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I've read a few Murakami books, but always find myself underwhelmed. Every few years I try again — everyone else loves his books, so clearly I'm missing something — but I'm yet to find one that I really enjoy. (I have the same problem with Rushdie, so perhaps I just don't get critically acclaimed literature?)

Besides Kafka on the Shore, The Wind Up Bird Chronicles, and What I Talk About When I Talk About Running, which of his books would be the best way to get into Haruki Murakami?

I think Kafka and Wind Up Bird are pretty representative. If you've given them a shot, it's probable you just don't like his writing. I agree that Norwegian Wood is different enough that you could try it, or Wild Sheep Chase, but I don't see particularly why you'd like them if you don't like the others. I'm a big Murakami fan, but I think he's a little like Rush, either you really like him or you dont understand why people like him. You're not the first person I've heard say this.
Furthermore, it's OK to not like things. :) It's why we have so many things to choose from.
I absolutely loved "Hard Boiled Wonderland and the End of the World". It's just downright bonkers.
I second this. It was the first of his books I read, and it is quite different but I think exemplifies what I liked about the writer. A melancholic stroll through a surreal scenario, but unlike some of his stories I felt this one had a resolution.
I was initially annoyed by the main character, but was loving it by the end. I think the weirdly neurotic narration was reflective of the character's bizarre split consciousness; the alternating stories between the main character and the End of the World were such a fascinating way to present this.
It's funny, the alternation was my least favorite part (I love the book). Not that I can think of a better way to make the story work. But personally I'm annoyed by constant back and forth like that. 18Q4 is similar, and of course many other authors do the same thing. Personally I find it overused. The book is still great in spite of it though.
"Representative" isn't "best". Try Hard Boiled Wonderland and the End of the World or Norwegian Wood. Men without Women feels like the best short stories to start with.

Then Wild Sheep Chase, then you've read enough for 1q84.

I really liked South of the Border, West of the Sun - it's a rather short novel and IMO pretty focused thematically. And then, of course, Norwegian Wood is a must-read.
I finished Norwegian Wood a couple weeks ago, it reminded me a lot of South of the Border. SOTB only gets a touch of surreal towards the end; beyond that, they're similar in their relatively down-to-earth view of the protagonist's struggle with interpersonal interactions.
I definitely got the feeling when I read Rushdie that I was just reading a Pynchon who was a little too eager to let you in on all his very clever little jokes.
I've read many of his books and short stories over the years, and would recommend "Underground", about the 1995 Aum Shinrikyo sarin gas attack on the Tokyo subway.

The English translation is, I believe, much shorter than the original Japanese, but I found its intimate descriptions of everyday Tokyo life contrasting with the terror of that morning powerful reading.

Great! I also agree. One phrase always stuck with me, when talking about the leader of the cult, Murakami said, paraphrasing, "imagine the bloodbath of internal conflicts that must need to happen to give rise to someone like that". For some reason, I've always remembered it. "Bloodbath of internal conflicts" was a line that always stuck with me. :P ;) xx ;p

Also, I recommend getting hands on the very early (and short) English translations of, "Hear the Wind Sing", and "Pinball 1973" -- just really strange, bizarre and cool. Like a distilled pure essence of all his works to come, but these were (I think) his first two. You can sort of see all his themes, style and everything in those first two. Really great! :) ;p xx ;p

Seconding pinball 1973
I have read and remembered exactly one of Murikami's stories, and it hit me like a giant earthquake: the short story "Super-Frog Saves Tokyo." I cannot recommend it enough.
There is a very recent animation movie by Pierre Földes that kind of remixes his main tropes, but with Frog as the central figure intertwined with the guy and the cat from the Wind-up Bird Chronicles: https://en.m.wikipedia.org/wiki/Blind_Willow,_Sleeping_Woman.... I really enjoyed it, it’s like a mashup of his main works.
Just read the Wikipedia entry for this book and can recommend it as well: https://en.wikipedia.org/wiki/Underground_(Murakami_book)
I mostly agree with this review.

I absolutely loved "What I Talk About When I Talk About Running," which is basically a memoir as well.

But this book wasn't nearly as engaging.

If you're more interested in a memoir than the craft of writing, skip this one and read Running.

I found King's book on writing more useful too.

Now I just want to reread Bird Chronicle. May Kasahara was hilarious.
May Kasahara was entertaining but that Manchukuo story is absolutely something else. Probably one of the most striking stories I ever read in the world literature. "Wind Up Bird Chronicles" is such an excellent book.
If I ever read the book again I’m skipping that part entirely. Far too vivid and horrific for me.
I recently saw "Woman in the Dunes" ("Suna no Onna", 1964) and it felt like a close cousin of "The Wind-up Bird Chronicle". Weird movie.

You can find the whole thing on YouTube (U.S. region anyway).

Trailer: https://youtu.be/7kX4h_sEBiI

I have an INKling to reread HBW+EOW.
I think that's my favorite of his. It's got all the elements of a good Murakami story - all the usual human relations stuff in the main story and all the weird stuff in the "end of the world" part, and the constant feeling that there's lots more to understand. It's hard to put into words, but I'd say it's a much tighter story with the same effect as some of the ones that go on a lot longer.
i read kafka and 1q74, colourless tsukuru tazaki, and wind up bird chronicle but put hbw/eow down halfway thru and got too busy to finish it. maybe this is a sign to do so
Don't overlook the earlier books like Norwegian Wood, Wild Sheep Chase, and The Elephant Vanishes. Easier reading than the thick books and fun and beautiful.
A fun bit of trivia about Norwegian Wood: for some unfathomable reason, the French translator decided to translate it as "La Ballade de l'Impossible" (The Ballad of the Impossible). The one Murakami novel named after a universally famous song was translated to... That.
In Spain it became "Tokyo Blues". I think probably the reason was that Norwegian Wood was not a so so so popular song over here for the mainstream public (excluding Beatles fans). It was not "Yellow Submarine" or "Hey Jude" level. I am pretty sure if the song from the novel was "Hey Jude" or even "Eleanor Rigby" they would have kept it.
Sure, it's not their biggest song. But from what I've seen, most of his novels have been translated with a relatively faithful title (say, "Kafka sur le rivage" for Kafka on the shore). It's only this one which gets a completely new title.

