20 Mindbending Movies That’ll Have You Scratching Your Head For Weeks

All art forms are capable of messing with our minds: take M.C. Escher’s paintings, for example, or even the novels of Bret Easton Ellis. And cinema is no exception, with some of the greatest filmmakers exploiting its capabilities to create some of the most mind-bending movies of all time. Here, for example, are 20 ingenious flicks that defy easy explanation and could take weeks of chin-scratching and contemplation to fully appreciate – if they don’t melt your brains down into mulch, that is…

20. Under the Skin (2013)

Scarlett Johansson is a predatory alien in 2013’s Under the Skin, a dark, brooding and thought-provoking sci-fi flick set in Scotland. And it’s likely to actually get under your skin, too, thanks to its doomy soundtrack and some surreal and disturbing imagery. The purpose and motives of Johansson’s unnamed protagonist, meanwhile, are never made entirely clear, and the question as to whether she ever gains a shred of humanity in the process could almost fill a whole Ph.D. thesis.

19. 2001: A Space Odyssey (1968)

2001: A Space Odyssey begins with cavemen discovering a blank, black monolith – a puzzle that neatly sets up Stanley Kubrick’s visually and conceptually breathtaking masterpiece as a film that will leave the viewer with a lot to think about. Within its nearly two and a half hour running time, then, the whole story of human existence is thrown into question – and that’s not even to consider the nature of HAL’s consciousness…. The scope of this 1968 classic is both stunning and terrifying. It’ll leave an imprint on your mind forever.

ADVERTISEMENT

18. Donnie Darko (2001)

At a time when others were swooning over Tara Reid in American Pie 2, Donnie Darko was the introverted, thinking young person’s high-school movie of choice. Richard Kelly’s dark drama follows Jake Gyllenhaal’s eponymous outcast as he is haunted by an anthropomorphic rabbit, not long after a rogue plane jet engine unexplainably falls from the sky onto his bedroom. Oh, and all that while trying to deal with an impending apocalypse. It’s just as weird as it sounds…

17. Mulholland Drive (2001)

ADVERTISEMENT

What’s the meaning of the blue box? Why did that horrible man-monster jump out and scare Patrick Fischler’s character at the diner? Are all these people even separate entities or just projections of a troubled mind? These are just some of the many questions that Mulholland Drive, David Lynch’s surreal stab at Hollywood noir, brings up – and to this day the internet is still scrambling for definitive answers.

16. Inception (2010)

This dream-based thriller about a crack squad of manipulators who attempt to plant thoughts in a man’s subconscious by entering his dreams is wrapped in so many layers of rules about how dreams work that you inevitably lose track of which layer the action is happening in. But then that’s presumably director Christopher Nolan’s goal. Needless to say that upon watching Inception, your head will probably be whirling at about the same rate as the film’s fabled spinning top.

ADVERTISEMENT

15. The Matrix (1999)

ADVERTISEMENT

It may seem unoriginal now, even clichéd, but the idea that our entire reality is a digital illusion blew away the theater-going masses when The Matrix debuted on screens in 1999. We can forget about the sequels, but we should never forget about the ingenuity of the original Matrix movie, which blended mind-blowing action with a profound plot that had a whole generation questioning the very nature of life, the universe and everything.

14. Inland Empire (2006)

David Lynch’s 2006 follow-up to Mulholland Drive makes that movie look practically conventional by comparison. Indeed, Inland Empire completely ignores the laws of time and continuity as an actress attempts to immerse herself in the role of an apparently cursed movie. And it’ll get the viewer asking what’s real, what’s not real and what exactly the deal is with those terrifying rabbit people talking nonsense to the sound of canned laughter.

ADVERTISEMENT

13. Being John Malkovich (1999)

ADVERTISEMENT

Being John Malkovich is wackier than its name might suggest, seeing as it’s about a couple who discover a hole in a wall that allows them to spend 15 minutes in the head of the veteran actor and director. Why did no one think of this before? Because it’s the kind of ingenious madness that only screenwriter Charlie Kaufman can come up with. It also answers the somewhat inevitable question: what happens if John Malkovich enters the head of John Malkovich? Well, let’s just say that one word can mean anything…

12. Synecdoche, New York (2008)

If you somehow managed to wrap your head around Being John Malkovich, then you’re ready to upgrade to Charlie Kaufman’s first stab at directing. Synecdoche, New York follows theater director Caden Cotard, a man who wants to create one final masterpiece involving many people living unreal existences in a warehouse located in a mock version of Manhattan. And as if that wasn’t confusing enough, along the way Cotard gets so immersed in the creative process that both play and reality fuse into a hazy, visually stunning mess.

ADVERTISEMENT

11. Videodrome (1983)

ADVERTISEMENT

Few directors manage to produce a fare both mind-bending and stomach-churning in equal measure as master of body horror David Cronenberg. And his 1983 chiller Videodrome, about a TV executive who becomes obsessed with an illicit TV show that broadcasts snuff movies, manages to simultaneously be a deft satire of the salacious nature of the media and a movie in which James Woods shoves a handgun into a giant vagina-like orifice that opens up on his stomach. Yes, really.

