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Love Italo Calvino. For people interested in getting into it, "If on a winter's night, a traveller" is probably the best place to start and isn't a tough read.
Agreed, though I'm partial to Invisible Cities. ;)
I, also, love Invisible Cities and would recommend it ...
I find it oddly comforting that the storage provider I plan to use at some point in the future (just getting the hang of ZFS now) loves Calvino. :-D
I understood that reference.
I also believe Invisible Cities to be way more approachable than "if on a winter's night..".

I absolutely loved both, but I think the latter might out off some folks.

But given the HN audience, I feel that "Cosmicomiche" might be a very good choice too!

Came to this thread to also plug Invisible Cities. I love picking up that book, reading a short prose poem and getting the feels of the imagery he evokes.

It's my stranded on a desert island pick, and for good reason.

I recently listened to the audiobook of Invisible Cities, narrated by John Lee, and it was phenomenal. The strange thing is, I actually don't think I would have cared for the novel, had I read it myself, but Lee captured the sort of surreal mood exquisitely, and it was very pleasant to just lay back and listen to, or to have on while walking through a park.
I would attach a note of caution to this - having loved the book myself, I gave my mother (a lady not terribly well-versed in postmodern literature) a copy of Se una notte d'inverno un viaggiatore and it took her quite some time to forgive me; she used the words "pointless" and "stupid" several times in her summary of it!
I also would hesitate to recommend IOAWNAT to your average reader, despite thoroughly enjoying it myself. You have to have a certain patience for literary tricks to really enjoy it.
I feel the different vignettes also provide something relatable to more people than one story would
I absolutely loved "If on a winter's night, a traveller" -- it's in the rarefied company of scant few other works of fiction capable of conjuring such vivid, surreal, and dreamlike worlds -- I can only think of Neuromancer and Paprika off the top of my head.
I love this book a lot. Definitely one to cherish.
My favourite thing about Calvino are his letters. Such great observations, and writing. They are up there with Evelyn Waugh’s letters.
Can you say more about the Calvino and Waugh letters? Do you like them for beautiful prose, for lively gossip, for introspection -- or what?
It's a bit of both, depending on who you're talking about.

I really enjoyed Calvino's letters home from his time visiting the USA. They are entertaining, funny, and observant.

And Evelyn waugh's prose in the letters is lovely, and he can be delightfully bitchy. like you can turn to almost any letter and find Waugh putting something about life vividly, in a way that you can feel. They have this feeling of loneline, combined with misanthropy.

If you enjoy Calvino then Jorge Luis Borges will likely also entertain you. The Library of Babel, for example, is an excellent story.
Makes sense. I read Invisible Cities and really didn't care for it. It seemed decently written but was just terribly uninteresting. I'm trying to work through Borges' Ficciones at the moment and I like it even less.

I wish I could enjoy them!

That would be a really interesting direction for recommendation engines:

"If you didn't like this book, they should absolutely stay away from the following list of books."

I'm reading through a collection of Borges' short stories right now. The Library of Babel was facinating and definitely reminds me of Invisible Cities. One Borges' short story I especially enjoyed was "The Circular Ruins"... you can see some of the concepts echoed in modern media.

I feel that Borges can insert a bit too much superfluous detail (maybe in an attempt to ground the work?), but the results are still thought provoking. Because the prose is old I sometimes need to force myself to re-read passages when my brain decides to zone out... it was written in a different time.

May be Nabakov as well, "If on a winters.." reminded me of Pale Fire (though I thought Pale Fire was better.)
"If on a winter's night, a traveler" and "Invisible Cities" are probably his most known works but I highly recommend "Mr. Palomar", it's very small and easy to read but truly a mindbender.
My favorite Calvino book is Cosmicomics. It's a collection of his stories that deal with a scientific principle that he weaves into a beautiful fantasy story!
If you're open to non-fiction or more elliptical writing on aesthetics, Six Memos for the Next Millennium is certainly worth checking out as well. A must-read for artists in any discipline!
I recently finished a history podcast inspired by Six Memos for the Next Millenium, called Six Memories of the Last Millenium.