306 Best Challenging Movies to Watch (Page 3)

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.

Based on Virginia Woolf’s novel, Orlando is a fitting adaptation for a groundbreaking story. Changing from man to woman, the titular time traveler is portrayed by the incomparable Tilda Swinton, breaking the fourth wall as if daring anyone to question her casting. But Swinton’s androgynous look and stellar acting make her the perfect choice for this. Her gaze is the anchor that we hold on to as the film glides through the novel’s multiple themes with ease. Through director Grace Potter’s indescribable vision, they create a fantastic film that blurs gender, sex, identity, and time together with the original novel itself.

Genre: Drama, Fantasy

Actor: Anna Farnworth, Anna Healy, Barbara Hicks, Billy Zane, Charlotte Valandrey, Cyril Lecomte, Dudley Sutton, George Antoni, Heathcote Williams, Jerome Willis, Jessica Swinton, Jimmy Somerville, John Grillo, John Wood, Kathryn Hunter, Lothaire Bluteau, Martin Wimbush, Mary MacLeod, Matthew Sim, Oleg Pogodin, Olivia Lancelot, Peter Eyre, Quentin Crisp, Robert Demeger, Roger Hammond, Sara Mair-Thomas, Sarah Crowden, Simon Russell Beale, Thom Hoffman, Tilda Swinton, Toby Jones, Toby Stephens, Viktor Stepanov

Director: Sally Potter

Rating: PG-13

Clocking in at just over four hours and shot in vivid color, Norte, the End of History stands not only as Filipino auteur Lav Diaz's best work since his earliest films, but as the easiest entry point into his unique filmography. Told on a sweeping yet intimate scale, the film has all the trademarks of Diaz's work: slow, lengthy shots; bursts of dense dialogue and philosophizing; and copious amounts of human despair and systemic corruption. As our three protagonists' souls (who rarely share the screen, if at all) are pushed to the limit after a terrible crime is committed, everything heads toward universal truths—the perseverance of love, and the inevitability of divine justice.

It can be difficult to recommend any film of this length and deliberate pace, but Norte remains a masterful example of how to use time itself to build a monumental story.

Genre: Crime, Drama

Actor: Angeli Bayani, Archie Alemania, Hazel Orencio, Mae Paner, Mailes Kanapi, Moira Lang, Noel Sto. Domingo, Perry Dizon, Sheenly Gener, Sid Lucero, Soliman Cruz

Director: Lav Diaz

In 2005, Palestinian olive farmer Emad Burnat bought a camera to document the birth of his new son, Jibreel. But what was intended as an act of celebration quickly grew into something else, as Burnat inadvertently became a documentarian of the oppression his West Bank village faced when a wall was erected through it and Palestinian farmland illegally appropriated by Israeli settlers. As we come to witness, this reluctant pivot is just another example of everyday life in Bil’in being forcibly reoriented by the occupation, as Burnat captures the daily struggles of life in the village and charts the innocence-shattering effect the occupation has on young Jibreel’s burgeoning consciousness. 

Over his footage of encroaching illegal settlements, the arrests of Palestinian children in the middle of the night, the point-blank shootings of blindfolded and handcuffed peaceful protestors — plus tender snapshots of nature and joyful events in the village — Burnat delivers a poetic, reflective narration that miraculously ties these horrible and hopeful images together. It's this intimacy of perspective that makes 5 Broken Cameras profoundly harrowing and unexpectedly transcendent — a personal document of oppression that is also a testament to the miraculous persistence of the human spirit, the resilience of life and the urge to seek beauty even under truly awful circumstances.

Genre: Crime, Documentary, Drama, War

Actor: Emad Burnat, Mohammed Burnat, Soraya Burnat

Director: Emad Burnat, Guy Davidi

Rating: NR

Nebraska is a poem distilled into a film. Peter Travers from Rolling Stone says "is it a comedy or a drama? Both at the same time, as life itself." Everything about it is perfect: the acting, the photography, the story. In case that's not enough and you need to know the plot to get convinced, I'll tell you that it's a road movie about a senile old man and his son. If you still want more information, you can Google it, but come on! You'll just be wasting time that would be better spent on watching this masterpiece.

Genre: Adventure, Drama

Actor: Angela McEwan, Anthony G. Schmidt, Bob Nelson, Bob Odenkirk, Bruce Dern, Devin Ratray, Franklin Dennis Jones, June Squibb, Mary Louise Wilson, Missy Doty, Rance Howard, Stacy Keach, Tim Driscoll, Will Forte

Director: Alexander Payne

Rating: R

All Quiet on the Western Front is a period epic that unflinchingly shows us the savagery and senselessness of war. Set at the tail end of World War I, it follows two main stories: that of German soldier Paul Bäumer (Felix Kammerer), whose boyish eagerness for warfare is diminished with each bloody step he takes towards the frontline, and that of Matthias Erzberger (Daniel Brühl), the real-life German politician tasked to negotiate a ceasefire between the French and German forces.

