading the book, picking apart layer after layer, and still find new elements to explore, and new threads to pull, which still all end up being perfectly internally consistent. It's really an amazing literary achievement.
But it fucking sucks to read for the first time.
You need like a companion reference book, the Internet, a French to English dictionary for one of the chapters, and a map of Dublin. It's not entertainment; it's a project. And honestly, I've found it a lot more interesting to listen to Ulysses experts explaining the book than it is to actually read the book itself.
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