Gus Van Sant was one of the most important directors of the "New Queer Cinema" movement, and one of his most challenging and confusing movies is Elephant. Released in 2003, its focus on a school shooting and those involved in it, including the perpetrators, was controversial, given the recent school shootings that had occurred. It also withholds easy answers, and its elliptical and meandering narrative can make it sometimes difficult to follow, particularly for those who aren't well-versed in the director's use of cinematic techniques and narrative. For all of that, it remains a powerful piece of filmmaking.

Caligula, as one might expect from the title, focuses on the turbulent reign of one of ancient Rome’s most infamous emperors, portrayed here by Malcolm McDowell. This film works overtime to thwart the viewer’s expectations of what a biblical epic should look like, and it works overtime to be as sexual, naughty, and provocative as possible. The end result can be a bit of a confusing mess, particularly since it went through several versions and endured a great deal of cutting and censorship. Fortunately, there are some signs that a reconstructed edition might be able to provide viewers with the intended version of this remarkable film.

Oliver Stone has repeatedly shown an interest in important historical subjects and personages. In Alexander,  he sought to explore the complex psychology of Alexander the Great (played here by Colin Farrell). The film offers a complex portrait of one of history’s most complicated figures, but its fragmented narrative, which frequently shuttles between different periods in the conqueror’s life, ultimately becomes distracting and disorienting. Making matters worse is that the film was re-released in several editions, each subtly different from the rest. Alexander becomes a testament to a director who isn’t quite sure what film he’s trying to create. 

The Wachowskis have undeniably impacted Hollywood filmmaking, and in some ways, The Matrix  remains their magnum opus. In part, this stems from the performance of Keanu Reeves, who captures so much of what makes reluctant hero Neo Anderson. In this case, the confusion stems not so much from the film’s story, which is very much cut in the hero’s journey mold, but instead from the weighty nature of the themes that it addresses, many of which revolve around the vexed question of human consciousness and just how much modern human subjectivity. 

Tim Burton’s remake of Planet of the Apes is one of those films that should work, at least on paper. After all, the director had already established himself as one of Hollywood’s most unique voices, and Planet of the Apes was an enduringly popular piece of sci-fi filmmaking. Some pieces of the film work, but others are confusing, and though both plot twists try to recapture some of the shock of the original, neither land with quite as much impact. The final moments of the film, which see the main character Leo managing to make it back to Earth only to find out that Thade had somehow made it there before him and remade the world in his own image, is so ridiculous that it essentially torpedoes whatever goodwill the film had managed to accrue up to that point. In the end, it ends up being confusing in a way that is frustrating rather than rewarding.

Few films have captured millennium angst and teenage despair quite like Donnie Darko.  It features one of actor Jake Gyllenhaal’s most memorable performances. He plays the title character, a young man tormented with visions of a demonic rabbit who tells him when the world will end. While it is certainly a thought-provoking film and one that neatly captures the sense of angst and doom that lingered around the turn of the millennium, it’s also one that raises more questions than it’s willing or able to answer. Perhaps, though, the film’s sense of narrative confusion is key to its enduring appeal among Gen Xers and older millennials. 

Gregg Araki excels at using films to push at the boundaries of the kinds of stories that films can tell. It's thus no wonder that he is also widely seen as one of the foremost artists behind the movement known as "New Queer Cinema," which emerged in the 1990s. Nowhere is one of his more challenging films, with a plot that draws in adolescent desire, Gen X angst, and even aliens. Then again, the whole point of the film seems to be to create confusion to more accurately and aptly capture the troubled mindset of its teen characters. Araki's films are reminders of how exciting cinema was in the 1990s.

Fight Club, like many other films that emerged at the end of the 20th century, captured so much of what made that period deeply conflicted for men, who were experiencing one of the many crises that periodically afflict masculinity itself. The film itself seems a bit confused in its messaging, for while it seems to suggest that men would do better to seize their own agency, the members of the various fight clubs instead fall under the hypnotic sway of Tyler Durden (who is, of course, played by Brad Pitt and is also the nameless Narrator’s alter-ego). In the end, the film tries to be a bit. 

As a director, Terrence Malick is well-known (one might say infamous) for the extent to which his films act meditation more than storytelling, per se, and Tree of Life is one of his most beautiful but also most perplexing movies. On one level, it seems to be about a middle-aged man and his attempts to come to terms with his family and their past, while on another, deeper level, it’s about life and the meaning of the universe. It’s all quite evocative in execution, but the elliptical nature of the narrative can sometimes leave the viewer feeling more frustrated than philosophical. 

While author Stephen King might not have liked Stanley Kubrick’s adaptation of his novel, there’s no question that The Shining has come to be seen as not only one of the director’s best but also a canonical piece of horror filmmaking. As with so many other confusing movies, the ending is what proves to be particularly perplexing, as it seems to suggest (according to one reading) that the main character, Jack, is some sort of reincarnation of someone who once worked at the hotel. While, on the one hand, something is exciting about how this opens the film up to multiple interpretations, it also ends up being a bit of a frustrating conclusion, including for King himself. 

