497 Best Challenging Movies to Watch (Page 11)

Staff & contributors

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.

Shattering the rules for how a biographical drama can look and be told, Paul Schrader's Mishima rejects the usual character study template in favor of a much more abstract attempt to understand a person through their art. Told in fragments that flit between Mishima's early life, dramatizations of his fiction novels, and the final day of his life, the film pieces together what it believes was the core of this person's life. Schrader's script (co-written with his brother Leonard Schrader) traces within Mishima's history a lifelong struggle with perceptions of his own masculinity and authority—as if he spent his every waking moment trying to compensate for a lack that he could hardly articulate. The character's eventual turn towards reactionary beliefs makes logical sense in the film, but remains baffling all the same.

With all of its talk about beauty—enhanced by Philip Glass' opulent musical score, and Eiko Ishioka's breathtaking production design that transforms Mishima's novels into tactile stage productions—the film conceals an incredibly dark heart. Mishima doesn't inspire sympathy so much as he inspires morbid fascination, and it's both a daring and frustrating choice to focus entirely on the character's harmful delusions without room for much else. Still, Schrader has constructed an unforgettable audiovisual experience that lingers long after it's over.

Genre: Drama, History

Actor: Alan Poul, Bandō Mitsugorō X, Chishū Ryū, Eimei Esumi, Fumio Mizushima, Go Riju, Haruko Kato, Hideo Fukuhara, Hiroshi Katsuno, Hiroshi Mikami, Hisako Manda, Jun Negami, Junkichi Orimoto, Ken Ogata, Kenji Sawada, Koichi Sato, Kunihiko Ida, Masahiko Sakata, Masato Aizawa, Masayuki Shionoya, Miki Takakura, Minoru Hodaka, Mitsuru Hirata, Naoko Ohtani, Naomi Oki, Naoya Makoto, Reisen Ri, Roy Scheider, Ryō Ikebe, Sachiko Hidari, Setsuko Karasuma, Shigeto Tachihara, Tadanori Yokoo, Toshio Hosokawa, Toshiyuki Nagashima, Tsutomu Harada, Yasuaki Kurata, Yasuhiro Arai, Yosuke Mizuno, Yuki Kitazume

Director: Paul Schrader

Rating: R

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Florence Pugh broke through with her powerhouse performance here as Katherine, a young woman who is “sold” into a coldly transactional marriage with a cruel and impotent merchant in 1800s Northern England. Lady Macbeth seems to begin as one thing — a gloomy period tale of oppression and feminist rebellion — but, on the strength of Pugh’s performance, pivots into an even bleaker subversion of that initial impression, the kind we haven’t really seen before.

When her disinterested husband takes a long leave of absence to tend to some business affairs, Katherine does more than just defy his command that she stay indoors: she begins an unabashed affair with one of her husband’s gruff groomsmen (Cosmo Jarvis), who ignites in her an obsessive passion that brings out her dark side. She’ll stop at nothing to remove any obstacles in the couple’s way — but, while her initial targets are arguably quite deserving of their fate, her scheme soon implicates the innocent. The creeping revelation that all the cruelty Katherine has been subjected to has brutalized her in turn comes as a shock, but this dramatic overturning of our expectations is made chillingly real by Pugh’s fierce, unfaltering performance.

Genre: Drama

Actor: Bill Fellows, Christopher Fairbank, Cliff Burnett, Cosmo Jarvis, David Kirkbride, Finn Burridge, Florence Pugh, Golda Rosheuvel, Ian Conningham, Kema Sikazwe, Naomi Ackie, Nicholas Lumley, Paul Hilton, Rebecca Manley

Director: William Oldroyd

Rating: R

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Not many places are worse to find a dead body than in the border of North and South Korea. The tensions are high, the trust is low, and the conflict between them hasn’t been resolved in more than half a century. Joint Security Area is centered on a whodunit surrounding two North Korean soldiers at the border, but Park Chan-wook crafts a compelling mystery not caused by international politics, but rather by friendship between soldiers in the lower ranks, a unity and brotherhood that’s tragically hidden and forced to separate because of lines made by their higher ups. It may not compare to Park’s more famous films, but Joint Security Area hinted at the filmmaker that was to come.

