Most films are pretty linear and easy to follow in their storytelling. Others are muddled, but make sense when you think about them — like Memento. But some, some are designed to bewilder, obfuscate, and confuse.
These 15 films are all varying degrees of head-scratchers. Some you can pick apart with a bit of work, some you are deliberately impossible to understand, but all are worth the effort of the attempt. Oh yeah, spoilers.
Primer
Shot for a mere $7,000, Primer is about time travel. Sort of. It’s more about the breakdown between two people, but an incredibly confusing causally linked time travel mechanism underpins it. If someone tells you they understood it on their first viewing, they’re a filthy liar.
Written by a mathematician/engineer, none of the jargon or lingo is cut, making it as factually accurate as one could imagine a time travel story to be. The plot loops in on itself in recursive and terrifying ways. Trying to follow it? Good luck.
Yes, it really is that batshit confusing, but watching it over and over to pick it apart is surprisingly fun. Unlike some of the other films on this list which are confusing just to be confusing, Primer actually makes complete sense, if you’re willing to put enough time and effort into it to understand what’s going on.
Synecdoche, New York
Again we see a Charlie Kaufman flick. The guy really does excel at the mindfuck. This time starring the superb Philip Seymour Hoffman as a play director crippled by neuroses who receives an immense grant, and sets up a massive play in a warehouse where each actor acts out a private and banal life, mimicking the outside.
Slowly the play begins to mirror the outside world more and more, as he is afflicted by a mysterious illness, to the point where he hires actors to portray people outside, including himself.
The film twists in on itself constantly, with the impossibly large warehouse eventually housing a full replica of New York City, including its own impossibly large warehouse, and so on. Sharply dividing to critics, some hailed it as the best film of the decade, others as unintelligible gibberish. Thematically dense but incredible, if you can follow it, you’ll be justly rewarded.
Eraserhead
I know, we’ve already seen Lynch on this list, but could I really ignore the famously off-the-wall Eraserhead? It’s completely and utterly indescribable.
There’s a guy, his wife, a horribly deformed baby which may or may not be human, explosions, machinery, oozing wounds and liquids, eraser shavings, and more craziness than I can even understand. It was Lynch’s first feature film and is 89 minutes of pure snake-fucking crazy.
Highly influential, but still utterly unintelligible, there’s really nothing you can do but try and ride it out, or devote a lifelong academic career to trying to decipher it.
Donnie Darko
Donnie Darko is much, much deeper than I originally gave it credit for. I first went in with my brain turned off, expecting something “quirky”, but not actually deep. What I got was only the tip of the story, and it turns out there are volumes more information that you need to really appreciate what was going on — mostly given via the notoriously twisted and labyrinthine website.
Holy Mountain
Chilean filmmaker/artist Alejandro Jodorowsky is either the closest thing we have to a mad prophet, or utterly insane, and I can’t decide which. Anything he makes is so densely packed with symbolism and metaphor that it will break your brain trying to understand what everything means — and it all means something.
Steeped in tarot, mysticism, Christian magic, alchemy, and everything else weird and wonderful, his work is transcendental, if you can follow it. He’s more or less given up on film these days, instead focusing on comics where he isn’t limited by things like the laws of physics or budgets.
Unfortunately, his later work has become almost a self-cliché, invariably hitting the same points over and over. Here’s something interesting, grab anything he’s done in the last 25 years, and tick off which of the following are in it: incest, violence and mutilation between family members, castration of a son by a father, a horrible disfiguring wound caused by a parent figure, obese and corrupt priests, back-stabbing royalty. Yeah, all of his stuff hits these points, regardless if it’s fantasy, historical, or sci-fi.
Mulholland Drive
Pretty much any film by David Lynch belongs on this list but lets bundle most of them up in with Mulholland Drive, which is possibly his most acclaimed work. Let’s face it, barring maybe Elephant Man and Dune, Lynch’s work is uniquely surrealist, and hard to follow regardless of how well you understand his corpus of productions.
Lynch has specifically avoided offering explanations of the goings-on in Mulholland Drive, instead intentionally wanting viewers and critics to create their own opinions. Non-linear, bewildering, and inter-cut with seemingly unrelated chunks, it’s hard to follow even at the best of times, yet remains a powerful and influential film.
Jacob’s Ladder
Military experiments, death, drugs, and psychic powers. Jacob’s Ladder is an utterly horrifying trip into the mind of a broken individual trying to escape the legacy of the horrors of Vietnam. I won’t ruin the ending — which could be viewed either as a cop-out or else the only logical end of the story — but it’s a kick in the gut, that’s for sure.
