473 Best Challenging Movies to Watch (Page 18)

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One of the cinema’s most noble roles is to challenge pre-conceived perceptions and tackle difficult questions about humanity and the world. Here are some of the most important and topically challenging movies to stream right now.

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, 2023

Nanpakal Nerathu Mayakkam might not immediately make sense to audiences new to director Lijo Jose Pellissery, but it’s still an interesting film that depicts Tamil culture. Also known as Like an Afternoon Dream, the contemplative bilingual film is centered around a prejudiced Malayali tour guide who wakes up as another man, specifically someone fluent in Tamil, and walks into the nearby village. Through vignettes focused on the village inhabitants, the film slowly unravels the dynamics between each of the villagers, flitting back to the tour bus on occasion to see how they’re faring. While some of the comedy goes over viewer’s heads, especially for people unfamiliar with the state, the slow-paced film feels like a fond memory from Pellissery. The film doesn’t explain anything at all, in the same way strange dreams refuse to do.

Genre: Comedy, Drama, Fantasy

Actor: 'Poo' Ram, Ashokan, Ashwanth Ashokkumar, G. M. Kumar, Mammootty, Namo Narayanan, Rajesh Sharma, Ramachandran Durairaj, Ramya Pandian, Ramya Suvi, Thennavan, Vipin Atley

Director: Lijo Jose Pellissery

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, 1995

Best known for landmark cyberpunk anime Akira, Katsuhiro Otomo crafted strange and terrifying visions of a world that has not yet come, imagining technology that surpassed that of today, but in much pessimistic light compared to that of the genre. Three of his manga short stories are depicted in Memories, with Otomo partnering with Kōji Morimoto and Tensai Okamura to direct each segment, and with Satoshi Kon in writing, just before Kon’s own iconic surrealist films. Kon-written Magnetic Rose has been universally acknowledged as the best of them, being much more emotionally poignant, but the other two does have its charms, as Stink Bomb takes a relatively silly premise to its fairly logical, but scary conclusion, and Cannon Fodder takes the beauty of Otomo’s art into such a hollow and ugly world. All three deliver terrifying omens of death through technology used against the everyday man, whether by accident or design.

Genre: Animation, Fantasy, Science Fiction

Actor: Ami Hasegawa, Gara Takashima, Hidetoshi Nakamura, Hideyuki Hori, Hisako Kyoda, Hisao Egawa, Kayoko Fujii, Keaton Yamada, Keiko Yamamoto, Kenichi Ogata, Koichi Yamadera, Masato Hirano, Michio Hazama, Nobuaki Fukuda, Osamu Saka, Ryoichi Tanaka, Ryuji Nakagi, Shigeru Chiba, Shozo Iizuka, Takkô Ishimori, Tetsuya Iwanaga, Tomoko Ishimura, Tsutomu Isobe, Yuu Hayashi

Director: Katsuhiro Otomo, Koji Morimoto, Tensai Okamura

Rating: PG-13

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, 1996

Many people have forgotten that representation and diversity in media isn’t meant just to fill a quota or to signal virtue– the push for it is in response to the way many of these stories were silenced, repressed, and shut out. Lilies might have been overlooked for quite a while, but its 2023 restoration has thankfully enabled more viewers to watch the tale of an imprisoned gay man finally telling his story, turning the tables on a long overdue confession. Michel Marc Bouchard adapts his play through this play-within-a-film, with director John Greyson playing with the confession booth as a viewing booth for both the bishop and the audience to get fully immersed in a love triangle a century ago, juxtaposed with motifs of martyred Catholic saints and French lilies and fire. Lilies is a well-crafted and deeply emotional masterpiece.

Genre: Drama, Fantasy, Romance

Actor: Alain Gendreau, Aubert Pallascio, Brent Carver, Danny Gilmore, Gary Farmer, Ian D. Clark, Jason Cadieux, John Dunn-Hill, Khanh Hua, Marcel Sabourin, Matthew Ferguson, Michel Marc Bouchard, Pierre Leblanc, Rémy Girard, Robert Lalonde

Director: John Greyson

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, 2023

Surreal, off-putting, and extremely disturbing, Infinity Pool plays with the concepts of cloning and the death penalty to craft an examination on colonial tourism. It’s a thematically rich horror film, with hazy neon-lit sex scenes and absolutely terrible behavior, enabled by their wealth and advanced technology that could have been put to better use. Mia Goth, in particular, is strikingly unhinged, as Gabi taunts and lures James into bigger and more terrible crimes, crimes that he can only pay off with the wealth of his father-in-law. And Alexander Skarsgård as James believably gets sucked into this extremely libertine lifestyle, fuelled by the nepotistic anxiety of not living up to his own potential. The film presents a scary notion that pushed by wealth and playground tactics, one will willingly kill their own conscience, again and again, to belong to their cohort.

