Annihilation staring Natalie Portman. The wife and I went and saw it in theaters. A few people straight up walked out after a while and I heard an audible "what the fuck?" After the movie was over from someone in the theater.
On a rewatch after reading that the movie was about cancer I appreciated it a lot more, but it's a weird one for sure.
Primer. I needed to re-watch it at least 3 times to even begin understanding WTF was happening. Even the wiki sites that try to explain it are incomprehensible at first.
Zardoz. The gaint floating head with the crazy man inside shouting "the gun is good, the penis is bad," Sean Connery in a WAY too revealing outfit, the bizarre, apathetic, immortal poeple, and wierd pyramid magic.
It was hands down the most strange, unfathomable film I've ever seen, and I've watched The Dancing Outlaw.
I remember once when I was a teenager turning on the TV at like 2 in the morning on a Saturday and being treated to Adult Swim's Sealab 2021 for the first time. Along with the rest of their line up around 1999-2003. It was fucking weird as shit. But hilarious.
I recently watched Pee-wee's Big Adventure for the first time since God knows how long and it feels like a little bit of a drug trip at times with the sometimes sporadic pacing and just how it is as a movie.
EXistenZ - The final question "Are we still in the game?" really summarized the first watch experience. You have no clue what's going on anymore by that point.
Same goes for Total Recall by the way - that movie also has you guessing what's real and what isn't throughout 90% of the runtime.
The Room (2003) is without exaggeration the worst movie ever made. It's so bad that you can't even enjoy it ironically. Someone else made a much better movie (The Disaster Artist) about how The Room ever got made in the first place. Because that will be the first question on your mind after watching it.
"Under The Skin" with Scarlet Johansson. It has easily the most low-key terrifying scene I've ever seen in a movie (the beach scene). And the whole film is the very definition of wtf.
Beau is Afraid is absolutely mental. I had no idea what to expect when we went to see it, and I’m so thankful the cinema was empty so we could audibly talk about wtf was going on throughout. It’s definitely a movie I want people to watch but with the caveat that I’m not recommending it.
The Who's Tommy Pinball Wizard. I was expecting some cool music, and pinball. Maybe something like The Wall. Nope, What I got was Uncle Eddy and the Acid Queen.
Watched it because I'm a fan of doomsday scenarios. The former president of the United states starts spontaneously growing a vagina and uterus because 'life uuuh, finds a way'.
I won't wreck the rest of the plot but this movie took a fucking wild turn and left me sitting there the whole time going WTF!
I can’t remember the title but it was on uk Netflix for a while last year. It was a Spanish film where a girl had an ass for a face. That was weird in and of itself but then it just kept getting weirder the whole way through.
Mother. It's not that I didn't get the allegory, it was just weird. Also Antichrist, though to be fair, saying "wtf did I just watch" was the whole point of the movie.
Titane.
If I had been told beforehand that a woman being fucked by a car would be the least messed up part of the movie, I'm not sure I'd have believed it; however, that movie has burned it's way into my head like few others have.
You've heard of A movies. You've heard of B movies. But have you ever heard of Z movies? No? Then Thankskilling is for you! (watch at your own risk, I am not liable for the mental, emotional, and other damage that will occur).
The Northman. At no point did I know where that film was going, and when it was done I just sat in my theater seat for a second bewildered at what I had just sat through.
Specific episode of a show: Mad Men's sixth season episode "The Crash." Just a slowly unfolding trip that takes all the surreal elements of the show so much further than they had gone before or since.