10. The Fountain (2006)

Darren Aronofsky’s spectacular 2006 drama The Fountain follows three couples, living eras apart, all of whom are played by Hugh Jackman and Rachel Weisz. And, at one point, for whatever reason, a tree, too… The three somber stories, though, are closely connected, all focusing on the theme of death and how to deal with it. And while it may be a bit overblown, it’s nevertheless a multisensory trip that will leave you musing.

ADVERTISEMENT

9. Eternal Sunshine of the Spotless Mind (2004)

ADVERTISEMENT

When a former couple find a way to erase all memories of their relationship, things get baffling when one of them changes his mind. He begins hiding his recollections to stop them being erased, at which point Eternal Sunshine of the Spotless Mind begins to spiral into a mind-bending meditation on the nature of life, love, loss and, indeed, the ethics of cleaning out bad memories. Still, it’s perhaps not one to watch after a bad break-up…

8. Memento (2000)

It turns out that alternating a movie between color and monochrome shots – with the former in a reverse chronological format and the black-and-white sequences in normal order – is a great way to capture the confusion and paranoia felt by an amnesiac man whose life is in perpetual danger. Naturally, all that makes Memento a total head-scratcher – but then you wouldn’t expect any less from mind-game king Christopher Nolan.

ADVERTISEMENT

7. 12 Monkeys (1995)

ADVERTISEMENT

In 1995’s 12 Monkeys a prisoner with nothing to lose is trained, and subsequently travels through time, to stop the outbreak of a virus that wipes out nearly all humanity. Things go somewhat awry, though, when he’s sent to the wrong time and ends up in a psychiatric hospital. And despite escaping and managing to convince a respected scientist that he’s speaking the truth, he soon starts to believe that he is indeed crazy. Typically maddening fare from Terry Gilliam – but then would anyone think that a former member of the Monty Python team could produce anything conventional?

6. Vanilla Sky (2001)

Things start off simple enough in Vanilla Sky, the 2001 Hollywood remake of Spanish headscratcher Open Your Eyes. A handsome man, played by Tom Cruise, falls in love with a beautiful woman, portrayed by Penelope Cruz, and the stage seems to be set for a – albeit somewhat offbeat – rom-com. But when Cruise’s character’s face is disfigured in a car accident caused by a possessive ex, the film enters several stages of weird meta, descending into a maze of lucid dreams, subconscious madness and cryogenic freezing.

ADVERTISEMENT

5. Enter the Void (2009)

ADVERTISEMENT

A movie about a deceased drug dealer whose soul hovers over the seediest parts of a neon-lit Tokyo requires some suspension of disbelief due to its very premise – but things become even more mind-bogglingly existential when you contemplate the Tibetan Book of the Dead-linked theme threaded throughout its nearly two and a half hour running time. Regardless, even if you struggle to keep track of the dreamlike, dark events unfolding in Enter the Void, it’s still an experience that’ll make you want to take some meditative time out in a dark room for a few hours afterwards.

4. Moon (2009)

What is it about the idea of lonely men in space that makes for such clever movies? And Duncan Jones’ full-length directorial debut Moon is clearly no exception, dealing as it does with a lone astronaut working on a moon base who, upon making an unexpected discovery, begins to suspect that he may not be who – or, indeed, what – he thinks he is. What results is a stark but poignant look at a man quite literally stuck in his own company, doing his best to cope with the, well, eye-opening state of affairs in which he finds himself.

ADVERTISEMENT

3. Jacob’s Ladder (1990)

ADVERTISEMENT

On the surface, Adrian Lyne-directed 1990 horror Jacob’s Ladder concerns a postal worker dealing with PTSD following his experiences serving in the Vietnam War. But that’s far from all there is to it. Because as Jacob Singer discovers that his fellow Vietnam vets have had similar hellish hallucinations, he begins to suspect that the U.S. army had a part to play in their mental states. Amidst horrifying visions, then, he begins to question whether reality is actually in New York or still in Vietnam – and the ride is no less terrifying or thought-provoking for the viewer, either.

2. Primer (2004)

Time travel can be presented as a pretty simple thing in movies – just hop into a DeLorean, get it to 88 mph and you’re off! Not so much in Primer, though: Shane Carruth’s indie flick about a couple of rookie scientists who stumble upon the secret of time travel delves a whole lot deeper, baffling us with the fallout as we lose track of which character’s which, what time period we’re in and whether the original characters even still exist.

ADVERTISEMENT

1. Solaris (1972)

ADVERTISEMENT

Andrei Tarkovsky’s sci-fi classic Solaris fuses the vast cosmos with the darkest depths of the subconscious as a man on an eerie space mission becomes beset by visions of his dead wife, who he believes may be real. And watching it all pan out is a bit like reading an old Renaissance poem – even if you don’t “get” every single bit of it, you’ll still be enthralled.

ADVERTISEMENT
ADVERTISEMENT