497 Best Challenging Movies to Watch (Page 28)

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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406. Night Sky, 2022

Night Sky has an intriguing premise—underground, an elderly couple visits a portal to another world, while aboveground they go through the trials and tribulations of marriage and old age. You would think that the sci-fi element would overpower everything else in this story, but on the contrary, it’s the slice-of-life chemistry between Franklin and Irene York (played by Oscar winners JK Simmons and Sissy Spacek, respectively) that truly grounds the out-of-this-world series. Watching them pull from impressive depths and deliver consistent performances compensates for the slower and confusing plot lines in the show. Tune in for the dazzling mystery below their shed, the titular night sky that reveals evolving puzzles, but stay for the performances—grounded, honest, and ever-so gripping.

Genre: Drama, Sci-Fi & Fantasy, Science Fiction

Actor: Adam Bartley, Cass Buggé, Chai Hansen, J.K. Simmons, Julieta Zylberberg, Kiah McKirnan, Rocío Hernández, Sissy Spacek

Rating: TV-14

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407. Naked, 1993

	
It doesn’t matter how many years have passed, Naked is the kind of film that’s sure to shock you with its wit and violence. There’s no plot, really, but we do follow Johnny (an explosive David Thewlis) as he drifts around London, announcing doomsday prophecies, conspiracy theories, and philosophical observations about the world. The thing is, unlike your usual street weirdo, Johnny is actually intelligent, eloquent, and dangerously charming. His forceful presence has varying effects on people, who are all bruised but undoubtedly affected by him. One of them is a hopeful nightguard, the other is a depressed waitress. He also meets homeless immigrants and a punk. They’re cynical and angry like Johnny (they make up the city's underbelly after all) but unlike them, Johnny expresses all that he thinks and feels, even if those words just mask the fear and insecurity that’s eating him up inside. Naked angered a lot of people when it first came out in 1993, but its unfiltered portrait of the neglected sectors in Britain is sure to have the same dizzying effect on viewers today.Genre: Comedy, Drama
Actor: Angela Curran, Claire Skinner, David Thewlis, Elizabeth Berrington, Ewen Bremner, Gina McKee, Greg Cruttwell, Katrin Cartlidge, Lesley Sharp, Peter Wight, Sandra Voe, Susan Vidler, Toby Jones
Director: Mike Leigh
Rating: NR

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408. My First Film, 2024

	
Aspiring writer-director Vita of My First Film is insufferable. When she starts out making her first feature, she’s pleasantly surprised by the people who came to help her, but the repetition of the shoot, the scene not matching the idea in her head, which she tries to put into image and word, but can’t quite make the vision clear, the anxiety and pressure to be a professional filmmaker blinding her from the concerns of her cast and crew all combine to an inevitable failure of her first feature, which also happens to inspired by Vita’s actual life. Vita is insufferable, but writer-director Zia Anger manages to make her real in an eclectic meta multimedia patchwork that won’t work for everyone, but uniquely depicts an experience filmmakers, aspiring or otherwise, haven’t wanted to talk about.Genre: Drama
Actor: Cole Doman, Devon Ross, Eamon Farren, Eléonore Hendricks, Jane Wickline, Joanna Fang, Odessa Young, Philip Ettinger, Sage Ftacek, Zia Anger
Director: Zia Anger

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409. Mississippi Damned, 2009

In Tina Mabry’s first full length feature film Mississippi Damned she tells the story of three poor, Black adolescents as they advance into adulthood. The story is mostly centered on Kari Peterson, portrayed by Tessa Thompson, who has fallen witness and victim to violence/abuse since her childhood. As she navigates her trauma while facing poverty and familial issues, we begin to understand the inner machinations of Kari and those who have harmed her.

While Mississippi Damned isn’t particularly easy to digest, I consider it essential. As unflinchingly brutal as this film is, it taught me a lot about trauma and how to navigate my own. With performances as powerful as these, it’s impossible to forget this film.

