497 Best Challenging Movies to Watch (Page 12)

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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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, 2022

In 1994, Danish auteur Lars von Trier came up with a TV series called The Kingdom, an absurd supernatural comedy that takes place in a rundown hospital in Copenhagen. The show was well-received enough to warrant a second season, but just as von Trier was polishing up the third and final installment, the deaths of more than one lead actor pressed pause on the project, till now.

More than 10 years in the making, The Kingdom part III, also called Exodus, is still very much centered on the weird patients and staff members that populate the Riget hospital, as well as the possible evil buried beneath it. The comedy/horror has a robot dishwasher and a giant head. Danes and Swedes are perennially at war with each other. Willem Dafoe and Alexander Skarsgard make odd cameos.

I’m not sure it’s possible to write a coherent synopsis without sounding like I’ve fallen off the rails, but know that it is a unique headscratcher of a show, more interesting as an experience than anything else. Von Trier was also openly inspired by Twin Peaks, in making it, so David Lynch fans in particular will truly enjoy diving into this world.

Genre: Comedy, Drama, Fantasy, Horror, Mystery, Thriller, TV Movie

Actor: Annevig Schelde Ebbe, Baard Owe, Benny Hansen, Benny Poulsen, Birgitte Raaberg, Birte Tove, Claus Nissen, Claus Strandberg, Danica Curcic, Dick Kaysø, Else Petersen, Erik Wedersøe, Ernst-Hugo Järegård, Finn Nielsen, Ghita Nørby, Gordon Kennedy, Helle Virkner, Henning Jensen, Henrik Koefoed, Holger Juul Hansen, Holger Perfort, Jens Okking, Julie Wieth, Kirsten Rolffes, Kurt Ravn, Lars Lunøe, Lars von Trier, Laura Christensen, Lene Vasegaard, Lise Schrøder, Mette Marckmann, Mette Munk Plum, Michael Moritzen, Morten Eisner, Nis Bank-Mikkelsen, Ole Boisen, Ole Dupont, Otto Brandenburg, Paul Hüttel, Peter Gilsfort, Peter Mygind, Solbjørg Højfeldt, Solveig Sundborg, Søren Elung Jensen, Søren Hauch-Fausbøll, Søren Pilmark, Søren Steen, Svend Ali Hamann, Thomas Bo Larsen, Tove Maës, Udo Kier, Ulrik Cold, Vic Carmen Sonne, Vita Jensen, Willem Dafoe

Director: Lars von Trier, Morten Arnfred

Rating: TV-MA

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, 1989

There’s something wrong with the Le Hollandais restaurant in London where most of the events of The Cook, the Thief, His Wife & Her Lover. When the mobster makes the sudden decision to venture into restaurant acquisition, this high class French restaurant is turned upside down, with his hot-tempered, cruel behavior so over-the-top, unnecessary, and violent that his wife’s sexual affair actually feels rather tame, and yet silently rebellious. This story is quite straightforward for director Peter Greenaway, but in his hands, the melodrama becomes highly stylized, with separate rooms assigned colors, with the dishwasher singing classical opera, and with sharp observation of how much is lost when those with money can take over at the expense of the artisans, the scholars, and those more vulnerable in society.

Genre: Crime, Drama

Actor: Alan Howard, Alex Kingston, Ciarán Hinds, Diane Langton, Emer Gillespie, Ewan Stewart, Gary Olsen, Helen Mirren, Ian Dury, Ian Sears, Janet Henfrey, Liz Smith, Michael Gambon, Paul Russell, Richard Bohringer, Roger Ashton-Griffiths, Roger Lloyd Pack, Ron Cook, Sue Maund, Tim Roth, Tony Alleff, Willie Ross, Yolande Brener

Director: Peter Greenaway

Rating: R

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, 2017

This fiery coming-of-age drama has an unlikely origin story: director Jonas Carpignano was first introduced to the sprawling Roma clan that makes up most of the movie’s cast when one of them stole his car while he shot another film. The charismatic Amato family made such an impression on him that he decided to center a movie around their real lives, naming it for the insular neighborhood they live in on the outskirts of a Southern Italian town.

