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[Flying Dice]

My track record might suggest otherwise, but I've had to sit through several years of derision about Lost having never watched it. So, I dunno, I might be a little too prejudiced.

The Prisoner, yeah, have had that suggested before. I should probably watch the originals.

I'm seconding Vector on this one. The original The Prisoner was excellent.

[itisnotlogical]

Is Event Horizon really all that weird/esoteric? I always thought it was just a regular horror movie.

The Holy Mountain by Alejandro Jodorovsky is great. Incredibly surreal. The "story" is about a Christ allegory wandering through a post-apocalypic (?) landscape and all the characters he meets along the way. Your viewing would probably benefit from a bit of basic religious knowledge, like all the famous Christian stories and such. Either way it's pretty trippy.

If you like/don't mind anime, there's Neon Genesis Evangelion. It only really hits it's "mystical sci-fi drama" stride toward the end of the series, but it's really best taken as a whole. The movie End of Evangelion is required viewing for animation fans anyway IMHO.

And popular or not, Game of Thrones can have some creepy moments. Not so much scary, just incredibly messed-up and weird. Those mostly come later in the show though, towards season 2 and 3.

[nenjin]

You're questioning Event Horizon's esoteric creepiness, but then go on to suggest Game of Thrones? (I already watch it.) It's moments of the weird are pretty straightforward fantasy, in my mind.

Event Horizon is, for the most part, a horror movie. But somewhere around 60% through it becomes something a little more. It doesn't have the symbolism, but it leaves you with questions none the less, about what's really out there, what we actually know, ect...but yes, it's probably one of the most straightforward ones on that list. But it's kind of right there with Lord of Illusions, where's about horror, but underpinning that horror is an element of magic, of the unknown.

Anyways, watching Lucifer Rising I realize a friend (who also digs the occult) showed me it already. But it was at work, which isn't the best time to watch these sorts of things.

[bucket]

Mindfuck shows, eh? I've heard good things about Hemlock Grove, but it's a Netflix exclusive.

The Frighteners is a Peter Jackson film that starts off campy... but halfway through it gets REALLY fucking dark.

The Prestige is an interesting movie with a crazy twist at the end. Lots of good acting in that movie, and of course it's directed by Christopher Nolan.

I was pleasantly surprised by Cabin In The Woods, which turns the horror genre on its ear. A lot of people complained about the ending, but I think they expected a different movie altogether.

The Cell is an excellent mindfuck movie with delicious visuals. Yeah, it's got Jennifer Lopez in it, but just block that part out and watch it.

The Thirteenth Floor is a movie that came out around the same time as The Matrix, and had a lot of the same themes. This was decidedly more cerebral. Dark City is another movie from that time period, again with the same kind of theme, but much weirder.

Cube is an unconventional horror movie with an insane premise that you'll most likely lose sleep over. There are two sequels that expand on it (but the acting is subpar).

Arlington Road is an interesting twist on the political thriller genre. It's not at all predictable.

There's no shortage of anthology series with dark themes. The Twilight Zone, The Outer Limits, Tales From The Crypt, Freddy's Nightmares, Are You Afraid Of The Dark?, Tales From The Darkside, Alfred Hitchcock Presents. Those are all great.

Speaking of which, the classic Tales From The Crypt movie is extremely twisted.

I recommend Stephen King movies. The acting can get kitschy at times, and most of his movies are horribly dated - but if you can look past that, there's a lot of incredible stuff out there. He's not typical slasher horror, but the good stuff that'll keep you up at night.
The Stand
The Mist
Creepshow
It
Salem's Lot
The Dead Zone
Nightmares & Dreamscapes

I'll stop before I end up writing a novel.

[nenjin]

The Cell is an excellent mindfuck movie with delicious visuals. Yeah, it's got Jennifer Lopez in it, but just block that part out and watch it.

I really enjoyed this movie. It's just a shame it was a major Hollywood release, because I felt like the story could have been more interesting but it essentially is reduced down to basic plot movements so people don't get lost, and a lot of delicious imagery. If The Cell had been made by like, David Lynch, it would probably be in the top of my esoteric movies. As it is, it falls somewhere between great weird movies....and your garden variety horror/dark/occult movies.

I'm well-versed in Stephen King movies. Still haven't watched the Stand, that's one I keep meaning to check out but never have the time for.

