Fantasy Stories That Don’t Romanticise the Past

The big counterexample is Discworld, where a significant portion of the books are about making the world (or at least Ankh-Morpork) better through either social or technological progress. There's even one specifically about moving away from the hidebound prejudices of the past (Thud!).
Guards! Guards! has a bit about wanting a king again instead of the Patrician, because of the old glory days. That idea gets pretty short shrift.

As for other fantasy books that don't glorify the past: Shannara (where the past is truly grim), the Gentlemen Bastards (where there's not much history given in the books) and Artemis Fowl (where people have different ideas about what bits of history were good).
 

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Anyone got more to add?

I'd mention that theatrical productions of fantasy stories happen with more frequency, and most, if not nearly all, place their performance in spaces that examine or push against the romanticized elements of the original work; this goes beyond setting the time period to a less distant time that's more familiar for the audience.

It can include bold casting choices (e.g. Prospero as a woman, to look at how mother-daughter relationships differ in terms of interaction from the traditional father-daughter one featured in The Tempest, even when the language is kept the same), or by changing the setting, highlight certain themes in the work, or offer new lenses for the audience to look at the work with.
 
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I'm a little surprised we've gotten this far without any mention of Game of Thrones. In the first book, the Dothraki, lead by Drogo and Daenerys, conquer some people. Daenerys had been largely portrayed a sympathetic character, she's been abused herself and expresses concern about the wellbeing of others, and she stops the Dothraki from doing what a lot of conquering armies often did in the aftermath of battle.

Daenerys is genuinely confused when a woman she saved betrays her. This woman explains to Daenerys that rather than being her savior, she's responsible for the death of her friends and the destruction of her people. It kind of sets the tone for the whole series where we see how destructive wars are. Our heroes play at being noble, but at the end of the day it's all pretty ugly.
 

The First Law series.
I’d say it’s so grimdark, HBO show, “everyone sucks, always”, that it cannot count. It doesn’t look fondly or kindly on anything, to a degree that felt very forced by the time I was done reading the second one (that I read, idk if it was strictly in order but I think so, it’s been a long time), and even in the first one the whole climax, the “twists”, the whole vibe felt like a r/writingprompts story where the prompt was “write a compelling story where literally no one that is remotely likeable or in any way good can be said to achieve anything or get any part of what they try to achieve, and the worst of a bad bunch win.”

Saying it’s an example of not romanticizing the past….is technically true, but ultimately kinda a bad example IMO.


Lol sorry rant over
 

Have you read any historical crime fiction!?
Yes. Plenty.
As for "medieval" romance, I would say there is nothing medieval about it. It's just feel-good fiction that has been around since stories were first invented, and is found in most popular fiction, irrespective of dragons. Most people read for escapism, and the past is a popular place to escape to. It isn't any more fantasy than it is any other genre.
No, medieval romance is a specific genre, out of which modern fantasy has directly grown. And medieval romance was a lot more than just "feel good fiction." It involves specific tropes that are now staples of fantasy. This is not exactly a hot take; it's pretty obvious.

"Medieval romance" is not a catch-all term, as you seem to think.
 

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