Genre: Drama, Mystery, Thriller, War

Actor: Byung Heon Lee, Byung-hun Lee, Christoph Hofrichter, Gi Ju-bong, Ha-kyun Shin, Herbert Ulrich, Jin Tae-hyeon, Ju-bong Gi, Kang-ho Song, Kim Kwang-il, Kim Myeong-su, Kim Myung-soo, Kim Tae-woo, Koh In-bae, Kwon Nam-hee, Lee Byung-hun, Lee Dae-yeon, Lee Do-yeop, Lee Han-wi, Lee Jong-yong, Lee Yeong-ae, Lee Young-ae, Myoeng-su Kim, Seo Jeong-gyu, Shin Ha-gyun, Shin Ha-kyun, Song Kang-ho, Tae-woo Kim, Yeong-ae Lee, Yoo Hyung-gwan, Yoon Hee-won

Director: Chan-wook Park, Park Chan-wook

Rating: Not Rated

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While many homophobic people like to think otherwise, there have been gay people all throughout history, some that have survived war and pandemics and persecution and even became widely renowned. Gods and Monsters is a more speculative than accurate biopic about Hollywood director James Whale, who was actually out during his career. That being said, it’s astounding how writer-director Bill Condon and lead Ian McKellen created such a bittersweet examination of the Lost Generation, not just of the loves that were lost but of the lives that could not be lived, the longing that could not be actualized. And the film takes a risky, but nuanced subversion in the way it examines the Hollywood system, subverting the roles Whale and Boone have placed on others and on themselves. It’s a daring portrayal of both homosexuality and of the film industry, one that’s emotionally poignant and ahead of its time.

Genre: Drama

Actor: Amir Aboulela, Arthur Dignam, Brendan Fraser, Celeste Lecesne, Cornelia Hayes O'Herlihy, Curtis Harrington, David Dukes, David Fabrizio, David Millbern, Ian McKellen, Jack Betts, Jack Plotnick, Jesse James, John Gatins, Judson Mills, Kent George, Kevin J. O'Connor, Lisa Darr, Lolita Davidovich, Lynn Redgrave, Mark Kiely, Martin Ferrero, Matt McKenzie, Michael O'Hagan, Owen Masterson, Pamela Salem, Rosalind Ayres, Sarah Ann Morris, Todd Babcock

Director: Bill Condon

Rating: R

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Murdering your spouse is bad, so it’s slightly bizarre how Drowning by Numbers has an unbothered, even amused, attitude towards its murders. Moments seem randomly placed, like the first scene of a girl jumping rope while listing the stars by name, and the film can be hard to follow, even if the production design and cinematography keep you drawn in. But as the film progresses, and Madgett’s son Smut enumerates the fictional games as if he was a historian of sorts, writer-director Peter Greenaway meticulously crafts a quirky, twisty crime comedy, where, like children’s games and the men in their lives, the murdering wives do what they do because they can get away with it. Drowning by Numbers cleverly plays with the way we treat folklore, structure, and rules, even down to the very medium Greenaway works with.

Genre: Comedy, Crime

Actor: Arthur Spreckley, Bernard Hill, Bryan Pringle, David Morrissey, Edward Tudor-Pole, Ian Talbot, Jane Gurnett, Janine Duvitski, Jason Edwards, Joan Plowright, Joanna Dickens, Joely Richardson, John Rogan, Juliet Stevenson, Kenny Ireland, Michael Fitzgerald, Michael Percival, Natalie Morse, Paul Mooney, Roderic Leigh, Trevor Cooper, Vanni Corbellini

Director: Peter Greenaway

Rating: R

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With a title like this, it was expected that Do Not Expect Too Much from the End of the World would be critical of today’s current circumstances, but the film takes a more startling approach. Radu Jude’s longest narrative feature is a day in the life of a disgruntled, underpaid production assistant, and as she drives between interviewees injured from work accidents, the film alternates between the black-and-white, terribly mundane reality, her Tiktok-filtered satirical rants as Bobiță, and an old colored film of a Romania decades past. It's a cynical depiction of how vulgar it is to be alive today, but it’s also more honest as Jude refuses to cling to the past.