Genre: Drama

Actor: Adam Clark, Cynthia Addai-Robinson, D.B. Woodside, Malcolm David Kelley, Malcolm Goodwin, Michael Hyatt, Simbi Khali, Tessa Thompson

Director: Tina Mabry

Rating: TV-MA

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410. Miracle in Cell No. 7, 2013

	
Sometimes it's hard to relate to foreign movies because of the different cultures, languages and actors. But Miracle in Cell No. 7 transcended the language barriers for me and delivered one of the most touching stories I have ever seen. It's a Korean film about the intricate yet simple love story between a mentally challenged father and his daughter. When the father is wrongly accused of a crime he did not commit and is sent to prison, his personable character eventually causes the prisoners around him to help reunite him with his daughter in prison. Warning: many tissues will be needed.Genre: Comedy, Drama, Family
Actor: Choi Ro-woon, Dal-su Oh, Gal So-won, Han Yi-jin, Im Jae-min, Jeong Man-sik, Jin-young Jung, Jo Deok-hyeon, Jo Jae-yoon, Jo Jae-yun, Jung Han-bi, Jung Hee-tae, Jung Jin-young, Jung Man-sik, Jung-tae Kim, Kal So-won, Kang Seung-wan, Kang Ye-seo, Kim Jung-tae, Kim Ki-cheon, Kim Ki-chun, Kim Se-dong, Kyul Hwi, Lee Seung-yeon, Lee Yoon-hee, Man-shik Jeong, Man-sik Jeong, No Kang-min, Oh Chang-kyung, Oh Dal-su, Park Gil-su, Park Kil-soo, Park Sang-myeon, Park Shin-hye, Park Won-sang, Ryu Seung-ryong, Seung-ryong Ryu, Shin-Hye Park, So Won Kal, Song Lee-woo, Won-sang Park, Yeo Moo-yeong, Yeseo, Yoon Sun-Woo
Director: Hwan-kyung Lee, Lee Hwan-kyung
Rating: N/A, Not Rated

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411. Metallic Rouge, 2024

With most of early January 2024’s slate focused on fantasy, Metallic Rouge is a fairly decent cyberpunk refresher. With fantastic, mostly 2D animation, studio Bones’ 25th Anniversary project has spectacular mecha match-ups between government android Rouge Redstar versus various members of the excellently designed Immortal Nine, as well as humorous, expository banter from Rouge’s human partner Naomi Orthmann. But it’s the mystery that drives interest in the show, as Nean androids and humans share a world, but not the same status, and the origins of the artificial intelligence bots seem to link with a previous alien invasion that pushed humanity into further space exploration. It’s an interesting premise, and the structure is definitely unusual, but with Bones’ track record, we’re expecting that it’ll all come together by the end of Metallic Rouge.

Genre: Action & Adventure, Animation, Sci-Fi & Fantasy

Actor: Atsushi Miyauchi, Chiaki Kobayashi, Hiroyuki Yoshino, Kazuyuki Okitsu, Kenjiro Tsuda, Shunsuke Takeuchi, Tomoyo Kurosawa, Yu Shimamura, Yui Ogura, Yume Miyamoto

Director: Yutaka Izubuchi

Rating: TV-14

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412. Martin Eden, 2019

Loosely based on the 1909 novel, Martin Eden is a stunning film about the hollow success of individualism. The plot points remain the same: Eden, a self-taught sailor, wants to win the heart of the wealthy Elena Orsini. To do this, he strives to break into the upper class with his writing. However, in this film, writer-director Pietro Marcello adds another dimension to the anti-individualist story: he transports Eden from his original California setting to Naples—allowing for views of different cultures, languages, and classes. By intercutting between old film stock and lingering close-ups, Marcello draws from his documentary background to masterfully evokes the process of remembering. And in refusing to define the time period, Marcello recognizes that Eden's struggle is still ongoing today—and that his success is still hollow.

Genre: Drama, Romance

Actor: Aniello Arena, Anna Patierno, Autilia Ranieri, Carlo Cecchi, Carmen Pommella, Chiara Francini, Denise Sardisco, Edoardo Sorgente, Elisabetta Valgoi, Franco Pinelli, Gaetano Bruno, Giustiniano Alpi, Jessica Cressy, Lana Vlady, Luca Marinelli, Marco Leonardi, Maurizio Donadoni, Pietro Ragusa, Rinat Khismatouline, Sergio Longobardi, Vincenza Modica, Vincenzo Nemolato

Director: Pietro Marcello

Rating: TV-PG

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413. Letter from Masanjia, 2019

