I've recently been reminded of a few favorite short stories, and discovered some new ones, that swirl around themes of existence, engineering. order, systems, computing, and information.
None of these are deep cuts; they are well known among sci-fi readers and short story lovers. But I thought I'd compile the ones I love nonetheless.
The Last Question is Asmiov's best story, and everyone knows it (Asimov included). A later story, The Last Answer, is also excellent and related only indirectly, through an existential theme. It's worth noting that Answer by Fredric Brown is likely an (uncited) inspiration (it was written a few years prior). Lastly, a Douglas Adams fan will surely recognize the famous Last Question parody from Hitchiker's Guide.
Nearly a period piece; bizarre and subverts expectations in terms of writing and style, while having a plot that appears cliche, except that the cliche originated with this story. In other words, purely original, but the ideas have entered collective consciousness such that they seems well worn.
Boy oh boy Ted Chiang is exciting. Story of Your Life is another short of his that provided the plot of the excellent movie Arrival. Apart from that, this is likely his best-known story, and my favorite.
Particularly interesting in the context of GPT-3 et al.
Confession: This is not actually one of my favorites. It's nominally as thought-provoking as any other story here, but it just doesn't stick in my mind the same way as some others. Nonethless, it's enjoyable and so thematically close to some of the other stories that I had to include it in this list.
Perhaps you've heard of the Handicapper General? It's hard to believe that this was written in 1961. In fact, it's a good reminder that we are prisoners of our own experience and societal issues that may seem novel are not new at all.