Genre: Comedy, Drama

Actor: Adina Cristescu, Adrian Nicolae, Andi Vasluianu, Dorina Lazăr, Ilinca Manolache, Ioana Iacob, Katia Pascariu, László Miske, Nicodim Ungureanu, Nina Hoss, Ovidiu Pîrșan, Rodica Negrea, Șerban Pavlu, Uwe Boll

Director: Radu Jude

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Earnest, beautiful, and tender, Luca Guadagnino's Bones and All is many things: a road trip movie that sweeps the midwest deserts of 1980s America; a coming-of-age story that brings together two outsiders into an understanding world of their own; and a cannibal film that is unflinchingly flesh deep in its depiction of the practice. Bizarrely, these seemingly disparate elements work harmoniously to create a film that you won't soon forget, not least because of its rawness. 

As the aforementioned outsiders, Maren and Lee (Taylor Russell and Timothée Chalamet, respectively) are bewitching—individually sure but especially when they're together. They have a bond that is quite difficult to replicate onscreen, charged as it is with so much chemistry and warmth. The background players also bring their a-game when called for, especially Mark Rylance as the disturbing stalker Sully, Michael Stuhlbarg as the creepy but good-willed Jake, and Chloë Sevigny as Maren's stark mad mother. 

It's worth repeating that this movie goes all in on the gore, so steer clear if you don't have the heart for these sorts of things. But if you do, the viewing experience is rewarding. Bones and All is as romantic as they get, and rather than bury its message, the many layers on top of its core serve as a meaningful puzzle to unpack and unravel long after the credits roll.

Genre: Drama, Horror, Romance

Actor: Andre Holland, Anna Cobb, Brady Gentry, Chloe Sevigny, Christine Dye, David Gordon Green, Hannah Barlow, Jake Horowitz, Jenny McManus, Jessica Harper, Johanna McGinley, Madeleine Hall, Marcia Dangerfield, Mark Rylance, Michael Stuhlbarg, Sean Bridgers, Taylor Russell, Timothée Chalamet, Tom O'Brien

Director: Luca Guadagnino

Rating: R

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Twisted yet deep. Sad yet interesting. Slow yet exhilarating. A Ghost Story is an incredible artistic achievement. With hardly any dialog, and breathtakingly long takes in its first half, it manages to bring you in its own creepy world and not let go until you feel completely lonely. Starring Rooney Mara and Casey Affleck as a loving couple who are hit with a horrible tragedy, the beginning is slow, and it's not a plot driven movie, but if you give it a chance it will blow your mind.

Genre: Drama, Fantasy, Romance

Actor: Afomia Hailemeskel, Augustine Frizzell, Barlow Jacobs, Brandi Price, Brea Grant, Bryan Pitts, Carlos Bermudez, Casey Affleck, Chris Gardner, Constance Jones, Dagger Salazar, David Lowery, David Pink, Giovannie Cruz, Grover Coulson, Jonny Mars, Juan Fiol, Kenneisha Thompson, Kesha, Kesha Rose Sebert, Liz Cardenas, Liz Cardenas Franke, Liz Franke, McColm Cephas Jr., McColm Kona Cephas Jr., Nikita Patel, Rachel Chambers, Richard Krause, Rob Zabrecky, Rooney Mara, Savanna Sears, Sonia Acevedo, Will Oldham, Yasmina Gutierrez

Director: David Lowery

Rating: R

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Good parents, of course, try to push their children to better outcomes, but abusive parents, under the guise of this idea, turn this into restrictive control, where failure is irredeemable, expectations become orders, and the said child is blamed for everything that goes wrong. Udaan depicts this fraught father-son relationship realistically. It’s a tough watch because of how realistic the abuse was portrayed, but the film soars with the way it doesn’t paint Rohan only as a victim, but rather as a boy able to find his way through empathy and kindness despite the terrible way his father treats him. There’s a sense of genuine hope Udaan has that many other films forget, and it’s an important perspective we should try to remember.