The Amatos are part of a much-maligned ethnic minority, but not the only one in the film. The Ciambra pokes at the idea of solidarity between the Amatos and local African migrants: while his elders are quick to reject the idea, plucky 14-year-old Pio (Pio Amato) flits across these invisible borders and bonds with Ayiva (Koudous Seihon). But Pio is desperate to win the respect of the men in his family, who might then allow him to take part in their criminal exploits — a crisis point The Ciambra chronicles with raw emotion. This is a movie whose grit and bleakness often recall the uncompromising gaze of neo-realist classics, as a child is heartbreakingly forced to declare his allegiances in the dog-eat-dog world his elders can’t imagine an alternative to.

Genre: Crime, Drama

Actor: Damiano Amato, Francesco Papasergio, Iolanda Amato, Koudous Seihon, Patrizia Amato, Pio Amato, Rocco Amato, Susanna Amato, Swamy Rotolo

Director: Jonas Carpignano

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, 2023

Since we live in a society, interacting with authority is inescapable. Terrestrial Verses depict fairly mundane day-to-day interactions– getting a birth certificate, settling a traffic violation, or attending a job interview– but through nine vignettes framed with a static camera, aimed at a person trying to negotiate with someone more powerful just outside the frame, these mundane interactions become satirically absurd. For those unfamiliar with the ideology behind the regime, these interactions are just so annoying. But for those in the know, the doublespeak in the dialogue reflects how finicky and arbitrary the rules set by the authoritarian regime are, and celebrates the wit and ingenuity of the ordinary people that have to navigate them. Terrestrial Verses seems utterly mundane at first, but it proves to be smart, incisive, and deeply insightful.

Genre: Comedy, Drama

Actor: Babak Karimi, Farzin Mohades, Gohar Kheyrandish, Hossein Soleymani, Majid Salehi, Reza Behboudi, Sadaf Asgari, Sara Bahrami

Director: Ali Asgari, Alireza Khatami

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, 2022

Stutz is Jonah Hill’s loving tribute to his therapist Phil Stutz, a smart and empathetic man who’s dedicated his entire life to helping people. The conversations between them, deeply personal and vulnerable, are meaningful in themselves, but Stutz also works as a helpful instruction on how to be your best self and as a metanarrative on telling honest stories on a medium as seemingly artificial as film (it is similar to Bo Burnham’s Inside in that way).

Stutz is at once experimental and comforting, a real gem especially for people with an interest in psychoanalysis and alternative psychiatry. It’s at its best when the two men deal with uncomfortable truths in the kindest of ways, and it's sure to be something people will return to often for advice and solace. Fun fact: the documentary was co-produced by Joaquin Phoenix and Rooney Mara.

Genre: Documentary, Drama

Actor: Jonah Hill

Director: Jonah Hill

Rating: R

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, 1994

Prepare to be captivated by the bittersweet tale of Strawberry and Chocolate, a 1994 Cuban film that immerses you in the complexities of friendship, love, and societal taboos. Set against the backdrop of Havana, the movie beautifully explores the relationship between an earnest university student and a sophisticated gay artist. With its poignant storytelling engrossing itself in the socio-political climate of Cuba, the film delves into themes of identity, acceptance, and the clash between tradition and individuality. Powerful and emotionally resonant, the vibrant Cuban culture is expertly woven into the narrative, transporting you to the heart of Havana's vibrant streets. 

Genre: Comedy, Drama

Actor: Francisco Gattorno, Jorge Perugorría, Mirta Ibarra, Vladimir Cruz

Director: Juan Carlos Tabío, Tomás Gutiérrez Alea

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, 1988

Based on the true story of the last French woman executed by guillotine, Story of Women depicts wartime survival under the Vichy regime. While men were sent to fight in the war, women in France stayed home, in a country occupied by the Nazis, with their government collaborating with the Axis powers they were supposedly at war with. Marie-Louise Giraud is one such woman. Like her country, she is pushed to do crimes forbidden by the state, first for kindness, but eventually for comfort, but only she gets the death penalty for 27 abortions, when only a few Vichy officials have been tried for crimes against humanity, which includes the deportation of seventy thousand Jews to concentration camps. The contrast is made much more poignant with Isabelle Huppert and Claude Chabrol’s creative partnership.

