497 Best Challenging Movies to Watch (Page 16)

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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

Unlike plenty of time torn films, Maboroshi is the kind of film that doesn’t have a straightforward explanation for the town of Mifuse standing still in time. But even when it doesn’t have a logical reason, the way the film unfolds has a distinct feeling as it explores the illusions the town either could cling to, or release to grow. This kind of storytelling would be familiar to fans of the prolific screenwriter Mari Okada, who just started directing in 2018 with Maquia: When the Promised Flower Blooms, but even those new to her work would appreciate the pure emotion driving Maboroshi, if they can let go of reality and enjoy MAPPA’s exquisite art for a moment.

Genre: Animation, Drama, Fantasy, Romance

Actor: Ayaka Saito, Daiki Kobayashi, Junya Enoki, Kento Hayashi, Koji Seto, Maki Kawase, Misaki Kuno, Reina Ueda, Setsuji Sato, Taku Yashiro, Tasuku Hatanaka, Yukiyo Fujii

Director: Mari Okada, Seimei Kidokoro

Rating: PG-13

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, 2014

With laws, education, and modern day systems, it seems like the modern man has some means for recourse, at least more than the average person centuries ago. However, despite this, injustices still remain. Leviathan depicts Kolya, a modern day Job, set out to keep his land from the clutches of a corrupt mayor. It’s bleak and depressing, somewhat neorealistic as Kolya goes through various hardships due to political greed, but there’s some wry sense of humor, one that bitterly points out how much hasn’t changed since biblical times. While it’s quite long, Leviathan is likely to move most viewers to tears, and maybe to shots of vodka, due to its depiction of the everyday man.

Genre: Crime, Drama

Actor: Aleksei Zharkov, Aleksey Pavlov, Aleksey Rozin, Aleksey Serebryakov, Anna Pereleshina, Anna Ukolova, Dmitriy Bykovskiy-Romashov, Elena Lyadova, Igor Savochkin, Igor Sergeev, Lesya Kudryashova, Margarita Shubina, Marianna Shults, Mariya Shekunova, Olga Lapshina, Roman Madyanov, Sergey Bachurskiy, Sergey Borisov, Sergey Murzin, Sergey Pokhodaev, Valeriy Grishko, Vladimir Vdovichenkov

Director: Andrey Zvyagintsev

Rating: R

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, 1987

When falling in love with another, or when another person falls in love with you, the relationship is formed by the ideas in your and their heads, specifically about your dynamic, your respective personalities, and the potential outcome of this love. Law of Desire is centered on this idea, unfolding through a chaotic gay love triangle that demonstrates the ways the ideas and fantasies can differ. And as the characters inevitably go through fairly melodramatic reactions when they realize the desires of another person, in the most colorful fashion (literally and figuratively), Pedro Almodóvar creates an amusing and daring examination of the genre it’s inspired by.

Genre: Comedy, Drama, Romance, Thriller

Actor: Agustín Almodóvar, Alfonso Vallejo, Antonio Banderas, Bibiana Fernandez, Carmen Maura, Eusebio Poncela, Fernando Guillén, Fernando Guillen, Fernando Guillén Cuervo, Germán Cobos, Germán Cobos, Helga Line, Lupe Barrado, Manuela Velasco, Marta Fernandez Muro, Miguel Molina, Nacho Martinez, Pedro Almodóvar, Rossy de Palma, Victoria Abril

Director: Pedro Almodóvar

Rating: NC-17

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, 1995

Upon the first few minutes of Institute Benjamenta, or This Dream People Call Human Life, it’s obvious that the Brothers Quay’s first live-action film is highly unusual. First, it’s entirely black and white, with embellished, serif subtitles translating the initial German. Second, many of the film’s shots take the form of moody, gothic close-ups, reminiscent of 1920s silent films, like when Johannes examines his new pupil’s health, or when Lisa directs Jakob with an animal’s hoof next to his cheek. And third, the plot itself is strange, as the students are taught not to think anything of themselves, with only Jakob questioning their instruction. But there’s a certain beauty in the surreal approach the Brothers Quay takes in adapting the Swiss-German novel, a certain intuitive feel that allows the story to expand past its stilted movement, restrained frames, and the school’s oppressive tutelage. Institute Benjamenta is bizarre, but it’s undeniably a fascinating film, even at its most disturbing.

