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The Left Hand Of Darkness managed to be both groundbreaking and popular.

https://en.wikipedia.org/wiki/The_Left_Hand_of_Darkness

Not disagreeing with any of the sibling comments - but imnho her latest series "Annals of the Western Shore": "Gifts", "Voices" and "Powers" is also worth mentioning.
I would almost certainly start with 'The Wizard of Earthsea'. Incredibly approachable and likely her most influential work. Plus Ged is awesome.
If you want to get a sense of her mature utopian and anthropological thinking, then read "Always Coming Home". It's not a conventional novel but more of a series of observations on a post-apocalyptic society in California. The framing device is of an anthropological investigator from another time/place interviewing people in the society or hearing their stories and poetry (she also wrote good poetry). It even has accompanying music which she collaborated on with Todd Barton.
Depends on your speed. If you want a slow but epic burn, Left Hand of Darkness. Something faster action novella, Lathe of Heaven. And the OG Harry Potter tale, Earthsea series. It won’t be time wasted with any of these.
"The Left Hand Of Darkness" and "The Dispossessed" are great back-to-back.
Her short story collections are quite accessible. If you want to dive into the Hainish cycle, _Four Ways to Forgiveness. Or for a mostly Hainish but more diverse set of stories, _The Wind's Twelve Quarters_.
I've only read her first three Earthsea books and some of her short stories, but The Wizard of Earthsea had a big impact on me.

Also, one short story of hers that I really like is available online:

http://www.lightspeedmagazine.com/fiction/the-island-of-the-...

On a side note, I noticed some of the best book "choices" I've made came when I was able to read a couple snippets. Just enough to get my curiosity going.

It would be cool if Amazon released some of the most highlighted passages for some of these stories. I feel like it would do more for discoverability than just recommending book titles.

Yeah, I'd like to see some improvement too. Simply asking strangers who you think may be like you feels weak.

My favourite weird recommendation was The 2020 Commission Report¹. I watched a guy miss his stop on the train home because his thoughts were so taken by it. Seemed like a good enough reason to pick it up ;)

1. https://en.m.wikipedia.org/wiki/The_2020_Commission_Report_o...

Ohh. Thanks for the recommendation. Just reading about the Wikipedia article had me entranced.
That's a cool idea for a browser extension -- pull quotes off Wikiquote and inject them into the item listing
I love The Left Hand of Darkness, but I think it’s definitely a slow burn, for what it is worth. It is worth sticking with it, though :)