Genre: Horror, Science Fiction, Thriller

Actor: Alexander Skarsgård, Alexandra Tóth, Amanda Brugel, Amar Bukvić, Caroline Boulton, Cleopatra Coleman, Gergely Trócsányi, Géza Kovács, Jalil Lespert, Jeff Ricketts, John Ralston, Kamilla Fátyol, Mia Goth, Roderick Hill, Romina Tonković, Thomas Kretschmann, Zijad Gračić

Director: Brandon Cronenberg

Rating: R

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, 2021

Great Freedom is not an easy watch. Apart from the quiet stretches of time and the claustrophobic confines of its prison setting, it also has its lead, Hans Hoffman (played with delicate force by Franz Rogowski) imprisoned again and again and again, unjustly treated like dirt by both his warden and fellow inmates.

But as a Jewish gay man who has lived through the war, Hans is no stranger to these trappings. As such, he takes each day as it comes, open to love, pleasure, and friendship, or at least the potential of these, despite the circumstances. And so Great Freedom is also hopeful and romantic, glimmering with the human tendency to not just survive but to live. Slow but compelling, subdued but powerful, Great Freedom is an affecting balancing act that's well worth watching. 

Genre: Crime, Drama, Romance, War

Actor: Alfred Hartung, Andreas Patton, Anton von Lucke, David Burnell IV, Fabian Stumm, Franz Rogowski, Georg Friedrich, Thomas Prenn, Thomas Stecher, Thomas Wehling

Director: Sebastian Meise

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, 1997

See, usually, when American violence in media is critiqued, it’s usually through analytic studies or overly exaggerated lectures stirring moral panic. Instead of doing this, however, auteur Michael Haneke decided to surpass the crime genre, playing with the form and emotions in Funny Games. It’s terrifying, not because it immediately delves into the violence, but because it starts off with an ordinary, innocuous visit, that gradually escalates into an unpredictable home invasion where two teenagers inflict needless violence in such a scary yet spectacular way, even involving the viewer into their shenanigans. Ironically, this led to Haneke creating a shot-for-shot American remake of this same story, but Funny Games’ break in form made Haneke a director to remember, as he started to film outside his native Austria after the standout thriller.

Genre: Drama, Horror, Thriller

Actor: Arno Frisch, Christoph Bantzer, Doris Kunstmann, Frank Giering, Stefan Clapczynski, Susanne Lothar, Susanne Meneghel, Ulrich Mühe

Director: Michael Haneke

Rating: R

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, 1994

With many iterations of Faust, Jan Švankmajer’s own take on the deal with the devil isn't absolutely terrifying, and can feel bizarre, sometimes even goofy, to those unfamiliar with the animation director. However, Lekce Faust is quite creepy, as he brings the legend to modern day Prague with a mysterious map and visually disturbing puppets that brilliantly mixes live action with stop-motion and claymation into folklorish cinematic magic. It's not the most faithful rendition of the classic tale, but it's one of the most inventive, proving that while the deals like this pop up only in past folklore, the devil still lingers in fairly absurd ways.

Genre: Animation, Drama, Fantasy

Actor: Antonín Zacpal, Jan Kraus, Jiří Suchý, Petr Čepek, Petr Meissel, Vladimír Kudla

Director: Jan Švankmajer

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, 2020

In the years since Fan Girl's original release in the Philippines, its ultimate message and execution has become polarizing: is it enough that the film shows the corruption of a parasocial relationship into an abusive one, without offering much hope? Is its vision of justice actually constructive or disappointingly limited? No matter where you fall, it's exciting that a movie can stir up these kinds of questions through a bizarre dynamic between characters, in a place that's clearly set somewhere between reality and delusion. The narrative is circular and frustrating for a reason—a constant push and pull as the titular fan girl keeps getting drawn back into the celebrity's orbit—and the film only grows more disturbing with each repetition.

Genre: Drama, Thriller

Actor: Bea Alonzo, Camille Penaverde, Charlie Dizon, Gie Onida, Micko Laurente, Milo Elmido Jr., Mina Cruz, Paulo Avelino, Sheenly Gener

Director: Antoinette Jadaone

Rating: PG-13

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, 1991

World War II changed the fate of many countries, but most prominently that of the European continent and the United States of America. Though late to the battlefield, America was one of the victors that occupied Germany after the war, and it's this tension and setting that is at the center of Lars von Trier’s lone war drama Europa. Alternatively known as Zentropa in some territories, the film is inspired by Hollywood noir, from the black and white film to the femme fatale, but the film takes more experimental routes, starting off with lulling the viewers in a hypnotic trance, and later playing on with rear-projection and multiple layers for surreal effect. It takes noirish cynicism on a ride, exaggerating history but nonetheless reflects the way this memory is formed in the cinema of its respective countries. Europa is a fascinating breakdown of an idealist that hasn't gone through the same terrors, one that still lingers in today’s consciousness.

