20. The Usual Suspects
It’s not that the movie’s all that hard to follow as it’s going, or that the now-legendary Big Twist renders the movie all that hard to resituate on repeat viewings. But if you (like your film editor) were one of those original viewers, in that summer of 1995, who saw Bryan Singer’s neo-noir mystery cold, it was awfully difficult not to feel like a schmuck afterwards — i.e., How could I have missed that? How did it not even occur to me? And we never believed anything in a movie again.
19. The Big Sleep
In all fairness to the viewer, the near-impenetrability of Howard Hawks’ 1946 adaptation of Raymond Chandler’s novel is not entirely our fault. The story goes that at one point in the shoot, director Hawks and screenwriters William Faulkner, Leigh Brackett, and Jules Furthman realized that, between all four of them, they weren’t certain about a key plot point (whether the chauffeur’s death was a murder or suicide). So they sent a wire to Chandler and asked him to clarify; the novelist replied that he wasn’t certain either. So when even the people making the movie can’t follow it, why do we beat ourselves up?
18. Tinker Tailor Soldier Spy
On the other hand, we’re pretty certain John le Carré was crystal clear about every event in his George Smiley novel, and that director Tomas Alfredson and screenwriters Bridget O’Connor and Peter Straughan worked it all in — which is a bit of a problem the first time you see it, since the labyrinthine narrative, with its many pale Europeans betraying each other, is just a tad hard to follow. It takes a couple of viewings for most audiences to fully piece together exactly who’s doing what to whom, though it must be said that there are worse ways to pass the time than revisiting this elegantly played and splendidly cast spy thriller.
This 1971 Belgian fantasy/horror movie concerns a labyrinth inside a mansion where characters from Greek mythology are trapped by a bedridden Orson Welles. So it requires not only extensive knowledge of said Greek mythology, but a head for twisty narratives and an eye for surrealistic imagery. In other words, it’s the kind of movie best consumed after one gives up figuring it out and gives in to the consumption of hallucinogens.
Nobody likes fucking with your head at the movies more than David Cronenberg, and this 1999 sci-fi mindbender (released about a month after the similarly themed but more multiplex-friendly The Matrix) takes a deep dive into video games and virtual reality, and their fuzzy overlaps with the “real world.” Between all the shifting realities and changing personalities, it gets a little complicated. Cronenberg had to acquire independent financing for this one after setting it up at MGM; the Lion ultimately passed on the project because they worried audiences would find it too hard to follow.
15. Mr. Nobody
Jaco Van Dormael’s trippy 2009 sci-fi/drama hybrid concerns the Earth’s last mortal, a 118-year-old man (Jared Leto) who spends the movie recalling the key moments of his life — which are then explored via alternate realities and many-world interpretations. It’s become something of a cult film, as “cult film” is often synonymous with “movie people keep watching again and again, trying and failing to understand.” Speaking of which…
14. The Fountain
… on the eve of Noah’s release, let us remember that Darren Aronofsky once convinced a major studio to finance a triptych story of a modern scientist, a bald space traveler from the future, and a 16th-century conquistador coming to terms with death. It’s gorgeous, and moving, and, um, challenging? Challenging is a good term to use when you’re not sure what exactly the hell’s going on in a movie, right?
Andrei Tarkovsky’s 1972 adaptation of Stansilaw Lem’s novel mates science fiction and straight-up art filmmaking, giving us a beautiful, deliberately paced (165 minutes) story of interplanetary travel and existential suffering, and confirming that there’s nothing that makes you feel quite as slight and silly as watching geniuses on a space station contemplate mortality in Russian.
12. Altered States
Another brainy sci-fi pic, in which screenwriter Paddy Chayefsky (Network) contemplates the origin of man and the existence of God, while director Ken Russell simultaneously indulges in trippy, drug-inspired experiments in bending consciousness and shifting realities.
11. The Saragossa Manuscript
This three-hour Polish epic tells multiple stories, many of them stories-within-each-other, a kind of gradually revealed nesting doll narrative of tales that eventually interact with and comment upon each other before circling back to the film’s beginning. Long thought a lost film and only available in shoddy, shortened prints, it was fully restored and released in 1999, partly thanks to years of efforts by Jerry Garcia, who said it was his favorite film. (Do with that information what you will.)
10. A Brief History of Time
Errol Morris’ engagingly egg-headed documentary is part profile of Stephen Hawking, part exploration of his ideas: the expansion of the universe, event horizons, the uncertainty principle of particles, negative energy, the “direction” of time, the relevance of God, the purpose of the universe, and the End of It All. Morris takes great pains to make his ideas understandable, via ingenious visualizations and inventive animations, and that’s part of Hawking’s M.O.: “We should all,” he says at the end of the film, “be able to take part in the discussion of why it is that we and the universe exist.” But when interviews with Hawking and his scientist friends and intercut to create a conversation/debate, it sometimes leaves the viewer with the unsettling feeling of being the slowest guest at a particularly high-minded dinner party.