Genre: Drama

Actor: Caroline Berg, Dani, Dominique Blanc, Evelyne Didi, Franck de la Personne, François Cluzet, François Maistre, Guillaume Foutrier, Henri Attal, Isabelle Huppert, Jacques Brunet, Jean-Michel Noirey, Lolita Chammah, Marie Bunel, Marie Trintignant, Nils Tavernier, Pierre-François Dumeniaud, Sylvie Flepp, Vincent Gauthier

Director: Claude Chabrol

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, 2017

Another indie zombie movie? Far from it. One Cut of the Dead, written and directed by Shin'ichirô Ueda, became a global sensation following its small theatrical run in Japan for its creative and original screenplay. A hack director and film crew are shooting a low-budget zombie movie in an abandoned WWII Japanese facility when they are attacked by real zombies. That’s all you need to know about the plot, as the film is full of surprises that will catch you off guard. Wondering how an independent film with a budget of just $25,000 was able to gross over $30 million worldwide? The answer lies in the film itself. 

Genre: Comedy, Drama, Horror

Actor: Ayana Goda, Donguri, Harumi Shuhama, Harumi Syuhama, Hiroshi Ichihara, Kazuaki Nagaya, Manabu Hosoi, Mao, Miki Yoshida, Sakina Asamori, Shinichiro Osawa, Shiori Nukumi, Shuntaro Yamazaki, Takayuki Hamatsu, Tomokazu Yamaguchi, Yuzuki Akiyama

Director: Shin'ichirō Ueda, Shin'ichiro Ueda

Rating: Not Rated, Unrated

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, 2023

While not its only cause, the increase of conflict and civil wars has spurred a global refugee crisis. Millions of refugees have been displaced from their homes, taking dangerous journeys to a hopefully safer place. Nowhere, now on Netflix, showcases one possible journey. Escaping a future totalitarian Spain, the film is centered on leading lady Anna Castillo, whose excellent performance pulls most of the tears here. With her character Mia’s ingenuity, she maximizes her shipping container’s resources and takes steps to ensure her survival. While some of the backstory can feel thin, after all, for most of the runtime Mia has only herself to talk to, this new one-location survival film is a thrilling addition to the genre. It’s a chilling reminder of what could be happening to the millions of refugees seeking safe haven around the globe.

Genre: Drama, Thriller

Actor: Anna Castillo, Antonio Buíl, Edu Bulnes, Emma Sánchez, Irina Bravo, Kaabil Sekali, Lucia Soria, Mariam Torres, Mary Ruiz, Said El Mouden, Tamar Novas, Tony Corvillo, Victoria Teijeiro

Director: Albert Pintó

Rating: R

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, 2003

Monster is a biographical depiction of Aileen Wuornos (Charlize Theron), a prostitute and serial killer who murdered seven men in Florida between 1989 and 1990. The film follows the burgeoning relationship between Wuornos and young Selby Wall (Christina Ricci, in a role based on Wuornos' real-life girlfriend Tyria Moore), as she grows increasingly desperate to provide for her young companion financially. Her desperation and her rage against men, brought on by years of both childhood and adult abuse, leads her down a dark path of murder and theft, even as she struggles to shield Selby from the horror of her crimes. The overwhelming highlight of the film is Theron’s mesmerizing performance as Wuornos—a role that won her a well-deserved Academy Award for Best Actress in 2004. She’s almost unrecognizable and altogether phenomenal as the volatile and increasingly unstable Wuornos, whose ferocity is interwoven with surprising affection for young Selby. This unexpected tenderness lends the film an air of tragic poignancy, and provides a bittersweet portrayal of a severely troubled woman. Very much intended for mature audiences only, Monster is a fascinating recreation of a disturbing yet compelling chapter in the annals of true crime in America.