Genre: Crime, Drama, Thriller

Actor: Baard Owe, Barbara Sukowa, Benny Poulsen, Claus Flygare, Eddie Constantine, Else Petersen, Erik Mørk, Erno Müller, Ernst-Hugo Järegård, Hardy Rafn, Henning Jensen, Holger Perfort, János Herskó, Jean-Marc Barr, Lars von Trier, Max von Sydow, Udo Kier, Vera Gebuhr

Director: Lars von Trier

Rating: R

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, 1988

As a woman, it’s risky enough to trust a male gynecologist, but to have him seduce, manipulate, and experiment on you? That’s a horror all on its own, but Dead Ringers operates on several levels beyond the political. It’s also psychological and sexual, and because this is a Cronenberg film, it’s done with an unsettling amount of gore. But perhaps the most impressive part of Dead Ringers (apart from Irons convincingly playing twins with just a deft change of inflection, of course) is the eroticism it contains. This element seems to be lacking in many films nowadays, or forced in a way that feels even more uncomfortable than gratuitous sex. The fact that this Reagan-era movie was and continues to be subversive says a lot about how potent it is, and how unfortunately slow we’ve been to tolerate sensuality in film.

Genre: Horror, Thriller

Actor: Barbara Gordon, Bob Bainborough, Damir Andrei, David Cronenberg, Dee McCafferty, Denis Akiyama, Denise McLeod, Geneviève Bujold, Hadley Kay, Heidi von Palleske, Jacqueline Hennessy, Jane Luk, Jeremy Irons, Jill Hennessy, John Bayliss, Lynne Cormack, Marsha Moreau, Murray Cruchley, Nicholas Rice, Nick Nichols, Rena Polley, Richard W. Farrell, Shirley Douglas, Stephen Lack, Warren Davis

Director: David Cronenberg

Rating: R

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, 2023

We all learned that it’s good to have a free press, but most of us rarely consider why it’s good, why we should fight for it, and how to do so, in the first place. Bad Press tackles one such fight, specifically the battle for free press in the Muscogee Nation, and while it only tackles government control specifically, the documentary is a reminder of how fragile press freedom can be, broken in mere minutes, and how long and difficult it is to get it back. Has Bad Press figured out how to bring back free press? Perhaps, though the struggles were made much more murky with the way fake news outlets take advantage of the narrative, the way politicians keep their silence to maintain innocence, and the way the masses could have voted against it. But nonetheless, Bad Press was a necessary reminder of how much could have been lost.

Genre: Documentary

Actor: Angel Ellis

Director: Joe Peeler, Rebecca Landsberry-Baker

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, 1988

While Lewis Carroll's Alice in Wonderland is widely considered a classic, there’s just something inscrutable, mysterious, and even a bit weird about the tale. Czech director Jan Svankmajer's version takes a distinctly unsettling approach, with everything but normal-sized Alice animated into creepy stop-motion, including, but not limited to, cards, puppets falling apart, and actual dead animals, and with every dialogue coming literally from Alice’s mouth, but it’s through this approach that makes the fantastical novel more like a strange dream rather than the Disney-fied fairy tale we’ve come to know. Něco z Alenky is a refreshing take that finally acknowledges the dark side of Alice in Wonderland.

Genre: Adventure, Animation, Fantasy

Actor: Kristýna Kohoutová

Director: Jan Švankmajer

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, 2021

In the Mexican film A Cop Movie, director Alonso Ruizpalacios mixes fact and fiction, documentary and narrative, to tell the tale of Teresa and Montoya, two police officers whose dreams are dashed by the corruption of their trade and who, eventually, find love and comfort in each other.

Ruizpalacios takes thrilling risks in structuring this genre-bending story—cutting stories into parts, jumping back and forth between the harrowingly real and captivatingly non-real. For all the experimental maneuvers he makes, however, the through-line is always Teresa and Montoya: particularly, their love for each other and for an institution that should have, in an ideal world, supported them and the people they vowed to protect. 

To its credit, instead of merely humanizing the controversial police force, A Cop Movie adds some much-needed nuance to the big picture. At the end of the day, they’re no different than any other underpaid laborers working desperately to make end meets. A Cop Movie doesn’t gloss over the fact that the police, like so many other workers, are stuck in a rotten system that’s long overdue for a major overhauling. 

Genre: Action, Crime, Documentary, Drama, Thriller

Actor: Carlos Corona, Juan Carlos Medellin, Leonardo Alonso, Mónica Del Carmen, Olivia Lagunas, Raúl Briones, Yoshira Escárrega

Director: Alonso Ruizpalacios

Rating: R

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