Genre: Drama

Actor: Aayan Boradia, Akshay Sachdev, Anand Tiwari, Jayanta Das, Manjot Singh, Raja Hudda, Rajat Barmecha, Ram Kapoor, Ronit Roy, Sanjay Gandhi, Shashi Sharma, Shaunak Sengupta, Varun Khettry, Vikas Kumar, Vikramaditya Motwane

Director: Vikramaditya Motwane

Rating: Not Rated, R

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It’s bold to make a film about a legendary icon of cinema, but it’s even bolder to make one about Orson Welles. Best known for making Citizen Kane (universally agreed upon as one of the best movies ever made), Orson Welles is the renegade filmmaker whose works and techniques form the foundation of modern narrative filmmaking today. In his eyes, he asserts that the best films are made by accident. However, armed with archival footage and interviews with those closest to Welles, director Morgan Neville dares to question one of cinema’s biggest geniuses by examining the production of his last unfinished film, the Hollywood satire The Other Side of the Wind. While Welles was undeniably genius - able to inscrutably visualize a film without scripts - it’s easy to see how his tendency to stoke conflict for art could be so self-destructive. This film presents Welles as he is - both a cinema maverick and also an overly demanding artistic tyrant.

Genre: Documentary, Drama

Actor: Alan Cumming, Andrés Vicente Gómez, Cameron Mitchell, Cybill Shepherd, Danny Huston, Dennis Hopper, Dominique Antoine, Frank Marshall, Gary Graver, George Stevens Jr., Henry Jaglom, Jeanne Moreau, John Huston, Joseph Cotten, Joseph McBride, Keith Baxter, Larry Jackson, Michael Fitzgerald, Neil Canton, Norman Foster, Oja Kodar, Orson Welles, Peter Bogdanovich, Peter Jason, Rich Little, Robert Random, Simon Callow, Steve Ecclesine, Yves Deschamps

Director: Morgan Neville

Rating: TV-MA

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While many Palestinians had to leave their homeland, there are some families that stayed within the region. One such family is that of Palestinian director Elia Suleiman. The Time That Remains is a semi-biographical film that depicts each generation of the family in excellently framed, colorful shots, but while each scene is a beauty to watch, there’s an ugly undercurrent with the way one group is treated over the other. The film contrasts the stoic actions of Elia’s father Fuad and that of the Israeli soldiers, teachers, and nurses around them, and the contrast channels a dry sort of humor that pokes at the absurdity the occupation places 20% of its citizens through. It’s a smart, subtle way to depict the rage felt by the many people that remained in the area, as well as the sadness they must have felt with the loss, the pain, and the displacement they’ve gone through.

Genre: Drama, History

Actor: Ali Suliman, Amer Hlehel, Elia Suleiman, Maisa Abd Elhadi, Menashe Noy, Mira Awad, Saleh Bakri, Samar Qudha Tanus, Shafika Bajjali, Zuhair Abu Hanna

Director: Elia Suleiman

Rating: PG-13

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Palm Springs, the latter of which also stars Cristin Milioti in a twisty vacation adventure. Milioti of course steals the show as a woman who would rather drown herself in a police-level investigation than deal with her own existential problems, but the show’s strong cast, which includes The Good Place’s William Jackson Harper and Parks and Recreation’s Nick Offerman solidifies The Resort as one of the most intriguing and exciting shows today. 

Genre: Comedy, Fantasy, Mystery

Actor: Cristin Milioti, Gabriela Cartol, Luis Gerardo Méndez, Nick Offerman, Skyler Gisondo, William Jackson Harper

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In this documentary about John Allen Chau — the American Christian missionary reportedly killed when he tried to preach the Gospel to one of the last uncontacted groups in the world — a participant muses about the “fine line between faith and madness.” The hazy border where one ends and the other begins is the focus of this doc, and it makes for a fascinating challenge of audience’s open-mindedness.

The film presents Chau’s perspective through scattered interviews with friends and readings of the diary he left behind, but it also features interviews with surviving, persistent adherents of the same radical evangelicalism that inspired Chau to preach the Gospel to the North Sentinelese people (something he believed was a prerequisite for the Second Coming of Jesus). The filmmakers treat these highly controversial perspectives with a light touch, never explicitly challenging Chau’s peers, but strong balance is provided via the voices of vehement opponents of this ideology. Providing equal weighting to both sides is an unusually hands-off approach, one that might easily be misread as tacit approval from the filmmakers. Ultimately, though, anyone watching this with an open mind will still come to the same moral conclusion — you’ll just be better informed about it.

Genre: Documentary

Actor: Dan Davis, Daniel Everett, David Shih, Lawrence Kao, Levi Davis, Pam Arlund

Director: Amanda McBaine, Jesse Moss

Rating: PG-13

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