10 Most Challenging Movies of All Time

To stay on the topic of long movies, though, you’ve also got some of the titles below that are epic in runtime, and often ambition, but prove a good deal more difficult to sit through. Some of these challenging movies are good, while others maybe not so much. They're all impressive, though, each playing a role in pushing cinema forward or at least endeavoring to showcase things that most movies don’t usually do.

10 'Heaven's Gate' (1980)

There’s a lot to be impressed by when it comes to Heaven’s Gate, and the epic is definitely better than many gave it credit for being when it first came out (it’s one of those quintessential “critics got it wrong at the time” movies). It should still be stressed, though, that it’s not an easy watch, and even if it is for some people, it remains probably not for everyone.

Heaven’s Gate is about a conflict over land in Jackson County, Wyoming that escalates into an all-out war, with numerous people being caught up in a whole heap of violence, and nothing really ending up well for anyone. It does for the Western genre what Michael Cimino’s previous film, The Deer Hunter, did for war movies, though Heaven’s Gate is even longer, not to mention debatably more despairing.

9 'Céline and Julie Go Boating' (1974)

For some reason, Céline and Julie Go Boating is over three hours long, and it mostly proves meandering and without intention in ways that feel intentional. It’s full-on arthouse, without much by way of a discernible plot, since the two titular characters go on a series of misadventures and keep crossing over into different genres, more or less. But those genres are all part of their life, or something.

It’s profound, or it’s nonsense, or it’s a bit of both. You take what you can from a film like Céline and Julie Go Boating, and you'll probably feel fortunate about taking whatever scraps you can, in terms of meaning and understanding. Or, if you click with what the movie’s doing stylistically and with its atmosphere, then maybe it’ll be kind of enjoyable and perplexing in that manner.

8 'Babylon' (2022)

Babylon is kind of misunderstood, to an extent that makes it fair to assume the movie is challenging, and then that’s furthered by the fact that it’s also long, like the other movies being mentioned here, with the runtime being over three hours. There are a bunch of characters followed throughout, and all of them are wrapped up in some kind of Hollywood-related life at a time of change, with the transition from the silent to talkie era being what Babylon is mostly concerned with.

Things do get messy, in terms of Babylon celebrating cinema to some extent, and exploring the excitement that can come from being involved in some sort of massive creative production, all the while the industry itself is also shown to be hugely destructive – and even deadly – to individuals. By design, you're left not really knowing where the line should be drawn, or even if a line can be drawn, which is what Damien Chazelle also explored with Whiplash, though people seemed to understand that one a little bit more. Hopefully, Babylon’s time will come, once enough years have passed.

7 '1900' (1976)

For as disturbing as the likes of Heaven’s Gate and Babylon got at times, they both look kind of mild in comparison to 1900, and then you factor in this movie being over five hours long, rather than hovering around the three-hour mark, and you inevitably get a more challenging epic. The ambition here is definitely admirable, though, because 1900 begins around the titular year, and then keeps going forward, decade by decade, covering much of the first half of the 20th century.

You get difficult political ideas explored here, a variety of depressing social issues touched upon, and then some characters who are willing to do genuinely mortifying things. 1900 is disturbing in ways that can’t really be described without some kind of content warning, with its visuals being genuinely shocking and explicit at times. The movie’s about some intense things and nasty people, so it’s not too surprisingly intense and kind of nasty to watch at times itself.

6 'Hard to Be a God' (2013)

A Russian movie that doesn’t feel very science fiction-heavy on the surface, even though it is very much a work of science fiction, Hard to Be a God takes place on a planet that gets visited by some Earth scientists. The people on the planet are going through a medieval era, or their equivalent of that, and so that’s what makes the film feel almost like a gritty fantasy movie, or maybe a down-and-dirty historical drama, like the lesser-known Paul Verhoeven movie Flesh and Blood.

As the title suggests, Hard to Be a God has some of the scientists playing God while on this planet, and then there are indeed hardships with doing that, both for the planet’s population and the scientists themselves. It’s all ugly on a visual and emotional front, and then the film’s something of an endurance test, too, with its runtime that’s only a few minutes shy of three hours.