Genre: Drama

Actor: Alice Krige, César Saratxu, Daniel Smith, Gottfried John, Jonathan Stone, Joseph Alessi, Mark Rylance, Peter Lovstrom, Uri Roodner

Director: Stephen Quay, Timothy Quay

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, 1998

Comparisons are easy between friends and within peer groups, but the comparison that is most immediate is that between you and your sibling, especially when they wound up more successful than you are. Hilary and Jackie captures that experience between two real-life musical sisters, but the comparison is so much more difficult as Jackie shot to cellist superstardom, even with under the same musical beginnings as her less known sister Hilary. It’s flawed, but it’s deeply personal, diving into their shared anxieties from two different lives, and it’s surprisingly well-rounded, perfectly halved between the sisters’ perspectives led excellently by Rachel Griffiths and Emily Watson. Hilary and Jackie is not comfortable to watch, especially during Jackie’s later years, but it’s a daring portrait of a difficult, but still loving, sibling relationship.

Genre: Drama, Music

Actor: Anthony Smee, Bill Paterson, Carla Mendonça, Celia Imrie, Charles Dance, David Morrissey, David Shimwell, Delia Lindsay, Emily Watson, Grace Chatto, James Frain, Jon Rumney, Keylee Jade Flanders, Kika Mirylees, Linda Spurrier, Maggie McCarthy, Nick Haverson, Nyree Dawn Porter, Rachel Griffiths, Robert Rietti, Rupert Penry-Jones, Vernon Dobtcheff

Director: Anand Tucker

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, 2024

Before she captivated the film world with her performance in Scorcese’s crime drama Killers of the Flower Moon, Lily Gladstone starred in Erica Tremblay’s feature film debut Fancy Dance, earlier in 2023. It’s a tragic drama, wherein Gladstone portrays Jax, a lesbian woman dealing with the government that failed to find her sister, and that currently seeks to transfer her niece’s custody to her white father. But it’s also an uplifting drama, one that celebrates the connection between Jax and her niece Roki, the Cayuga culture and language, and the connection with their community and tribe that continues to persist despite state disenfranchisement. Pacing issues do make the film a tad rushed, but nevertheless, Fancy Dance is a subtle and poignant debut, made much more grounded with the excellent lead performances.

Genre: Drama

Actor: Arianne Martin, Audrey Wasilewski, Colleen Elizabeth Miller, Cory Hart, Crystle Lightning, Isabel Deroy-Olson, Jason Alan Smith, Lily Gladstone, Patrice Fisher, Ryan Begay, Shea Whigham, Tamara Podemski

Director: Erica Tremblay

Rating: R

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, 2024

For the longest time, land was where people formed strength in community, where people were born, lived, died, and was buried in, but it was also how empires grew in power, often at the expense of the people that came before. Exhuma is centered in a haunted burial site of a Korean family that migrated due to the war, but as the shamans try to unearth the casket, they also uncover the psychospiritual ways in which Japan colonized Korea– haunting the land with their own ghosts, dividing its people through belief, and leaving deep scars that hasn’t yet been fully recovered from. While the double exorcism situation can be a tad confusing, Exhuma nonetheless elevates this folk horror drama with their respect and attention to detail for Korean shamanism.

Genre: Horror, Mystery, Thriller

Actor: Baek Seung-chul, Choi Min-sik, Choi Moon-kyoung, Hong Seo-jun, Jang Ui-don, Jeon Jin-gi, Jung Yun-ha, Kim Go-eun, Kim Jae-chul, Kim Ji-an, Kim Min-jun, Kim Sun-young, Kim Tae-jun, Lee Da-wit, Lee Do-hyun, Lee Eun-joo, Lee Jong-goo, Lee Young-lan, Park Jae-wan, Park Jeong-ja, Park Ji-il, Rikiya Koyama, Yoo Hai-jin

Director: Jang Jae-hyun

Rating: NR

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, 2022

It’s a bold move, centering a drama around a creature as docile as a donkey, but EO pulls it off without ever leaning on the crutch of CGI. Instead, the film makes ingenious use of a hundred-year-old film technique: the Kuleshov effect. By splicing the image of the titular donkey’s placid, expressionless face against visual stimulus, the illusion of a genuine reaction is produced.