And I don't think it's even some bizarre copyright issue, as it could easily be translated in Spanish as "Bosque noruego", while the original song title, if translated, would be closer to "Madera de Noruga". It's not like he titled directly after the song in Japanese either...

Dance, Dance, Dance which is a “sequel” to Wild Sheep Chase is my favorite, followed by WUNC and then HBW/EOW.

Total aside but has anyone found good Murakami-esque movies or TV Shows? Parts of The Leftovers actually gave me the same feeling, especially “International Assassin” and the surrounding episodes but am happy to hear others.

There's quite a few directors who credit Murakami as an influence on their works.

Rian Johnson credits HBW+EOW as an influence on Looper.

Wong Kar-wai says he took inspiration from Murakami in Chunking Express.

David Mitchell is clearly influenced by his works (worth reading if you're a Murakami fan). His novel Cloud Atlas got a film adaptation with Tom Hanks and some other big names.

In anime, Satoshi Kon and Makoto Shinkai have said Murakami was a big influence on them. There's also Haibane Renmei which was influenced by HBW+EOW (IMO not worth watching). Probably plenty more anime with similar styles because it's a more suitable medium for the kind of surrealism in Murakami's novels. You might like Psycho-Pass, GITS, Lain which share some of the same elements of Murakami's works.

A Wild Sheep Chase was the first present I bought my wife when we were dating. Great book.
A wild sheep chase is probably my second favorite after HBW+EOW.

I've not read Norwegian Wood but have watched the film adaptation of it, which I found a bit disappointing. I'm sure the read is much better.

I enjoyed one or two of his books, but some of them I just couldn't get into.
This has got to be a simulation. Too many coincidences.
Somehow I doubt one of the essays in this book is about how to write female characters in a way that isn’t creepy, and reductively sexual.

Murakami’s writing is undeniably creative and interesting, but the way he writes women undermines the whole thing and I find it weird he gets a pass for that so much.

Why does it undermine the whole thing? Isn't he allowed to be flawed? Does every author need to perfect and morally ideal?

I would suggest take him as he is, including his flaws.

I dunno, I feel like if you're a novelist, it behooves you to do at least a passable job of representing half of human existence in your works. I see that more as an incredibly low bar to pass, not being 'perfect and morally ideal'. For me a flawed author is someone with wooden dialogue or unsatisfying endings, not a lack of interest in representing certain kinds of human beings authentically and seriously.
I respectfully disagree. I prefer honest self expression above meeting any bars at all.

A reader who is engaging critically with a Murakami book can't help but be creeped out and shocked by the dreamlike scenarios, including, as you mentioned, women that don't seem real, but also, most characters don't feel real. Intimate scenes are empty, unemotional, disconnected from reality.

They are expressions of deep self obsession, where the whole world bends for a character. The result is disconnection and boredom. Characters that feel silly, dumb, unwise, ego obsessed.

Still damn good books. The fact that they discuss this aspect is fascinating. I'd much rather have this aspect of humanity expressed, no matter how difficult it is, than to pretend it is not there.

As someone else said in this thread, it is your time, and if you decide to not waste it on Murakami, that's fair. But if you ever decide to give it a second shot, I'd say don't expect any bars to be met. Just engage with it as it is.

Imagine how boring the world would be if every artist tried to conform to how you thought they should represent characters.
You're being downvoted, but you're absolutely right. Even though I personally enjoyed some of his books they'll never quite be in the same realm of those of my favourite authors because it's glaringly noticeable when characters that represent half of humanity are systematically written more poorly than the other half. It knocks the readability of a book like Hard Boiled Wonderland down from exceptionality and into the realm of guilty pleasure reading for me (and lessens my inclination to reread it).
I think I see what they are saying. Everybody has their own standards and I’m of the opinion that there are so many great books and we have so little time on this planet that if you have a problem with a book, quit it and move on to the next.

There are authors who are famous for being great at everything except endings. One of them has let me down a couple of times and I won’t start a book of theirs if reviewers say anything about a bad ending.

I like Murakami. I've read practically every word he's written. I have almost every novel he's published and look forward to new releases.

He's got some very unique ideas and I like unique.

But that dude's got some weird thing going on with women.

Murakami is just a more literary version of those boomer newspaper comics about how much they hate their wives and how all women are mysterious aliens from other planets.

(Exception for Hard-boiled Wonderland, which doesn't have enough women to be weird, and also was accidentally plagiarized or something by the nearly identical anime Haibane Renmei.)

His backstory of just deciding to open a jazz club in Tokyo as a college undergrad is… a lot more possible in Japan than the US, but is still a pretty boomer life story.

Strangely, this doesn't stop people from assuming he's going to win a Nobel someday.

I believe Michael Moorcock has an enduring discussion with women writers on this problem space, perhaps from a different perspective but I believe it forms part of their mutual discourse around the nature of feminism and pornography in new-age writing.