9. Synecdoche, New York
As a screenwriter, Charlie Kaufman has never been shy about challenging his audience and confounding their expectations. But when the time came to make his directorial debut, he really decided to let us have it, unleashing a big, bold, weird look at what happens when a man’s life becomes his life’s work, and vice versa. Its absurdist style and overwhelming sadness alienated even the most diehard art house viewers, but it remains a profound and powerful examination of life, art, and their often unavoidable intermingling.
8. A Scanner Darkly
With 2001’s Waking Life, writer/director Richard Linklater discovered that the “interpolated rotoscoping” animation technique was just about perfect for visualizing (frequently high) intellectuals and pseudo-intellectuals discussing the meaning of life, the flexibility of reality, and other high-minded topics. Five years later, he fused that notion with a twisty sci-fi narrative by Philip K. Dick, creating an animated nightmare dreamscape that left most THC-free viewers scratching their heads.
7. Film Socialisme
Look, you could find a place on this list for damn near anything Jean-Luc Godard has made since about 1968 or so, when he all but abandoned narrative altogether to focus on the sloganeering and message-making that had been creeping into his work since the mid-‘60s. The films are refreshingly free and frequently exhilarating; it’s also often impossible to even guess at what the fuck is going on, and that goes double for this 2010 effort, a three-movement story of cruise ships, children’s tribunals, ancient Greece, war criminals, and Patti Smith.
6. Mulholland Drive
Likewise, David Lynch is a filmmaker whose dreamlike aesthetic, in-through-the-side-door storytelling, and surrealistic imagery tends to confound literal-minded viewers. It’s hard to pick his most befuddling film, and though the bizarre visual vignettes of Inland Empire and the now-he’s-just-this-completely-different-person-maybe hook of Lost Highway are close runners-up, this viewer has seldom felt as utterly bewildered by a motion picture as I did after my initial screening of Mulholland Drive. Lynch’s 2001 mindfuck was adapted from an abandoned ABC pilot, which he transformed by adding an additional, bookending layer of fever-dream fantasy. Puzzling out its meaning became something of an Internet parlor game that spring; all these years later, it remains both a fascinating puzzle and, on some level, total nonsense.
5. Last Year at Marienbad
Cinephiles have spent over 50 years working through the mysteries of Alain Resnais’ ingenious circular narrative, and not all of them took to the challenge; writers Harry Medved and Randy Dreyfuss, for example, hilariously chose it as one of the 50 worst movies of all time in the 1978 book of the same name. There’s no accounting for bad taste, but it’s awfully easy for an impatient viewer to get frustrated by the picture’s enigmatic nature and baffling narrative.
4. Upstream Color
It’s about pigs, right?
3. The Art of Vision
Many of the films on our list have flirted at the fringes of experimental filmmaking, using its style and boldness in the service of unconventional narratives, and those touches are often what confound moviegoers accustomed to more traditional moviemaking. Said viewers just don’t know what to make of experimental films (what does it all mean?), so they’d probably be wise to steer clear altogether of Stan Brakhage’s The Art of Vision, or the Dog Star Man short films (made between 1961 and 1964) that he combined, rearranged, and repurposed to create this 1965 effort. In fact, they might just wanna avoid Mr. Brakhage altogether.
2. 2001: A Space Odyssey
Stanley Kubrick’s 1968 classic is something of a gateway into movies that make you feel stupid; after all, you’ve often heard about it solely as sci-fi, and maybe even seen some seemingly straightforward clips (opening pod bay doors and the like), so you sit down to watch it, and… what’s with all the apes? And that trip-out Star Gate sequence? And the giant space baby at the end? Occasionally in this lifetime, you will meet people who claim to have understood 2001 completely the first time they saw it; extricate yourself from these people, for they are liars. Frankly, I have a hard time trusting anyone who thinks they understand it fully, no matter how many times they’ve seen it.
Shane Carruth’s brainy time-travel story (made for all of $7000) eschewed the dumbed-down requirements of a mass audience, going heavy on the jargon, focusing on the “science” half of the “science fiction” label, and cooking up a dizzyingly complex timeline that people have actually had to create charts and graphs to clarify. Most sci-fi coasts on cheap thrills and warmed-over action; Carruth went the other way, crafting the a dense, difficult narrative that rewards — and, to some degree, requires — repeat viewings from dedicated obsessives.