473 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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, 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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, 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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, 2024

Are connections truly fated, completely chosen, or purely circumstantial? The slow tragedy of Henry James’ The Beast in the Jungle hangs entirely on the question, which captivated readers and filmmakers with the concept, including Bertrand Bonello, which forms the foundations of 2023’s The Beast. Bonello lets loose The Beast in the Jungle into an AI playbox of time and space and destiny, transforming the simple examination of human life into a sci-fi epic, a moving period romance, and an existential mystery all at once. It can occasionally feel a bit jumbled up at times, with the way Bonello jumps across lives, but Léa Seydoux and George MacKay hold everything together with their performance, making La Bête deeply striking, if a bit derivative.

Genre: Drama, Romance, Science Fiction

Actor: Bertrand Bonello, Dasha Nekrasova, Elina Löwensohn, George MacKay, Guslagie Malanda, Julia Faure, Laurent Lacotte, Léa Seydoux, Marta Hoskins, Martin Scali, Xavier Dolan

Director: Bertrand Bonello

Rating: NR

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, 2023

If you’re hard working and well-situated enough, you get to chase and achieve and live out your dreams for your whole life. But if you’re lucky enough, you get to choose how you’ll leave. Swan Song is the journey Canadian ballet icon Karen Kain took to direct one last production of Swan Lake just before retiring as artistic director of National Ballet of Canada. Director Chelsea McMullan takes a fairly standard approach in her documentary, but to be fair, the subject matter is interesting by itself. The beauty of the ballet has long captivated cinema, so it’s unsurprising that the beauty is present, but McMullan effortlessly highlights the way Kain shaped her directorial style based on her own experience, with more humane and collaborative leadership that allowed the country’s troupe to shine.

Genre: Documentary

Actor: Jurgita Dronina, Karen Kain, Shaelynn Estrada, Siphesihle November

Director: Chelsea McMullan

Rating: NR

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, 2023

There are some connections that transcend definition, becoming more important and fundamental to one’s life than that of a romantic relationship. Not many people are lucky to have experienced it, but nevertheless it’s true. Soulmate is the Korean adaptation of the 2016 Chinese directorial debut, and while it’s faithful to the source material, there’s a focus to this rendition that elevates the film, with a greater emphasis on the titular soulmates rather than the boy that tore them apart. Because of this, Soulmate is much more emotionally devastating, neatly shifting some character revelations in order to grant the weight each moment deserves.

Genre: Drama, Romance

Actor: Byeon Woo-seok, Heo Ji-na, Hyun Bong-sik, Jang Hye-jin, Jeon So-nee, Kang Mal-geum, Kim Da-mi, Lee Suk-hyeong, Nam Yoon-su, Oh Min-ae, Park Choong-seon, Park Seong-yeon

Director: Min Yong-keun

Rating: NR

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, 1993

Generally, a mentorship is a great way to find guidance and direction, but rarely do we discuss the importance of finding the right mentor– or the right mentors– and that it sometimes takes a while to find a great fit. Searching for Bobby Fischer is about real-life child chess prodigy Josh Waitzkin, but rather than depicting the straightforward mentorship plot we’ve seen in many sports films before, the film captures the journey of a boy who needs both the freedom and the structure for his chess career. Searching for Bobby Fischer does take on the tone and style typical of these child prodigy biopics, but Waitzkin’s story is worth telling, especially for children trying to find their own voice outside of their guardians.

Genre: Drama

Actor: Andrew Sardella, Anthony Heald, Austin Pendleton, Ben Kingsley, Bobby Fischer, Caroline Yeager, Chelsea Moore, Dan Hedaya, David Paymer, Hal Scardino, Joan Allen, Joe Mantegna, John Bourgeois, Josh Kornbluth, Josh Mostel, Laura Linney, Laurence Fishburne, Maria Ricossa, Max Pomeranc, Michael Nirenberg, Nathan Carter, R.D. Reid, Robert Stephens, Steven Randazzo, Tom McGowan, Tony De Santis, Tony Shalhoub, Vasek Simek, William Colgate, William H. Macy

Director: Steven Zaillian

Rating: PG

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, 1989

With an acrobat in a sanitarium, elephant trunks spouting blood, and a religious cult whose patron saint is a rape victim, Santa Sangre isn’t going to be an easy watch, especially with the avant-garde direction of the iconic Alejandro Jodorowsky. It’s tough to watch the explicit scenes, both of Fenix’s childhood circus reality and his adult hallucinations, with the hallucinations visually recalling his childhood trauma. But through these terrifying, freaky images, Jodorowsky takes his own memories and crafts it into a twisted, but deeply personal psychosexual nightmare, confronting the exploitative nature of faith and family through various circus acts. Santa Sangre is one of its kind.