5 'Satantango' (1994)

Satantango is, above anything else, a movie that goes for seven hours. If you can find one review of Satantango that doesn’t mention the runtime, then you should next set your sights on finding the Holy Grail, El Dorado, or the lost city of Atlantis, because you're a natural at the whole finding things thing. The length here is the point, with Satantango immersing you in boredom and despair for an undeniably long time.

It’s immersive, for better or worse. You do feel the intensity of the distressing lifestyle the people in this movie have found themselves stuck in, and then there’s a certain numbing quality with the daunting length that makes you understand why they’ve all resigned themselves to it. If that makes the movie good, then it’s a good movie. Whether you should watch Satantango, on the other hand… uh… Just don't, honestly. It's not worth it. People only watch this so they can brag that they have. You could feel everything the movie's going for if it were half (or maybe even just one third) of its actual length.

4 'Eros + Massacre' (1969)

More or less two experimental movies in one, with both being interwoven in a way that makes the whole thing feel even more experimental, Eros + Massacre is dense, confusing, and – perhaps understandably – somewhat obscure. People in the 1960s are looking into the life and times of an anarchist from the 1920s, which is one story, and then the other story is that stuff happening in the 1920s.

The whole novel approach to being a biographical/historical movie of sorts might make Eros + Massacre feel a little like Mishima: A Life in Four Chapters, which is another Japanese-language movie that’s kind of challenging, but Eros + Massacre is another level of challenging altogether. It’s also the length of two “ordinary” movies, being 216 minutes all up (and you do very much feel that immense runtime).

3 'Out 1' (1971)

Out 1 was directed by the same guy behind Céline and Julie Go Boating, Jacques Rivette, and it’s arguably even trickier to recommend, even if it’s a more compelling film. You just need an almost obscene amount of time to watch the whole thing, because Out 1 has a runtime of 743 minutes… in other words, it’s a bit over 12 hours long. To make it sound a little less daunting, it is split into eight parts, but still.

Each part on its own is pretty much feature-length. And they all add up to something, maybe? The point of Out 1 seems to be making you feel paranoid for a very long time, and the excessively long runtime adds to that sense of madness and borderline delirium. If you never find the time for it, that’s okay, but if you do find the time, and you like challenging and/or out-there movies, then it’s probably worth exploring.

2 'Jeanne Dielman, 23, quai du Commerce, 1080 Bruxelles' (1975)

There’s no humor or fun to be found in Jeanne Dielman, 23, quai du Commerce, 1080 Bruxelles, even compared to most of the other movies mentioned here. It might well be even slower and more (intentionally) tedious than Satantango, though it’s “only” three and a half hours long, rather than approximately seven hours, so that’s something.

You’d potentially be forgiven for thinking Jeanne Dielman, 23, quai du Commerce, 1080 Bruxelles was longer than three and a half hours, though, because it very patiently shows a woman’s daily routine across three days, and her life is defined by a lack of excitement, variety, and warmth. The whole thing’s cold and depressing, all by design, driving home a certain reality of life for many people in a way that’s admirable as an artistic statement, yet kind of awful as a movie. Yes, that’s the point, but whatever, you know? There are plenty of challenging movies with more interesting sights and sounds to offer out there.

1 'Inland Empire' (2006)

Inland Empire isn't really the ultimate David Lynch movie in terms of quality, because plenty of his other movies are stronger (it’s not hard to argue as much, at least), but Inland Empire is the most Lynchian of all the David Lynch movies. It’s the ultimate one in that regard, as it’s the most head-spinning, harrowing, and visually bold, all the while also being his longest movie at exactly three hours in length.

It’s got some thematic similarities to Lost Highway and Mulholland Drive, yet it disappears into mystery and surrealism at a much more rapid rate, and stylistically, it’s also (intentionally) not nearly as eye-catching to look at. Inland Empire feels very grimy and lo-fi in a way that’s easier to admire than enjoy. As for the plot… who knows? It’s whatever you want it to be, whether that’s a lot or a little or somewhere in between. Huh?