10. Donnie Darko (2001)
“28 days, 6 hours, 42 minutes, 12 seconds. That is when the world will end.” Not the words of Nostradamus, but rather of Frank, the disconcerting bunny-costumed devil on Jake Gyllenhaal’s shoulder in Richard Kelly’s 2001 masterpiece of weirdness, Donnie Darko. Gyllenhaal plays the eponymous Donnie, who begins to see visions of Frank and to act on his vandalistic recommendations. And when Frank raises the topic of time travel, things take a further turn for the surreal as Donnie begins to see fluid tunnels of light emanating from other characters, showing where they will go next. With the end of the world rapidly approaching, Donnie races to make sense of these events even as the movie’s convoluted plotlines converge in a remarkably neat resolution – albeit one that nonetheless leaves viewers wondering what exactly just happened.
9. Memento (2000)
Based on a short story written by his brother, Jonathan, Memento brought director Christopher Nolan to widespread acclaim upon the movie’s release in 2000 – and for good reason. The non-linear thriller pushes the whodunit into unfamiliar territory as amnesiac protagonist Leonard Shelby, played by Guy Pearce, searches for the man responsible for killing his wife, which is one of the only things he can recall. Unable to create new memories, Shelby chooses instead to tattoo salient clues as to the identity of the mysterious “John G.” onto his body – but the fallibility of his memory proves to be a far more central problem than is first apparent. Shot in just 25 days, Memento has subsequently found its way onto countless best-film lists, and it offers valuable “how not to” advice for tattoo enthusiasts everywhere.
8. Looper (2012)
Thanks to time travel, organised crime syndicates in 2074 no longer have to do their own dirty work – according to Rian Johnson’s 2012 sci-fi thriller Looper, at least. Rather than offing their foes the old-fashioned way, future mobsters simply strap bars of silver to their victims’ upper bodies and send them back in time to 2044 – the year in which the movie is set – whereupon they are blown into oblivion by “loopers” such as Joe, portrayed by Joseph Gordon-Levitt. However, one of the perils of being a looper is that, should your employer decide to “close the loop,” you could suddenly find your future self in the sights of your own shotgun. And of course that’s precisely the fate that befalls Joe when “old Joe,” played by Bruce Willis, comes back from the future, intent on rewriting the course of his own history and triggering an alternate reality chain in the process.
7. Inception (2010)
No stranger to weirdness, Christopher Nolan upped the ante – or perhaps, more accurately, the budget – on 2000’s Memento with 2010 blockbuster Inception. We’ve all had crazy dreams before, but for spy Dominick Cobb, portrayed by Leonardo DiCaprio, dreams become the perfect playground for him and his accomplices to use to carry out increasingly elaborate acts of espionage. It’s when the crew is tasked with planting an idea – rather than stealing one – that the disorienting dream-within-a-dream-within-a-dream fun really begins. Nolan’s tastefully ambiguous ending ensures that the question of whether or not DiCaprio’s character is still dreaming goes pleasingly unanswered.
6. Love (2011)
Weaving together storylines set in the American Civil War in 1864 and aboard the International Space Station in 2039, Love marks an impressively perplexing debut from director William Eubank. The 2011 sci-fi drama stars Gunner Wright as astronaut Lee Miller and focuses on his descent into isolation-induced confusion and despair when the space station of which he is the sole occupant has its contact with Earth cut off. While on board, Miller finds the 1864 diary of Union soldier Captain Lee Briggs (played by Bradley Horne) and begins to read about a mysterious object discovered by him. What’s more, it soon transpires that the diary isn’t the only thing the two men have in common.
5. Shutter Island (2010)
Leonardo DiCaprio makes a second appearance on our list in Martin Scorsese’s 2010 psychological thriller Shutter Island. DiCaprio stars as U.S. Marshal Teddy Daniels, who is looking into the mysterious vanishing of a patient at an institution for the criminally insane on Boston Harbor’s Shutter Island. All is most certainly not what it seems, however, and the fabric of Daniels’ reality begins to unravel as a series of increasingly disorienting events develop. Is he experiencing the effects of psychotropic medicine administered by doctors at the hospital, or is something altogether more sinister afoot? As one of the nurses confides to Daniels, though, “This is a mental institution, Marshal. For the criminally insane. Usual isn’t a big part of our day.”
4. Southland Tales (2006)
In 2006 Director Richard Kelly followed up 2001 indie classic Donnie Darko with the much less well-received – and even more confusing – Southland Tales. The movie stars Dwayne “The Rock” Johnson as amnesiac actor Boxer Santaros, Seann William Scott as identical twins Ronald and Roland Taverner, and Sarah Michelle Gellar as porn star Krysta Now. A World War III-beset America provides the backdrop to a series of convoluted intertwining plot lines involving political conspiracies, limitless alternative energy and Big Brother-esque surveillance. Throw in increasingly catastrophic tears in the space-time continuum – and a floating ice cream van – and you’ve barely scratched the surface of this baffling, yet strangely beautiful, piece of cinema. Oh, were you hoping for a bit of Stifler-esque gross-out comedy? Sorry to disappoint.
3. 2001: A Space Odyssey (1968)
Epic sci-fi drama 2001: A Space Odyssey divided critics upon its release in 1968, but it has since gone on to be widely regarded as one of the great works of cinema. Directed by Stanley Kubrick and inspired in part by Arthur C. Clarke’s short story “The Sentinel,” 2001 is split into four main parts that detail interactions between people and black monolithic objects of apparently alien origin. Keir Dullea stars as Dr. David Bowman, a scientist on a mission to Jupiter in a spaceship largely controlled by the computer HAL (voiced by Douglas Rain), which claims to be “foolproof and incapable of error.” Needless to say, HAL is anything but, and Bowman soon finds himself in a battle for survival with the murderous machine. Whereas some films opt for exposition in their closing chapters, 2001 journeys in quite the opposite direction, with Bowman undergoing the kind of experience normally reserved for those who have recently ingested very strong hallucinogens. Well, it was released in the ‘60s.
2. Primer (2004)
Shot on just $7,000, but with a level of mind-bending complexity that puts many other films to shame, 2004’s Primer showed the world how you do high concept on a low budget. Written and directed by Shane Carruth, the movie follows engineers Aaron (played by Carruth himself) and Abe (played by David Sullivan) as they work on a tech project that starts to exhibit signs of the capacity to facilitate time travel. It’s not long before the duo have built machines big enough to accommodate themselves, and they start to travel back in time to earn big bucks on the stock market. All that may seem straightforward enough, but it is in fact only the tip of a dense, convoluted time travel iceberg. As Esquire’s Mike D’Angelo commented, “Anybody who claims he fully understands what’s going on in Primer after seeing it just once is either a savant or a liar.”
1. Revolver (2005)
Guy Ritchie and Jason Statham may not be the first names that spring to your lips on the topic of cerebrally challenging filmmaking, but 2005’s Revolver is undoubtedly one of the more incomprehensible movies you’re ever likely to see. Statham stars as con artist Jake Green, who has been released from prison after serving seven years in solitary and is now out for vengeance against casino boss Dorothy Macha (played by Ray Liotta). Nothing out of the ordinary thus far. But who are the mystifying but benevolent Zach and Avi (played by Vincent Pastore and André Benjamin, respectively), and who is Jake’s nemesis, the infamous “Sam Gold?” Unfortunately for audiences and critics alike, the answers to many of these questions have their roots in Ritchie’s Madonna-influenced dabblings with Kabbalah at the time – and for Jake they take the form of a very severe case of “it’s-in-your-head-itis.”