If on a Winter’s Night a Traveller gives the reader the impression that there must be a system at play and gives up some of its secrets easily. However, there remains a persistent feeling, after reading each section, that there are other connections - threads of deliberate meaning - between them all that slip through your fingers as you desperately try to clutch more and more fragments passing by.
It's one of my favorite books precisely because it generates this feeling and led me to Perec's Life: A User's Manual among other fantastic works.
As a fan of Calvino I will say that If on a Winter’s Night a Traveller is somewhat more enjoyable after you've read a bunch of other Calvino, since it has a somewhat cheeky, self-referential feel and the more you sympathize with the author the more you may like it.
Numbers in the Dark is very good as a place to start.
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Italo Calvino, The Art of Fiction No. 130 (1992) - https://news.ycombinator.com/item?id=26395898 - March 2021 (28 comments)
The Penguin Book of Oulipo review – writing, a user's manual - https://news.ycombinator.com/item?id=21869669 - Dec 2019 (2 comments)
Italo Calvino, The Art of Fiction No. 130 (1992) - https://news.ycombinator.com/item?id=21340794 - Oct 2019 (29 comments)
The Movies of My Youth - https://news.ycombinator.com/item?id=10151334 - Sept 2015 (5 comments)
Cybernetics and Ghosts (1967) - https://news.ycombinator.com/item?id=9001508 - Feb 2015 (1 comment)
It's one of my favorite books precisely because it generates this feeling and led me to Perec's Life: A User's Manual among other fantastic works.
https://news.ycombinator.com/item?id=35197000 (March 2023)
For people who may be unfamiliar with this (excellent) connection: https://en.wikipedia.org/wiki/Oulipo
Numbers in the Dark is very good as a place to start.
I'd definitely suggest starting with these. His short story work is beautiful.