10 Best Challenging Movies On Max (HBO Max)

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.

How do you make a film about the Holocaust feel new? How do you make the terrors feel fresh, like it was just in the news, without sounding redundant or without giving into the sensationalized and emotionally manipulative? For Director Jonathan Glazer, the answer lies in not what you show but what you don’t show. The Zone of Interest is shot from the point of view of Nazi Officer Rudolf Höss (Christian Friedel) and his wife Hedwig (Sandra Hüller), who live a dreamy life right next to the infamous Auschwitz death camp. Glazer frames them plainly and without flourish as they ignore (or, arguably, revel in) the glow of burning bodies, the howls of pain, and the billows of smoke coming from the torture chamber a wall away. It’s a powerful, nauseating contrast that turns the question from “How can they do this?” to “Who among us is committing the same things right now?” Who among us is casting a blind eye to the atrocities and genocide being committed at this very moment to our neighbors? The film, which is also a technical feat in terms of the way it’s shot (the crew and cameras remained hidden so that the actors were free to roam, as if in a play) is chilling and thought-provoking, and it will unnerve you for days on end.

Genre: Drama, History, War

Actor: Anastazja Drobniak, Christian Friedel, Daniel Holzberg, Freya Kreutzkam, Imogen Kogge, Jakub Sierenberg, Johann Karthaus, Klaudiusz Kaufmann, Lilli Falk, Luis Noah Witte, Marie Rosa Tietjen, Maximilian Beck, Medusa Knopf, Nele Ahrensmeier, Rainer Haustein, Ralph Herforth, Sandra Hüller, Sascha Maaz, Shenja Lacher, Thomas Neumann

Director: Jonathan Glazer

Rating: PG-13

Legend has it that director Derek Cianfrance had the co-stars and co-executive producers Michelle Williams and Ryan Gosling live together in the same house for a month in preparation of their roles. The fictional couple they play in Blue Valentine lived in the same house. True or not, this created the harsh proximity, intensity, and claustrophobia that is a hallmark of this production. Blue Valentine brings us painfully close to the couple's attraction as well as their agony.

In this way, Blue Valentine is a heart-breaking examination of the decaying shell of a once-bright marriage. As sad as it is sexy, it mixes intense flashbacks of past desire with the grim reality of married life's monotony. It boasts an electrifying performance from Michelle Williams and Ryan Gosling, who seamlessly combine tenderness and lust, rage and sadness. This is a guaranteed tear-jerker, so make sure you've brought your Kleenexes!

Genre: Drama, Romance

Actor: Alan Malkin, Ashley Gurnari, Barbara Troy, Ben Shenkman, Carey Westbrook, Enid Graham, Faith Wladyka, Ian Bonner, James Benatti, Jen Jones, John Doman, Joseph Basile, Mark Benginia, Marshall Johnson, Maryann Plunkett, Michelle Williams, Mike Vogel, Robert Russell, Ryan Gosling, Tamara Torres

Director: Derek Cianfrance

Rating: R

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

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, 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

, 2016

Here’s a based-on-a-true-story courtroom drama that transcends the limits of its genre by virtue of an incisive and unexpectedly prescient script. Twenty years before 2016 sent us hurtling through the looking glass and into a post-truth era, the idea that you could deny the facts as you pleased teetered terrifyingly on the brink of legitimacy when author David Irving (a suitably odious Timothy Spall) brought a UK libel suit against Deborah Lipstadt (Rachel Weisz), an academic whom he claimed had defamed him for calling him exactly what he was: a Holocaust denier.

The case was complicated by the fact that, at the time, the UK placed the burden of proof on the defendant — in other words, Lipstadt’s hotshot legal team needed to prove that the Holocaust happened and that Irving had wilfully misrepresented evidence demonstrating this. Denial captures that terrifying farcicality and the defense’s cleverly counterintuitive strategy: not allowing Lipstadt or Holocaust survivors to speak. If that sounds unsatisfying — this is the rare courtroom drama with no grandstanding speech from the protagonist — that’s the point, something the film’s title cleverly alludes to. Perhaps unexpectedly, Denial’s relevance has ballooned since its release, a fact that might hobble its hopeful ending but that only makes the rest all the more powerful.

