497 Best Challenging Movies to Watch (Page 20)

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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286. The Changeling, 2023

With its first episode, The Changeling might feel less scary and more romantic and historical than how a horror fantasy would seem like. The series shifts in and out of flashbacks, sometimes even having a flashback within a flashback, with dreamlike sequences that makes it take a while to figure out when and where the story is taking place. This causes the series to have some unusual pacing that might turn off viewers wanting a quick scare. But there’s a certain mystery to it, a certain anxiety captured as Apollo and Emmy disobey the Brazilian witch, as it recalls those negligent parents in familiar fantastic fairy tales. And as the series makes their flashbacks, there’s a certain fear that Apollo and Emmy might redo the same mistakes their immigrant parents have done before them. It makes for an intriguing take on the novel by Victor LaValle, one that captures a realistic fear that isn’t easy to depict.

Genre: Drama, Mystery, Sci-Fi & Fantasy

Actor: Adina Porter, Alexis Louder, Clark Backo, Jared Abrahamson, Lakeith Stanfield, Samuel T. Herring

Rating: TV-MA

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287. The Beast, 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: Alice Barnole, Bertrand Bonello, Dasha Nekrasova, Elina Löwensohn, George MacKay, Guslagie Malanda, Isabelle Prim, Julia Faure, Laurent Lacotte, Léa Seydoux, Lukas Ionesco, Marta Hoskins, Martin Scali, Rémi Canaple, Tiffany Hofstetter, Xavier Dolan
Director: Bertrand Bonello
Rating: NR

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288. Swan Song, 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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289. Soulmate, 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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290. Searching for Bobby Fischer, 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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291. Santa sangre, 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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292. Sankofa, 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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293. Reversal of Fortune, 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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294. Priscilla, 2023

	
There are a striking number of similarities between Priscilla and director Sofia Coppola’s earlier offering, Marie Antoinette: both revolve around 14-year-old girls hand-picked to be partners to more powerful men in long-unconsummated relationships, and both girls are emotionally cut adrift and forced to live in gilded cages. But where Coppola’s Barbie-pink historical biopic is punkily anachronistic and riotous, Priscilla is a far more muted affair. There are no wild parties at Graceland as there were at Versailles; instead, Priscilla’s emotional isolation, thousands of miles away from her family, is made disconcertingly clear in shots of the infatuated teenager (played by Cailee Spaeny) anxiously ruminating alone in endless lavish rooms while the decade-older King (Jacob Elordi) plays away. Elvis’ emotional manipulation of Priscilla is conveyed subtly but inescapably — and the full sickening, insidious effect comes to the fore thanks to Spaeny’s astonishing performance. Based on Priscilla Presley’s own memoir, this is a bubble-bursting biopic, and it’s so compelling and painfully immersive that we never feel, even for a moment, like we’re watching the B side — instead, Spaeny and Coppola convincingly assert that this was the real story all along.Genre: Drama, Romance
Actor: Alanis Peart, Ari Cohen, Cailee Spaeny, Conni Miu, Dagmara Domińczyk, Dan Abramovici, Dan Beirne, Deanna Jarvis, E. Fegan DeCordova, Emily Mitchell, Gwynne Phillips, Jacob Elordi, Jorja Cadence, Josette Halpert, Kamilla Kowal, Kelaiah Guiel, Kelly Penner, Luke Humphrey, Lynne Griffin, Mary Kelly, Olivia Barrett, R Austin Ball, Rodrigo Fernandez-Stoll, Sarah Dodd, Stephanie Moore, Stephanie Moran, Tim Dowler-Coltman, Tim Post
Director:  Sofia Coppola
Rating: R

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295. O-Bi, O-Ba: The End of Civilization, 1985

	
The thought of the end of the world and everything as we know it is scary, but going through it, and somehow surviving, can be a much more depressing idea. What do you do now? O-Bi, O-Ba: The End of Civilization is aptly titled, as its characters remain stuck inside a dome after a nuclear war, but the way the survivors’ hopes are warped, manipulated, and used against them can feel eerily familiar, and the way Piotr Szulkin unpacks this through Soft’s journey crafts a bleak, yet necessary examination of the fantasies we need in order to live in peace.Genre: Drama, Science Fiction
Actor: Adam Ferency, Elżbieta Zającówna, Henryk Bista, Jerzy Stuhr, Kalina Jędrusik, Krystyna Janda, Leon Niemczyk, Marek Walczewski, Mariusz Dmochowski
Director: Piotr Szulkin

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296. Marshland, 2014

	
When a regime falls, what follows isn’t a clean slate– it lingers, and it haunts those that were able to survive, part due to what was done to them and part to what they have done. Marshland ostensibly is a police procedural investigating a series of women murdered in rural Spain, but it’s also a clash of ideologies between New Spain, that wants to unearth the injustices that haven’t been acknowledged, and Old Spain, that wants to let sleeping dogs lie. The two plot threads don’t weave together as neatly as it could be, but La Isla Minima still works on both fronts, recreating that feeling of betrayal within that key transition period of Spain.Genre: Crime, Mystery, Thriller
Actor: Adelfa Calvo, Ana Tomeno, Ángela Vega, Antonio de la Torre, Javier Gutiérrez, Jesús Carroza, Jesús Castro, Manolo Solo, Mercedes León, Nerea Barros, Raúl Arévalo, Salva Reina
Director: Alberto Rodríguez