Even though The Prestige  might be one of director Christopher Nolan's most narratively straightforward films, focusing as it does on a pair of 19th-century magicians engaged in a bitter rivalry. However, as the story goes on, it becomes clear that there's much more to their efforts to perfect a teleportation illusion than meets the eye. The reveal at the end is rather confounding, as it seems to go against the story that audiences have led to believe they've been watching. Furthermore, like most other Nolan films–and appropriately, given the subject–there are quite a few narrative sleights-of-hand, meaning that it's easy for a viewer to get confused if they're not paying rigorous attention to what's happening.

Andrei Tarkovsky’s Solaris pushes the audience to think in new and sometimes challenging ways about themselves and their place in the universe. At first, the film seems as if it’s going to be a simple story about a psychologist who goes to a space station to examine its crew, but it becomes clear that it’s something far more sinister at work. Just as the character begins to lose his grip on reality, the audience also begins to question the nature of what they are seeing. The ending acts as a sublime challenge to narrative and psychological coherence. 

Last Year at Marienbad delights in being elliptical and keeping the audience guessing as to what it is that they are actually watching. At first blush, it appears to be about a man and a woman who have reunited at an opulent hotel, but Last Year constantly plays with expectations and narrative logic, keeping the viewer as off-balance as the characters. It’s a film that is not for the faint of heart, but it is nevertheless quite a rewarding film and philosophical experience for those who want a film that doesn’t talk down to its audience but instead aims to challenge them to think differently about time, space, and memory.

Bryan Singer’s The Usual Suspects is, like its central antagonist, Keyser Söze, a bit of a riddle wrapped in an enigma. There’s no question that it features some sharp direction from Singer, nor is there any question that Kevin Spacey delivers a remarkably chilling performance. At the same time, the film gets a little too caught up in the twists and turns of its narrative. The final twist does work in its own way, but it may leave many viewers wondering just how much they can trust their own impressions of what happened in the movie that they have just seen.

Cats might have the dubious distinction of being one of the most poorly-reviewed musicals to have ever graced the big screen. Adapted from the long-running and enormously successful stage play, this 2019 film was met with almost universal derision by critics and audiences alike, particularly for its glaringly bad use of CGI instead of costumes. Many things remain befuddling about this film, from the presence of titanic talents like Judi Dench and Ian McKellen to how it managed to make it to theaters in its present form. However, its confusing nature might prove beneficial, as it will probably become one of those films seen as so bad that it's good. 

Stanley Kubrick’s 2001: A Space Odyssey continues to astound and enchant, and it’s easy to see why. It’s the perfect marriage of form and content, with the epic sweep of the big screen working in tandem with the film’s weightier philosophical musings. However, it has to be said that the latter can sometimes be a bit overwhelming for a casual viewer, particularly since 2001 focuses much more on ideas than it does on the plot per se. What’s more, it contains numerous enigmas and questions that it never entirely answers, in the end leaving the viewer more than a little confused, and the ending remains as perplexing now as it was when the film was first released.

Christopher Nolan has long shown a love of playing with narrative and how viewers make sense of film as a medium. Memento  remains one of his most thought-provoking films for exactly this reason, and its story about Leonard Shelby (played by Guy Pearce), who suffers from short-term memory loss, continually plays with expectations. Indeed, it sometimes seems as if one has to have a notebook and pen in hand to keep track of what’s happening in a film in which the story itself is disjointed. Though it can be incredibly confusing at times, there’s also no question that Memento is Nolan at his best, and the payoff makes all of the bewilderment worth it.

Eraserhead is very difficult to summarize, but this makes its own kind of sense, considering it was directed by David Lynch. Lynch has made a career out of crafting challenging and difficult films, and they don’t come much more confusing than Eraserhead. Deeply surreal and unsettling, it defies easy summarizing. It is, ultimately, a film that relies very heavily on the surreal nature of its imagery and its startling sound design to engender a feeling in the audience rather than the traditional narrative techniques expected of cinema.

Many classic Hollywood films remain easy for even a casual film viewer to follow, thanks to the firm rules of narrative the studio system tended to follow. Every so often, however, a film managed to emerge that was as challenging in its form as in its content, and perhaps the most notable example is The Big Sleep. Though, these days, the film is known for its pairing of Humphrey Bogart and Lauren Bacall, it still makes for a befuddling viewing experience, particularly if one watches the original version from 1945 (rather than the re-release). However, since it is a film noir, a genre known for its  

Films don’t come much more confusing than Synecdoche, New York, which is one of those films that literalizes the extent to which cinema can challenge how audiences make sense of the world and their place in it. Philip Seymour Hoffman delivers one of his typical strong performances as theater director Caden Cotard, who begins to construct a production that will capture the everyday. The film's brilliance lies in its ability to make the viewer question their own grasp on the difference between reality and fiction, even if this is also one of the most confusing aspects of its story.