Genre: Drama, Horror, Thriller

Actor: Adan Jodorowsky, Axel Jodorowsky, Blanca Guerra, Brontis Jodorowsky, Faviola Elenka Tapia, Gloria Contreras, Gustavo Aguilar Tejada, Guy Stockwell, Héctor Ortega, Hilario 'Popitekus' Vargas, Jacobo Lieberman, Jesús Juárez, Joaquín García Vargas, Sabrina Dennison, Sergio Bustamante, Teo Jodorowsky, Teo Tapia, Thelma Tixou, Valérie Crouzet, Zonia Rangel Mora

Director: Alejandro Jodorowsky

Rating: NC-17

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, 1993

While most are familiar with Hollywood depictions of the transatlantic slave trade, there were also other countries that depicted this terrible time period, including countries from the African continent. Ethiopian filmmaker Haile Gerima self-funded and self-distributed Sankofa in its initial release, but despite the lack of screens, it still managed to become a landmark classic thankfully restored. Like plenty of films on the topic, Gerima creates a harrowing depiction of the slave owners’ evil, but unlike others, it’s more interested in the difficult dynamics between the enslaved, the ways they sought refuge and freedom in each other, and the inner lives of the community they shared despite the terror, all through Gerima’s striking images and the masterfully mixed soundscape, both in the soundtrack and various accents. It’s not perfect, and it’s definitely not easy to watch, but Sankofa has a distinct vision that needs to be seen.

Genre: Drama, Fantasy, History, Science Fiction

Actor: Afemo Omilami, Alexandra Duah, Kofi Ghanaba, Mutabaruka, Mzuri, Nick Medley, Oyafunmike Ogunlano, Reggie Carter, Reginald Carter

Director: Haile Gerima

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Shot from the movie

, 1990

This gripping legal drama is based on a case we still don’t know the truth of — which might make it seem like a pointless exercise, were it not for the fact that it’s infectiously fascinated by greater questions than whether wealthy socialite Claus von Bülow (Jeremy Irons) really did attempt to kill wife Sunny (Glenn Close), who was left comatose by the mysterious event. After being convicted, Claus recruited for his appeal then-hotshot lawyer Alan Dershowitz (Ron Silver), now better known for personal allegations and his defense of men even more nefarious than Claus. Reversal follows the tricky legal argument-crafting process, embedding us with Dershowitz’s elite team as they meticulously comb through the prosecution’s theory to find the hairline crack they need to break the case open.

But why go to all this effort to exonerate an unlikeable and frustratingly enigmatic man like Claus, whom Dershowitz apparently doesn’t even believe himself? While we’re morbidly fascinated by unknowable cases like this, it’s the passion of the defense that’s really puzzling — something Reversal shrewdly gets as it wrestles with the ethical arguments for and against Dershowitz’s involvement, making for a pre-courtroom drama whose power extends beyond that of the particular case it documents.

Genre: Drama

Actor: Alan Pottinger, Annabella Sciorra, Bill Camp, Brian Delate, Bruno Eyron, Christine Baranski, Christine Dunford, Constance Shulman, Edwin McDonough, Ericka Klein, Felicity Huffman, Fisher Stevens, Frank Stellato, Frederick Neumann, Glenn Close, Gordon Joseph Weiss, Jack Gilpin, Jad Mager, JD Cullum, Jeremy Irons, Jessika Cardinahl, Johann Carlo, Julie Hagerty, Keith Reddin, Larry Sherman, Leo Leyden, LisaGay Hamilton, Malachy McCourt, Mitchell Whitfield, Redman Maxfield, Ron Silver, Sarah Fearon, Stephen Mailer, Tom Wright, Uta Hagen

Director: Barbet Schroeder

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