But don’t be mistaken: this is no twee Disney-esque tale of anthropomorphism. Inspired by the classic Au Hasard Balthasar, EO tracks the haphazard journey of a former circus donkey across Europe — one that is often depicted in surreal psychedelic reds instead of idyllic picture-book tones, and punctured by more horrors than joys (though we do, thankfully, get to see him munch away on some well-deserved carrot treats). EO’s docility frames him as a kind of holy innocent, making the cruelty meted out to him feel all the more like a grave violation of something sacrosanct. Seeing the world through his oft-neglected perspective also makes this a movie about humans by proxy — a fresh, empathetic approach that, even in its obvious dramatic liberties, makes us meditate on both the depth of experience that may be unfolding in our animal neighbors and our role in shaping it.

Genre: Adventure, Drama

Actor: Agata Sasinowska, Anna Rokita, Delfina Wilkońska, Isabelle Huppert, Kateřina Holánová, Lolita Chammah, Lorenzo Zurzolo, Marcin Drabicki, Mateusz Kościukiewicz, Mateusz Murański, Sandra Drzymalska, Tomasz Organek, Waldemar Barwiński

Director: Jerzy Skolimowski

Rating: NR

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, 1991

At first glance, Dogfight seems to be just a standard love story: a Marine falling in love with a woman just before he’s sent overseas. But underneath, there’s a rebuke at American masculinity that needs to be acknowledged. As Eddie and his friends make bets at the expense of their dates, Dogfight rightfully portrays this treatment as casual, unthinking cruelty, and it’s the exact cruelty that they inflict on themselves, the same obedient mindset that continues to push them to various wars around the world at that time. River Phoenix evokes that startling realization with the gentle way Eddie starts to treat Rose, and as the night alternates between his date and the shenanigans his buddies go through without him, Dogfight questions the way boys come of age, this mindset, and what it means to grow up.

Genre: Drama, Romance

Actor: Anthony Clark, Brendan Fraser, Burke Pearson, Christopher Shaw, Elizabeth Daily, Holly Near, Jillian Armenante, John Lacy, Kenneth Utt, Krisha Fairchild, Lili Taylor, Mitchell Whitfield, Peg Phillips, Richard Panebianco, River Phoenix, Robert Munns, Ron Lynch, Sandra Ellis Lafferty, Sue Morales

Director: Nancy Savoca

Rating: R

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, 2020

From the sheer size of Frederick Wiseman's documentaries (both in length and scope), it should be clear that his goal isn't necessarily to have us retain every piece of information he gives us in all of this film's board meetings and press conferences. This is a film interested in the macro view of how a city works, and Wiseman's attention to detail even in his old age (he's 94 at the time of writing this) is truly inspiring for any aspiring documentarian. City Hall doesn't necessarily tell us anything we might not already know about the coordination between a local government unit and its constituents and citizens, but Wiseman gets us to think of the grand design of it all—which is both wondrous and horrifying to behold.

Genre: Documentary

Actor: Marty Walsh

Director: Frederick Wiseman

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, 2019

Due to the possibility of death, Buoyancy cannot be made as a documentary. This film, after all, sheds light on today's real life slavery. But that doesn't mean it's no less true. The script was written based on interviews with real life survivors, who, of course, would rather not be filmed due to their safety. The characters were written to closely reflect them, which was why, even though the studio is Australian, they casted Thai and Cambodian actors, and wrote the dialogue in their respective languages. And the story that writer-director Rodd Rathjen created, gradually escalates the terror Chakra faces on the whims of a cruel captain, with each new experience slowly scrapping off the innocence that was supposed to be protected. Buoyancy is not a documentary, but it works as a necessary exposé of slavery in Southeast Asian seas because of Rathjen sticking true to the sadly real life atrocity.

Genre: Crime, Drama

Actor: Rous Mony, Saichia Wongwirot, Sarm Heng, Thanawut Ketsaro, Yothin Udomsanti

Director: Rodd Rathjen

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