Grim and sobering, the movie will leave you nothing less than stunned after viewing. Like 1917 before it, All Quiet on the Western Front relies on the juxtaposition of raw brutality and peaceful quiet to effectively forward its anti-war message. The film is Germany’s official entry for the 2023 Academy Awards.

Genre: Action, Drama, History, War

Actor: Aaron Hilmer, Adrian Grünewald, Albrecht Schuch, André Marcon, Andreas Döhler, Anthony Paliotti, Anton von Lucke, Cyril Dobrý, Dan Brown, Daniel Brühl, Daniel-Frantisek Kamen, Devid Striesow, Edin Hasanović, Felix Kammerer, Felix von Bredow, Gregory Gudgeon, Hendrik Heutmann, Jakob Diehl, Joe Weintraub, Luc Feit, Marek Simbersky, Markus Tomczyk, Martin Němec, Michael Pitthan, Michael Stange, Michael Wittenborn, Moritz Klaus, Nico Ehrenteit, Peter Sikorski, Sascha Nathan, Sebastian Hülk, Sebastian Jacques, Thibault de Montalembert, Tobias Langhoff, Tomáš Weber

Director: Edward Berger

Rating: R

Even before any blood is inevitably shed during A Short Film About Killing (which serves as the expansion of another episode from director Krzysztof Kieślowski's Dekalog miniseries, alongside A Short Film About Love), there's something positively oppressive and sinister even just in the way the movie is shot. Kieślowski and cinematographer Witold Adamek use color filters to make the film deliberately ugly—as if the image is degrading right in front of us. Oftentimes shadows obscure the edges of the frame, shining a sickly yellow spotlight on the characters on screen. It's the perfect way to get right into the heads of these people existing in a lawless land driven by primal instinct.

When crime and punishment finally occur, they're equally difficult to watch unfold, but in different ways. Kieślowski lingers on the details—the tools and processes that we tell ourselves will make the act of killing easier. And what he's ultimately able to expose is how capital punishment has been made to seem humane, just, or necessary, when it's often even more barbaric, cruel, and unproductive than a crime borne of desperation. The very government that does nothing to address the roots of crime is the same one most eager to kill criminals instead.

Genre: Crime, Drama

Actor: Aleksander Bednarz, Andrzej Gawroński, Artur Barciś, Barbara Dziekan, Jan Tesarz, Jerzy Zass, Krystyna Janda, Krzysztof Globisz, Leonard Andrzejewski, Małgorzata Pieczyńska, Mirosław Baka, Olgierd Łukaszewicz, Władysław Byrdy, Zbigniew Borek, Zbigniew Zapasiewicz, Zdzisław Rychter, Zdzisław Tobiasz

Director: Krzysztof Kieślowski

An absolutely beautiful film about superficiality, arrogance, and heartbreak. It focuses on the life of Aydin, a retired actor who now lives very comfortably managing a small hotel and a number of other small properties. Throughout the film Aydin's image shifts as he tackles the problems of his rather typical life. Having said this, there is nothing else typical about this film. It captures human relationships with an almost frightening precision. It almost feels as though you have an inside view into someone's actual life as Aydin battles it out with his sister Necla and his young wife Nihal. To me this is easily one of the best dramas of the decade, and if you so much as like movies that focus on humans and their interactions, it will be that for you too.  Nuri Bilge Ceylan will make 3 hours pass more quickly than they ever have before.

Genre: Drama

Actor: Ayberk Pekcan, Demet Akbag, Ekrem İlhan, Emirhan Doruktutan, Haluk Bilginer, Mehmet Ali Nuroğlu, Mehmet Ali Nuroğlu, Melisa Sözen, Nadir Sarıbacak, Nadir Sarıbacak, Nejat İşler, Nejat İşler, Serhat Kılıç, Serhat Mustafa Kılıç, Serhat Mustafa Kılıç, Tamer Levent

Director: Nuri Bilge Ceylan

Rating: Not Rated, Unrated

Vortex, Gaspar Noé’s haunting exploration of death and dementia, begins with a dedication: “to all those whose brains will decompose before their hearts.” The statement sets the heartwrenching tone of the film, which follows an elderly couple—one with dementia and the other with a heart ailment—during their last days together. Noé cleverly depicts all this in a split-screen design, which evokes the fractured pattern of old-age thought. 

Noé’s mother struggled with dementia, and Noé’ himself suffered from a brain hemorrhage that nearly killed him, so Vortex is clearly a personal film. But even without knowing this, Vortex feels effortlessly dear and deeply intimate, like it could've only been done by a person with a first-hand experience of this tragedy. At once personal and universal, Vortex is a haunting and inventive ode to love, death, and everything in between.