[Il Palazzo]

The Cell is an excellent mindfuck movie with delicious visuals. Yeah, it's got Jennifer Lopez in it, but just block that part out and watch it.

I really enjoyed this movie. It's just a shame it was a major Hollywood release, because I felt like the story could have been more interesting but it essentially is reduced down to basic plot movements so people don't get lost, and a lot of delicious imagery. If The Cell had been made by like, David Lynch, it would probably be in the top of my esoteric movies. As it is, it falls somewhere between great weird movies....and your garden variety horror/dark/occult movies.

Have you seen The Fall by the same director(i.e., Tarsem Singh)? It's got the same grade of luscious, awe-inspiring imagery employed, but in the service of a very modest(but not simple!), heartfelt and bittersweet plot. It's not really a serious head-scratcher, but it's different than most. One of my all-time favourites.

[nenjin]

Never heard of it, but I'll add it. Cause 'dem visuals.

[Reelya]

How about Pan's Labyrinth. Idk if it's quite like what you listed, but it's really good.

If you don't mind animated, stuff by Japanese director Satoshi Kon (who sadly died young) is all a mindtrip, and very good (mostly movies, but one show, Paranoia Agent), his stuff often blurs the line between fantasy and reality (Pan's Labyrinth does too).

And a little lesser known, but talented director Yuasa Masaaki, he's like Satoshi Kon took too much strong acid, mostly does TV, but he worked on the films Cat Soup and Mind Game. Recommended shows: Kaiba, Tatami Galaxy and Kemonozume, they're all around the 11-13 episode length, so not long series. His art style takes a lot of getting used to though, looks nothing like anything else coming out of Japan.

[nenjin]

Pan's Labyrinth is close, I debated adding it to the list a couple times but didn't. It's Dark Fantasy, and it can certainly be weird, but I don't know if it's esoteric enough. Then again, I counted Event Horizon, so maybe it is.

I've seen a bit of Paranoia Agent and I enjoyed it, but some of the SFX they used really started to get on my fucking nerves. The whole NEENER NEENER NEENER NEENER crazy-sound that plays frequently finally bugged me too much.

As an aside I'm using Netflix streaming for the first time and NONE OF THESE GODDAMN MOVIES ARE AVAILABLE TO STREAM.

That said, Hemlock Grove looks intriguing.

[Delta Foxtrot]

Came to mention Riget, saw it done already. Bummer. Also seconding Dark City.

How about Tideland and to a lesser extent some of the other things Terry Gilliam has done? His production in general is probably "too normal" for the purposes of the thread. Worth mentioning though.
Tideland doesn't have the horror/action aspect that oozed to me from your OP list, but I'd argue it's quite strongly a "weird, esoteric movie". The few people I've shown it had brain broke and lost their faith in humanity for a while. Personally I'd draw some parallels between Tideland and Pan's Labyrinth. So maybe, maybe.
Basically it's a film with the perspective of a child, amidst gross parental negligence and abandonment. Imagine horrible things happening, now present them in a playful manner. That's basically Tideland. And by horrifying I mean that the concepts are horrifying. There's no gore that I can remember in the film. And there's Jeff Bridges, he's always nice.

[itisnotlogical]

Oh! Again, if you don't mind anime, there's the original Ghost in the Shell movies, which are very heavy on the symbolism and existential themes. They're both beautifully animated anyway, which should be reason enough to watch them. I can take or leave the ones based on Stand Alone Complex, to be honest.

[Reelya]

Yet again for anime - Kuuchuu Buranko (aka Trapeze). It's one of the most esoteric cartoons I've ever seen. Weird visuals, weird story.

Seconding Terry Gilliam, especially "Brazil".

[Il Palazzo]

I think we've collectivelly forgotten to mention Memento.
It's a film that goes backwards.

[RedWick]

I'll recommend Dark City.  It's an oddball sci-fi flick that definitely falls into that esoteric cateory.

And I'll third anything by Terry Gilliam.  Time Bandits, Brazil, Twelve Monkeys, The Adventures of Baron Von Munchhausen...

[nenjin]

Seen Memento. It's definitely weird and mind-fuck-y.....but there's no sense of the mystic. Which isn't a requirement but it definitely helps.

Also seen Brazil. Terry Gilliam, you weird wonderful bastard.