Lolita is supposed to be a challenging piece. In this thread people are discussing the details, but the way I see this and I hope it’s supposed to be seen as is that there is a tremendous contrast between prose and motif. More than any other book ever written IMO. Prose is extraordinarily beautiful, motif is extraordinarily disgusting. It tears the reader apart, inside out. That’s art.

The big difference is that Lolita is a book, so it aims to be published, while most if not all AI Dungeon content stays private and unpublished, so I don't think it's the same.

I just reread Lolita at 45, for the first time since I was 14.

I slogged through it the first time, and didn't particularly enjoy it. All I remember from the first reading is that HH seemed kind of icky. I was barely older than Delores was in the first half of the novel, and I didn't really understand all the implications. I probably skimmed a great deal of the book without paying attention to it. Much of the subtlety of the story and all of the brilliant writing went right over my head.

Then I happened to pick up The Fued, about the friendship and subsequent falling out between Nabakov and Edmund Wilson. It mentioned several times that Lolita was a runaway success, and it made Nabakov famous.

I thought there must be something more to Lolita than I remembered, so I picked up a copy at the library. It was a whole different book. This time, I found the story both riveting and disturbing. On the first read, I knew that what he was doing would be called abuse, but I didn't really understand how he took advantage of her trust and naivety and adolescent rebelliousness. Or how awful it is to dehumanize pre teen girls and characterize them as sexual objects called nymphets.

HH claims to know that he took something irreplaceable from her and ruined her childhood. But - and I think this is why they say he is an unreliable narrator - it's not clear if he really believes what he's saying, or if it's a calculated ploy to garner sympathy.

The writing is incredible. The story is troubling and fascinating, and stayed in my mind a long time after. RIP Delores Schiller.

I have not read the novel, but put it on my reading list a few days back when I discovered it in the best reads list of "The complete Review" [1], which in turn I discovered via the excellent Conversations with Tyler [2] podcast which I started listening to in order a week or two back. I discovered this in a roundabout way via Hackernews (was mentioned in unrelated linked posts multiple times lately)

Why this comment? If you don't know, please check out the fantastic Conversations with Tyler podcast. And if you are looking for a very diverse, entertaining and informative podcast, try it.

Also the "Complete Review". Wow what a website! Proper 90s feel and still delivering value. If you think Lolita is one of the best books to read, you are probably having a similar taste and the reviews might work for you.

[1] https://www.complete-review.com/reviews/nabokovv/lolita1.htm
[2] https://conversationswithtyler.com/episodes/

    No, he was not [great - ] he was typical 
    of a pop culture humorist

You're presenting "great" and "pop cultural humorist" as mutually exclusive terms.

It feels fundamentally incorrect to compare him to writers producing conspicuously deeper and denser stuff.

If you judge him by standards and goals to which he never aspired then I'd agree he comes up awfully short.

Reminds me of the old days when people derided the Beatles and other rock and roll acts because they didn't meet the standards of classical music. Or when people derided e.g. Shigeru Miyamoto because video games didn't measure up to the narrative achievements seen in the best movies.

It's true: The Godfather and Super Mario Brothers are both things that appear on your television screen. Just like Hitchiker's Guide To The Galaxy and Lolita and Finnegan's Wake are all books. Not sure they're trying to be the same thing, though.