Genre: Drama, History

Actor: Abigail Cruttenden, Alex Jennings, Amanda Lawrence, Andrea Deck, Andrew Scott, Caren Pistorius, Daniel Cerqueira, Edward Franklin, Elliot Levey, Harriet Walter, Helen Bradbury, Hilton McRae, Ian Bartholomew, Jack Lowden, Jackie Clune, Jeremy Paxman, John Sessions, Lachele Carl, Laura Evelyn, Mark Gatiss, Max Befort, Mick Jackson, Nicholas Tennant, Nikki Amuka-Bird, Paul Bailey, Paul Hunter, Pip Carter, Rachel Weisz, Sally Messham, Sara Powell, Sean Power, Timothy Spall, Todd Boyce, Tom Clarke Hill, Tom Wilkinson, Will Attenborough, Ziggy Heath

Director: Mick Jackson

Rating: PG-13

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: Augustine Frizzell, Barlow Jacobs, Brandi Price, Brea Grant, Carlos Bermudez, Casey Affleck, Chris Gardner, David Lowery, David Pink, Giovannie Cruz, Grover Coulson, Jonny Mars, Kenneisha Thompson, Kesha, Kesha Rose Sebert, Liz Cardenas, Liz Cardenas Franke, Liz Franke, McColm Cephas Jr., Nikita Patel, Rob Zabrecky, Rooney Mara, Sonia Acevedo, Will Oldham, Yasmina Gutierrez

Director: David Lowery

Rating: R

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, 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

, 2022

It’s a bold move, centering a drama around a creature as docile as a donkey, but EO pulls it off without ever leaning on the crutch of CGI. Instead, the film makes ingenious use of a hundred-year-old film technique: the Kuleshov effect. By splicing the image of the titular donkey’s placid, expressionless face against visual stimulus, the illusion of a genuine reaction is produced.

But don’t be mistaken: this is no twee Disney-esque tale of anthropomorphism. Inspired by the classic Au Hasard Balthasar, EO tracks the haphazard journey of a former circus donkey across Europe — one that is often depicted in surreal psychedelic reds instead of idyllic picture-book tones, and punctured by more horrors than joys (though we do, thankfully, get to see him munch away on some well-deserved carrot treats). EO’s docility frames him as a kind of holy innocent, making the cruelty meted out to him feel all the more like a grave violation of something sacrosanct. Seeing the world through his oft-neglected perspective also makes this a movie about humans by proxy — a fresh, empathetic approach that, even in its obvious dramatic liberties, makes us meditate on both the depth of experience that may be unfolding in our animal neighbors and our role in shaping it.

Genre: Drama

Actor: Isabelle Huppert, Kateřina Holánová, Lolita Chammah, Lorenzo Zurzolo, Mateusz Kościukiewicz, Sandra Drzymalska, Tomasz Organek, Waldemar Barwiński

Director: Jerzy Skolimowski

Rating: NR

Even if it doesn't provide the most comprehensive information about treatment and care for multiple sclerosis (MS)—especially for those who can't afford a ridiculously expensive stem cell transplant—this isn't really the point of Introducing, Selma Blair. This is still mostly a biographical documentary about a (self-confessed) "not-so-famous" celebrity, who gets to be incredibly honest about some of the privilege she enjoys, and how that privilege still doesn't make MS any easier. Blair's determination, her sense of humor, and her articulate way of expressing herself keep the film from descending into total sadness, but it also never shies away from the uglier, more difficult parts of her journey.

Genre: Documentary

Actor: Selma Blair

Director: Rachel Fleit

With its wildly different shifts between the film’s chapters, Bad Education feels like it doesn’t know what to do with itself, like plenty of newly graduated teenagers. The first chapter holds such visceral revulsion that it first feels like it would be a serious cautionary tale, commenting on how, without guidance, teenagers will led each other astray. However, its next chapter takes a more comedic route as the kids try to escape from gangsters and the police. While director Kai Ko reveals an excellent sense of direction and imagery, his style feels like it’s been wasted on ill-thought intentions and a poorly written script. Bad Education at least has stunning visuals and a short runtime to get through it all.

Genre: Crime, Drama, Mystery, Thriller

Actor: Berant Zhu, Cheng Chih-wei, Edison Song, Hong Yu Hong, Huang Hsin-Yao, Kai Ko, Kent Tsai, Kurt Hsiao, Leon Dai, McFly Wu, Ning Chang, Tzu-Chiang Wang

Director: Kai Ko