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297. Lost and Found, 1996

	
At one of the world’s largest shipping hubs, packages (and sometimes people) can get easily lost. It can be disheartening to lose something important, but that’s why it’s important to remember to check the lost and found. Through the titular niche industry, writer-director Lee Chi-Ngai crafts a existential love story that intertwines the lost souls of Hong Kong with a mournful melancholy marked with each repetition of Dance Me to the End of Love. It’s beautiful and depressing, and yet somehow Lee manages to tie all of the pieces together eloquently into something hopeful, despite the inevitable, if abrupt, ending.Genre: Drama, Romance
Actor: Alan Mak, Cheung Tat-Ming, Cheung Ying-Tsoi, Henry Fong, Henry Fong Ping, Hilary Tsui, James Yuen, Joe Ma, Jordan Chan, Josie Ho, Joyce Tang Lai-Ming, Kelly Chen, Maria Cordero, Michael Wong, Moses Chan, Steven Ma, Takeshi Kaneshiro, Teddy Chan
Director: Lee Chi-Ngai

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298. Insomnia, 1997

	
In a few seconds, a mistake can change your life forever. Insomnia is centered on a Swedish detective trying to solve a murder while trying desperately to cover a mistake made from the difficult mix of the fog and human exhaustion, but in doing so, his guilt, shame, and suspicion that no one would believe him due to past mistakes, weigh down on him, twisting the police procedural upon itself. Stellan Skarsgård holds an incredibly restrained performance throughout the entire film, and it’s well-framed by writer-director Erik Skjoldbjærg, whose use of cold white light in this debut feature eventually became the staple of on-screen Scandinavian noir.Genre: Crime, Mystery, Thriller
Actor: Bjørn Floberg, Bjørn Moan, Frode Rasmussen, Gisken Armand, Guri Johnson, Kristian Figenschow, Maria Bonnevie, Maria Mathiesen, Stellan Skarsgård, Sverre Anker Ousdal, Thor Michael Aamodt
Director: Erik Skjoldbjærg
Rating: NR

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299. House of Flying Daggers, 2004

	
If there’s one thing to say about House of Flying Daggers, it’s that it’s absolutely, absurdly, downright beautiful. The sets are lavishly designed, the landscapes are gorgeous, the colorful costumes are elaborately embroidered, the fight and dance choreography are breathtaking, every shot is colorful, and even the three leads in the love triangle are some of the most beautiful Chinese actors of the time (maybe, perhaps, of all time). That being said, some viewers might find that the beauty of each scene isn’t enough to carry through the film’s fairly convoluted plot, with everyone lying to each other all the time. There’s a thread here about being ordered into actions that would later be used to condemn you, and the way love intersects with that is fairly romantic stuff, but House of Flying Daggers doesn’t quite reach the emotional heights it could have had with a more streamlined script.Genre: Action, Adventure, Drama
Actor: Andy Lau, Andy Lau Tak-Wah, Chengyuan Li, Dandan Song, Hao Bojie, Hongfei Zhao, Jiusheng Wang, Jun Guo, Li Qiang, Liu Tengyuan, Shu Zhang, Song Dandan, Takeshi Kaneshiro, Wang Jiusheng, Yang Guang, Yongxin Wang, Zhang Shu, Zhang Ziyi, Zheng Xiao-Dong, Zhengyong Zhang, Ziyi Zhang
Director: Yimou Zhang, Zhang Yimou
Rating: PG-13

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300. Heavenly Creatures, 1994

Peter Jackson made the transition from splattery gross-out movies like Braindead to more respectable fare with Heavenly Creatures, the true story of an intense relationship between two teenage girls that culminates in the murder of one of their mothers.

As the girls’ friendship becomes unhealthier, they invent a secret world for themselves, amusingly including a heart-throb Orson Welles. This gives Jackson the opportunity to indulge in his love of fantasy, creating some dazzling hallucinatory sequences.

The fantasy element contrasts beautifully with the humdrum setting of ‘50s New Zealand, and the final tragedy is heart-breaking. The film also provided an auspicious debut for Kate Winslet, who is terrific as one of the misguided fantasists.

Genre: Drama, Fantasy

Actor: Barry Thomson, Ben Fransham, Clive Merrison, Darien Takle, Diana Kent, Elizabeth Moody, Geoffrey Heath, Gilbert Goldie, Glen Drake, Glenys Lloyd-Smith, Jed Brophy, Jesse Griffin, Kate Winslet, Liz Mullane, Lou Dobson, Melanie Lynskey, Moreen Eason, Peter Elliott, Peter Jackson, Ray Henwood, Sarah Peirse

Director: Peter Jackson

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