497 Best Challenging Movies to Watch (Page 19)

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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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, 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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, 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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, 2023

It can be very frustrating to watch something, hoping that the show, play, or film would be worth watching, and find yourself feeling worse after the experience. Most of us end up just changing the channel, leaving the theater, or finding something else to watch, but instead of doing any of this, Yannick depicts the titular audience member interrupting the show with a gun. You can already imagine how tense the situation is, but Quentin Dupieux infuses a comedic, meta touch in the way Yannick questions and holds the audience hostage, as his conversations with them and the cast reveal the different expectations we have from art.

Genre: Comedy, Drama

Actor: Agnès Hurstel, Blanche Gardin, Caroline Piette, Charlotte Laemmel, Félix Bossuet, Jean-Paul Solal, Laurent Nicolas, Lucie Gallo, Mustapha Abourachid, Pio Marmaï, Raphaël Quenard, Sava Lolov, Sébastien Chassagne, Stéphane Pezerat

Director: Quentin Dupieux

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, 1995

When reading the premise, Tokyo Fist seems, at first glance, like the primordial eclectic mix of Challengers and Fight Club, with tennis swapped for boxing, and with sweat swapped for bruises. The film is entirely centered on a love triangle spurred on by a sport, with both players out to settle their rivalry, triggered again by a girl. However, being directed by cyberpunk horror auteur Shinya Tsukamoto, Tokyo Fist takes on a more visceral approach, with repressed resentment only able to be released through beating the hell out of each other, beating the hell out of themselves, and through bloodying both their fists and their opponents’ faces. It gets avant garde at certain moments, but Tokyo Fist is a sports horror ahead of its time, and an unexpected, underrated film from the man behind cult classic Tetsuo: the Iron Man.

Genre: Action, Drama, Thriller

Actor: Chu Ishikawa, Julie Dreyfus, Kaori Fujii, Koichi Wajima, Kôji Tsukamoto, Naomasa Musaka, Naoto Takenaka, Nobu Kanaoka, Shinya Tsukamoto, Tokitoshi Shiota, Tomorowo Taguchi

Director: Shinya Tsukamoto

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, 2014

Despite the subject matter, 2014 Malian drama Timbuktu still spots some humor through simple contradiction– straightforwardly depicting the occupying force enforcing certain rules upon a city, but not themselves, and with the city biting back in their own way, pointing out the silliness themselves. It’s these raw moments that lightens the entire film, humanizing both the militant group and the city inhabitants, but it’s also the reason why the moments when that lightheartedness is broken, the punishments end up becoming harsher, strikes harder than usual. It’s that uncertainty that keeps the audience on its toes, and that keeps the film from mining melodrama from the real life occupation. Timbuktu just simply highlights the foolishness of imposing an ideology to snuff out everyday culture.

Genre: Drama, War

Actor: Abel Jafri, Fatoumata Diawara, Hichem Yacoubi, Ibrahim Ahmed, Kettly Noël, Layla Walet Mohamed, Toulou Kiki

Director: Abderrahmane Sissako

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, 2016

Based on the short story “God Sees the Truth, But Waits” by Leo Tolstoy, The Woman Who Left is a film about people with nowhere to go. Set in 1990s Philippines, the film follows Horacia, an ex-convict seeking revenge on her former lover who masterminded her unjust 30-year imprisonment. Along the way, she meets various people—a hunchback balut vendor, vagabonds, and an epileptic trans woman, among others—all downtrodden in their own unique ways and united only by their nightly wanderings, with whom Horacia’s true nature is revealed and reconfigured with every encounter.

Lav Diaz’s signature slow cinema minimalism and sharp chiaroscuro lighting allow for a meditative experience, further enhancing the film’s immersive quality. Despite its bleak atmosphere, The Woman Who Left remains hopeful amidst moral quandaries, where things eventually fall into their rightful place, albeit in unexpected ways.

Genre: Drama

Actor: Charo Santos-Concio, John Lloyd Cruz, Kakai Bautista, Lao Rodriguez, Mae Paner, Michael De Mesa, Nonie Buencamino, Shamaine Buencamino

Director: Lav Diaz

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, 2009

No one likes to be replaced. Even when it gets difficult, hardwork and years put in effort to take and keep these roles makes it feel precious, and that’s exactly how househelp Raquel feels in The Maid. It’s a funny domestic comedy, with a scowling Catalina Saavedra ready to protect the role she’s held onto for years, but Saavedra and writer-director Sebastián Silva crafts an empathetic, realistic character study of a woman so worn down from poverty, power imbalance, and having had no breaks that the rare instance of compassion feels like a threat. La Nana doesn’t quite critique the entire system that keeps Raquel in her role, but it’s a rare film that acknowledges the importance of rest and empathy in order to feel human.

Genre: Comedy, Drama

Actor: Agustín Silva, Alejandro Goic, Andrea García-Huidobro, Anita Reeves, Catalina Saavedra, Claudia Celedón, Claudia Paz, Delfina Guzmán, Juan Pablo Larenas, Luis Dubó, Luis Wigdorsky, Mariana Loyola

Director: Sebastián Silva

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, 2023

Feminism has made plenty of strides in multiple areas, but even in the era of free love, talking about sex was difficult, and certain figures were dismissed just because of it. The Disappearance of Shere Hite reexamines the titular forgotten feminist figure that simply focused on the female orgasm, giving a second look at her immediate rise and fall in the American media, and the reasons for her leaving the country. With Dakota Johnson’s soft voice, an excellent selection of archival footage, and Hite’s deeply personal words, the film paints a portrait of a mild-mannered, self-possessed woman, but it also reveals the heartbreakingly repetitive vitriol that affects these open discussions today.

Genre: Documentary

Actor: Dakota Johnson, Shere Hite

Director: Nicole Newnham

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