Genre: Crime, Drama

Actor: Al, Annie Corley, Brett Rice, Bruce Dern, Bubba Baker, Cannonball, Catherine Mangan, Charlize Theron, Christian Stokes, Christina Ricci, Cree Ivey, Glenn R. Wilder, Jesse Stern, Jim R. Coleman, Kaitlin Riley, Kane Hodder, Lee Tergesen, Lyllian Barcaski, Magdalena Manville, Marc Macaulay, Marco St. John, Pruitt Taylor Vince, Romonda Shaver, Rus Blackwell, Scott Wilson, Stephan Jones, Tim Ware

Director: Patty Jenkins

Rating: R

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, 2019

You may have heard about this 2019 critic-favorite from clips like this one of a kid running to flee the movie theater during a screening. “little billy ran the f**k out the door”, the caption reads.

You will want to do the same. Recovering from losing her sister and her parents in a single incident, a young girl goes on a trip to Sweden to observe a ritual within a bizarre commune that occurs every 90 years. This cult’s idea of death and their traditions intersect with the girl’s grief to create unthinkable monstrosities.

Note: while some readers praise the movie for its depiction of anxiety, I highly recommend against watching Midsommar if you suffer from panic attacks.

Genre: Drama, Horror, Mystery

Actor: Agnes Westerlund Rase, Anders Back, Anders Beckman, Anki Larsson, Anna Åström, Anna Berentzen, Archie Madekwe, Ari Aster, Austin R. Grant, Björn Andrésen, Ellora Torchia, Florence Pugh, Frans Cavallin Rosengarten, Gunnel Fred, Hampus Hallberg, Henrik Norlen, Isabelle Grill, Jack Reynor, Julia Ragnarsson, Katarina Weidhagen, Klaudia Csányi, Lars Väringer, Lennart R. Svensson, Levente Puczkó-Smith, Liv Mjönes, Louise Peterhoff, Mats Blomgren, Mihály Kaszás, Rebecka Johnston, Tove Skeidsvoll, Vilhelm Blomgren, Vilmos Kolba, Will Poulter, William Jackson Harper, Zsolt Bojári

Director: Ari Aster

Rating: R

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, 2020

Rather than talking about what it takes to get to the other side of the border, Identifying Features instead focuses its attention back home. It’s part of the reason why the film actually highlights how difficult this actually is– Before even reaching it, people hoping to enter America go through a dangerous journey, many of whom disappear without any resolution for the loved ones left behind. But in focusing on what happens back behind the border, the social issue drama becomes more compelling, as the mystery of what happened to the son that left easily strikes a cord and drives the plot forward rather than straightforwardly talking about the journey. As she does so, writer-director Fernanda Valadez sets a spine-tingling mood, with striking, cryptic shots paired with the sober, difficult explanations the loved one who have been left behind with her have tried to formulate. Sin Señas Particulares captures that painful story in such a bold and thoughtful debut.

Genre: Drama

Actor: Ana Lauda Rodríguez, Armando García, David Illescas, Juan Jesús Varela, Mercedes Hernández

Director: Fernanda Valadez

Rating: NR

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, 2015

Heart Attack is a romantic comedy, but instead of the hijinks being caused by the usual dating, miscommunication, and wooing, Yoon’s struggle here is to finally get a hold of his overbearing schedule and figure out how to relax and recover from burnout, and it’s all inspired by wanting to impress his doctor Imm. It’s funny, but it’s also all too real. Writer-director Nawapol Thamrongrattanarit recreates the overwhelming frenzy to complete a job through a magnificent jazz soundscape and Sunny Suwanmethanon’s internalized monologue, and it’s such an effective cinematic translation that the moments of rest, the moments where Yoon and Imm finally take a break feels like a relief. Heart Attack works precisely because it empathizes and understands the experience of workers in today’s gig economy.

Genre: Comedy, Drama, Romance

Actor: Adisorn Trisirikasem, Banjong Pisanthanakun, Chatcharin Saetan, Chonlasit Upanigkit, Davika Hoorne, Morakot Liu, Natda Chawawanid, Nottapon Boonprakob, Panjavit Tangtongjit, Sunny Suwanmethanon, Sunny Suwanmethanont, Surattanavee Suviporn, Surattanawee Suviporn, Thanapob Leeratanakachorn, Tor Thanapob Leeratanakachorn, Torpong Chantabubpha, Vichai Matakul, Violette Wautier

Director: Nawapol Thamrongrattanarit

Rating: N/A

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