	
When thinking about buying something, it’s easy to only think about price and quality, but with many investigations around the world about inhumane labor practices, it’s no wonder that more people would like to look at the companies they’re buying from, or at least buy secondhand when possible. One such investigation is depicted in Letter from Masanjia. While it starts first at the discovery of the letter in Oregon, the true story continues on the other side of the world, through the difficult experiences Sun Yi and his fellow detainees were forced to go through when the Falun Gong movement grew greater in number than the Chinese Communist Party. It’s a harrowing tale, with certain sequences being animated due to a natural lack of footage, and it’s one that needed to be made.Genre: Documentary
Actor: Fu Ning, Julie Keith, Sun Yi
Director: Leon Lee

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414. Lawn Dogs, 1997

	
Adults and kids can be friends, but there’s obviously a line that shouldn’t be crossed. This line is why most people would look at a friendship like this and automatically assume terrible things, but Lawn Dogs depicts one such connection in such a way that it’s clear how easy and disproportionate these assumptions are made for marginalized and less powerful people, over the affluent sociopaths that can and have gotten away with the accusations they lobby against others. The fairy tale ending, and of course, the disgusting behavior done by the rich guys, might turn some viewers off from the movie, but there’s also something genuine with the way screenwriter Naomi Wallace depicts a girl with a literally different heart who just wants to befriend someone real.Genre: Drama
Actor: Angie Harmon, Beth Grant, Bruce McGill, Christopher McDonald, David Barry Gray, Eric Mabius, Kathleen Quinlan, Miles Meehan, Mischa Barton, Sam Rockwell, Tom Aldredge
Director: John Duigan
Rating: R

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415. Khufiya, 2023

If you’re looking for exotic locations, glamorous spies, and dramatic shoot-outs, Khufiya is not the espionage film you’re looking for. Like the original novel it’s based on, the film adaptation is a complex, intricate spy story where countries try to interfere with each other’s affairs, and agents handle the dry and dirty work to achieve this. With the true-story-based details of the source material, writer-director Vishal Bhardwaj keeps the story’s historical accuracy, but also adds a personal revenge subplot through the addition of a female main protagonist. The result of the changes complicates the film’s introduction, but if you have the patience, Khufiya still has what makes a spy drama compelling– the double-agent turns, the doubts and mistrust, and a satisfying resolution to the operation.

Genre: Crime, Mystery, Thriller

Actor: Alexx O'Nell, Ali Fazal, Ashish Vidhyarthi, Atul Kulkarni, Azmeri Haque Badhon, Disney James, Jan Graveson, Lalit Parimoo, Navnindra Behl, Priyanka Setia, Purnendu Bhattacharya, Rahul Vohra, Shashi Bhushan, Shataf Figar, Tabu, Wamiqa Gabbi

Director: Vishal Bhardwaj

Rating: R

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416. Involuntary, 2008

	
Anthology films are interesting because it’s not just one film on screen– it’s multiple stories, one after the other, that might have different plots, but share similar themes, ideas, and styles that the filmmaker(/s) would like to display. Involuntary does have five separate short films, but rather than play one by one, writer-director Ruben Östlund chops them up and alternates between them, starting with small instances where the group pushes someone into a behavior, then eventually escalating and accelerating into much more difficult consequences. This makes for a very slow start to the one and a half hour film, but it also allows Östlund some scope, with this simple group dynamic directly affecting larger ideas such as public morality, masculinity, and high-risk behavior in teens amongst others.Genre: Comedy, Drama
Actor: Cecilia Milocco, Henrik Vikman, Leif Edlund, Leif Ericson, Linnea Cart-Lamy, Lola Ewerlund, Maria Lundqvist, Olle Liljas, Sara Eriksson, Simeon Nordius, Vera Vitali, Villmar Björkman
Director: Ruben Östlund

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417. If These Walls Could Talk, 1996