Genre: Drama

Actor: Alex Lutz, Corinne Bruand, Dario Argento, Françoise Lebrun, Jean-Baptiste Thoret, Nathalie Roubaud, Stephane Derderian

Director: Gaspar Noé

Based on the Austrian novel, The Piano Teacher is as brilliant and as disturbed as its protagonist. The film follows Erika Kohut (Isabelle Huppert), the repressed masochist in question, and the trainwreck of a relationship that she develops with her student Walter Klemmer (Benoît Magimel). Their dynamic is undeniably toxic. Austrian auteur Michael Haneke frames each scene with clinical detachment, but it is absolutely brutal how the two characters try to assert control over each other, engage in sadomasochism, and repeatedly violate each other’s boundaries. Huppert’s heartrending performance fully commits to the merciless treatment Erika receives. But more tragic is the way Erika’s unusual relationship could’ve freed her, could’ve helped her process her abuse, and instead, reinforces her repression. It’s scary to make yourself vulnerable by admitting your desires, only for them to be used against you.

Genre: Drama, Romance

Actor: Anna Sigalevitch, Annie Girardot, Benoit Magimel, Cornelia Köndgen, Dieter Berner, Eva Green, Gabriele Schuchter, Georg Friedrich, Gerti Drassl, Isabelle Huppert, Karoline Zeisler, Klaus Händl, Liliana Nelska, Michael Schottenberg, Rudolf Melichar, Susanne Lothar, Udo Samel, Vivian Bartsch

Director: Michael Haneke

Rating: R

In Playground, we follow seven-year-old Nora as she navigates friends and school. Through her eyes (and often on her eye level), we witness her and her brother trying and often failing to fit in.

The film is an unfiltered account of their formative years, and possibly a reflection of our own. Commercials and kid-friendly media would have us believe that childhood is simple and pure, but the truth is it isn’t exempt from the major pitfalls of humanity. Children will mimic whatever they see, reasonable or otherwise, and the resulting order won’t always be ideal. Case in point: in the schoolyard, free of adult supervision, Nora and her peers push and tease and harass one another. 

It’s painful but relatable, a microcosm of our own complicated world, and though the film doesn’t shy away from the cruelties of bullying, it’s also filled with moments of empathy and warmth.

Genre: Drama

Actor: Anne-Pascale Clairembourg, Karim Leklou, Laura Verlinden, Sandrine Blancke, Simon Caudry

Director: Laura Wandel

The film stars Jake Gyllenhaal as Lou Bloom, an impromptu freelance videographer who begins covering the crime world in LA for a local TV station. Almost as dark as a mystery can get, it is disturbing, and plays out as a combination of "Drive" and "The Network". The film is visually stunning as well as immensely suspenseful. It then becomes almost impossible to look away, even when you're the most horrified by just how far Bloom is willing to go to reach success. Gyllenhaal's performance is widely compared to that of Robert De Niro in Taxi Driver, which should give you an idea of its caliber.

Genre: Crime, Drama, Mystery, Thriller

Actor: Alex Ortiz, Ann Cusack, Bill Blair, Bill Paxton, Bill Seward, Carolyn Gilroy, Chris Wolfe, Christina De Leon, Dale Shane, Dan Gilroy, Dig Wayne, Eric Lange, Holly Hannula, Jake Gyllenhaal, James Huang, Jamie McShane, Jonny Coyne, Kathleen York, Kent Shocknek, Kevin Dunigan, Kevin Rahm, Kiff VandenHeuvel, Leah Fredkin, Marco Rodriguez, Merritt Bailey, Michael Hyatt, Michael Papajohn, Myra Turley, Pat Harvey, Price Carson, Rene Russo, Rick Chambers, Rick Garcia, Riz Ahmed, Sharon Tay, Stephanie D'Abruzzo, Viviana Chavez

Director: Dan Gilroy

Rating: R

It's heartbreaking to realize that Happening, a film set in 1960s France tracking a young woman's journey to dangerously and desperately terminating her pregnancy, is still very much relevant and relatable to this day. Around the world, abortion is still inaccessible, if not completely illegal, and women still struggle to lay full claim to their bodies. A lot of girls grow up with pregnancy statistics meant to instill fear, but Happening brings all that to brilliant life in intimate and unrestrained detail. The fears and wants of our protagonist Anne (played precisely by Anamaria Vartolomei) are palpable throughout. Nothing is held back in this film, and if you find yourself sick in parts, then it has achieved its goal of realistically conveying what it's like to stay alive in a society that fails to recognize your needs. 

 

Genre: Drama, History

Actor: Alice de Lencquesaing, Anamaria Vartolomei, Anna Mouglalis, Cyril Metzger, Édouard Sulpice, Fabrizio Rongione, Francois Loriquet, Julien Frison, Kacey Mottet Klein, Leïla Muse, Louise Chevillotte, Louise Orry-Diquéro, Luàna Bajrami, Pio Marmaï, Sandrine Bonnaire

Director: Audrey Diwan

Rating: R