Asklemmy

Everything Everywhere All At Once.

It's just... really good.

The Big Lebowski. I've never seen another movie gain so much value over time and rewatches

Primer

Akira. It's weird and confusing. Goes from cyberpunk eye candy to bizarre metaphysical reality warp real quick.

Shutter island watches completely differently on the second watch, same with Primer, The usual suspects, and Moon (2009).

2001: A Space Odyssey

It's my favorite because of the cinematography and atmosphere. It's my favorite because of the themes and philosophy. It's my favorite because space and psychedelia are cool.

It's just an all around great movie if you can appreciate the slow pacing and intentionally jarring or tense aspects that drag on. 30 minutes of monkeys fucking around for seemingly no reason (at least, at first). Discordant wailing that lasts so long it nearly leaves your ears ringing. Space shots with no sound at all, or just the hissing of the space suit, which linger on the slow drift of a character moving from one location to the next. A character begging for his life as another dismantles his brain bit-by-bit.

To me, this movie always flys by, and it always feels like i was there in it, fully immersed. To my friends, it lasts a week and has one cool part that took an eon to get to.

Also it begs for multiple watchings to develop a theory of what the fuck is happening at the end and what the obelisk is and where it comes from.

It also raises philosophical questions that are interesting to come up with and grapple with in new ways with each viewing. Is HAL alive? Whats the next leap in evolution? can uncomfortable art be good? Who owns the moon? How did consciousness evolve? What's happening to Dave?

Hot fuzz. Because the first watch is enjoyable, but every subsequent rewatch makes you appreciate Edgar Wright more and more. He is just the most incredibly meticulous story teller with the most dense movies.

Donnie Darko. Besides being confusing, it’s just a great story. Plus, it’s remarkably well cast.

If you have the opportunity to watch the deleted scenes, I highly recommend it - especially the one with the dad. His role in the cinematic version is pretty small, but there’s a deleted scene where he has a quiet chat with Donnie, and tells Donnie about his past mental problems. It’s fantastic, and rounds out his character perfectly.

Memento.

Though, being real, I would say that it's a movie that gets more interesting on second watch rather than being one out need to watch twice to get. I honestly haven't ever run across a movie like that.

Primer because you don't know what's happening at the start, and then you start to piece it together, but you really have to watch it a few times because the details you pick up provide context for what's happening allowing you to piece more of the puzzle together.

The Big Lebowski. You pick up on stuff with each watch, and it just gets funnier when you do.

I want to put in my ticket for What Dreams May Come, one of Robin Williams more heartfelt and serious roles, and one rarely mentioned. You can "get" the movie on the first watch and only really begin to understand all the nuance and subtlety during the second or third run.

Snatch.

There's like 15 main characters. Every scene is important but it is impossible for it all to be apparent on a first watch.

It's really brilliant storytelling. Watching Lock To k & Two Smoking barrels, you realize that guy Ritchie might be a one trick pony. But that's okay, it's a great trick.

"Dude Where's My Car?" It has a truly in depth and beautiful meaning to it that only becomes obvious on a third viewing.

I'd go with Possessor by Brandon Cronenberg. I've only seen it once so far, and the unfolding of the story was such that you had to work for it. It wasn't impenetrably dense, but I definitely had to give it the attention it demanded.

I like primer, but I'm not sure I really understand it even with all the charts and diagrams that are out there

not so much for understanding but, fight club is a different movie the second time around.

American Psycho for me. I had a lot of questions after watching it for the first time. It doesn't have what I'd call a "satisfying" conclusion, but that's what makes the movie what it is. It's kind of a mindfuck, and the subtle humour in it is just top notch.

The Holy Mountain. I suggest just watching it.

The matrix and Fight club ( both released in 1999 )

The Prestige.

Okay this isnt a movie but a show, but arrested development (especially the early seasons) are filled with situations, puns, innuendos and jokes that are set up over several episodes, sometimes even seasons. It is impossible to catch and appreciate them all on first watch. I have seen the show probably a half dozen times over the years and i still stumble over the occasional thing i missed.