	
You would think that a film made with Demi Moore, Sissy Spacek and Cher would be a major theatrical release, but even in 1996, the topic of abortion rights was still quite controversial. If These Walls Could Talk may be relegated to the small screen because of this, or because of being an anthology of shorts, but with each lead starring each segment, the film outlines real experiences with abortion, from the dangerous ways women had to resort to without it, to the way, that even with the Court’s support, these rights were actively suppressed. Of course, it’s a harrowing, unsubtle watch, and it would have been great to have a segment depicting the safety of modern day procedures, but if you have a friend that’s unconvinced of the procedure’s necessity, or if they’re entirely new to the conversation, If These Walls Could Talk is a place to start.Genre: Drama, TV Movie
Actor: Aaron James Cash, Aaron Lustig, Anne Heche, Ben Marley, Brendan Ford, Carmen Thomas, Catherine Keener, CCH Pounder, Cher, Chris Ellis, Christine Avila, Craig T. Nelson, Demi Moore, Diana Scarwid, Eileen Brennan, Geoffrey Nauffts, Georganne LaPiere, Harris Yulin, Hedy Burress, Ian Bohen, Jack Kehler, Jada Pinkett Smith, Janna Michaels, Jason London, Joanna Gleason, Jordana Spiro, Judith Drake, Kevin Cooney, Lindsay Crouse, Lorna Scott, Lorraine Toussaint, Mary Portser, Matthew Lillard, Phyllis Lyons, Rita Wilson, Rob Camilletti, Robert Wisdom, Robin Gammell, Rusty Schwimmer, Sally Murphy, Sarah Koskoff, Shirley Knight, Sissy Spacek, Susie Spear Purcell, Tim DeKay, Vaughn Armstrong, Xander Berkeley, Zack Eginton
Director: Cher,  Nancy Savoca
Rating: R

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418. Idiots and Angels, 2008

	
As much as we’d like to think everyone can be redeemed, there are terrible, awful people that do exist that make it hard to believe in change. Idiots and Angels takes one such person named Angel, and forces him through a highly unusual, creepy, and cynical redemption tale that involves a body transformation that’s less heavenly and more Kafkaesque. As he pulls feathers from his body, Angel’s miserable, terrible self has no choice but to act decently for once. It’s a unique transformation, one we wish our curmudgeonly acquaintances would have, and with no words spoken, Bill Plympton’s unique cross-hatched animation takes center stage. Idiots and Angels may not be the most perfect animated film out there, but it’s certainly one of its kind, something you’ve probably never seen before.Genre: Animation, Comedy, Drama, Fantasy
Actor: Arielle Doneson, Carrie Keranen, Greg Sextro, Marc Diraison, Mike Juarez
Director: Bill Plympton

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419. I Don't Expect Anyone to Believe Me, 2023

If you’re new to the story, I Don’t Expect Anyone to Believe Me feels difficult to understand. The film adaptation portrays the novel through abruptly cut sequences, meticulously framed naturalistic frames, and monologue and dialogue that mean more than what’s being said, on top of Juan Pablo’s gradual descent into a criminal network. It’s as disorienting as being in Barcelona feels for Mexican couple Juan Pablo and Val. However, this film feels like a new approach in adapting novels – the multiple perspectives and epistolary portions adeptly portrayed through typed up screens and alternating perspectives (and direction) between the couple. It doesn’t feel like something that you’ve likely seen before.

Genre: Comedy, Crime, Drama

Actor: Aimar Vega, Alexis Ayala, Ángel Zermen, Anna Castillo, Ariana Van X, Bel Gris, Bruna Cusí, Carmen Beato, Clara Roquet, Darío Rocas, Dario Yazbek Bernal, Jelen García, Juan Carlos Remolina, Juan Daniel Garcia Treviño, Juan Minujín, Natalia Portnoy, Natalia Solián

Director: Luis Fernando Frías de la Parra

Rating: R

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420. Goodbye Mother, 2019

	
In another country, you can forge a completely different life from the one you had in your hometown. For closeted LGBTQ+ individuals, moving to a more tolerant society allows you to explore facets of your sexuality that wasn’t possible previously. In Goodbye Mother, first generation immigrant Nau Van is confronted with the secrets he hid from his hometown, the secret that isn’t a secret in America. The conflict plays out in a familiar fashion, going through plenty of the usual experiences that coming out entails, but, while these are familiar, Goodbye Mother tugs at the reality Asian immigrants experience, and does so in a sweet and empathetic way.Genre: Drama, Romance
Actor: Hồng Ánh, Hồng Đào, Lãnh Thanh, Lê Thiện, Võ Điền Gia Huy
Director: Trinh Dinh Le Minh

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