Increasingly horrific hallucinations plague Jacob as he learns more about just what happened when he was wounded during the war, and how it’s linked to everything that’s happened since then. Uniquely terrifying and difficult to pick apart, the ending kind of does away with any real need to explain what’s going on.
Naked Lunch
Cronenberg directing a book by Burroughs. You know there’s going to be nothing but batshit crazy here. Only really tangentially related to the book, Peter Weller’s laconic take on the insanity and surreality that surrounds him rapidly becomes an anchoring point for the viewer.
Talking insects, hallucinogens, murder, sentient typewriters, psychic communications, bodysuits, and all other manners of weirdness pervade it, and it’s certainly not for the squeamish or easily bewildered. Unlike many of the other stories on this list, Naked Lunch isn’t capable of being picked apart, instead, it’s intentionally obtuse and inscrutable. Just sit back and enjoy the ride.
2001: A Space Odyssey
2001 is pretty damned hard to follow, mostly due to the bookends of the film, with the prehistoric opening and incredibly trippy closing, which serve to bewilder many viewers. The bit in the middles is just fine, though.
Kubrick was famously exacting in what he required from his films, and the slow pacing is entirely intentional, and so too is the requirement that you as a watcher actually have to think and interpret what is happening, and not have it handed to you on a platter.
The transformation into the Star-Child — and proceeding bad trip through space — is definitely obtuse and was designed to be open to interpretation. My personal view is that when Bowman activates the monolith, he’s whisked to an alien zoo for observation before they ascend him into a new form. But hey, that’s just me.
Akira
Without having read the immense manga or hitting Wikipedia, understanding Akira on the first viewing is extremely tricky. The amount of information presented to the viewer is minimal, and the whole “wait, what happened to Akira? Where did he go? And the blue kids? There’s another universe?” thing is pretty damn hard to get your head around, especially when most of the movie only explains these things tangentially, and you’re more concerned about Tetsuo’s crazy ass powers.
Repeated watching and further research really do clarify what the hell is going on because otherwise you’re left bewildered.
Adaptation
Adaptation is utterly confusing, and unlike other films that blur the lines between reality and fantasy within the world of the movie, it takes on the borders between film and real-life — as in our real life.
Adaptation is an adaptation of a novel called The Orchid Thief, which has no plot to speak of. So the movie is about the movie’s writer struggling to adapt the book and make a screenplay, which ends up being about him struggling to write a screenplay about the Orchid Thief.
It consciously slips between Kaufman’s attempts to write a script true to a book that can’t be adapted, while shamelessly throwing in Hollywood-esque features like explosions, car chases, and love stories. Yeah, it’s bewildering, and just how true any of it is entirely up for debate. It’s still a great film, though.
Solaris
Partly due to being in Russian and partly due to its legendary slow pacing, Solaris (the 1972 version) is notoriously hard to follow.
Often called the Russian 2001, Solaris takes place on a space station where the researchers are starting to hallucinate and go insane. The hallucinations cause plenty of questioning about the nature of their reality, which when combined with a psychologist main character and the question of how to approach a truly, truly alien lifeform has lead to many scratching their heads.
The final open end to the film leaves just as many questions raised as it answers. It’s still a damn good movie if you can handle the glacial pace, but don’t expect any easy answers.
eXistenZ
Cronenberg excels at making you question what is real and what is not, and eXistenZ asks that about video games and reality, as the story blurs the boundary between at least three or four levels of the interaction of both.
With the advent of a total immersion video game, eXistenZ is all about asking how much is free will, how much is scripted, and how much is even real. As multiple levels of games and reality begin to emerge, the final scene eventually feels like the whole movie has been sorted out — until the very last line.
Pi
Darren Aaranofsky’s first major flick was Pi, and this twisted black and white look at obsession and paranoia was enough to get him into the big leagues.
It’s a combination of Aaranofsky’s trademark incredibly quick cuts, the dense subject matter, and an unreliable narrator that causes Pi to be tricky to follow, as Max Cohen struggles to understand the universal patterns that occur through nature as a way of understanding and predicting the stock market.
As he uncovers more and more of a number that may be at the root of things or may be the unknown name of God, his sanity begins to erode, and his headaches increase, his final inevitable decline is as horrific as it is a relief — both for the viewer and the character.
Vanilla Sky
While personally I didn’t find this American remake of the Spanish psycho-thriller that bewildering, there were plenty who did, to the point where it was voted the most confusing film ever by a DVD rental company.
The fact of the matter is that much of the perceived twistedness and confusion from the plot is all resolved by the classic cop out “it was all a dream.” While perhaps not as utterly blatant as that, but the entire film takes place in the lucid dream of a man in cryogenic suspensions whose subconscious has started to assert itself. That explains the constantly switching nature of reality and the weirdness that surrounds him. There, easy.