13 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.

, 2011

It might seem like a no-brainer that trying to make a comedy movie featuring a character with cancer is not a great idea. And while there may be a good share of failed attempts in that category, 50/50 is not one of them. And then it might come as a surprise that this subtle attempt at cancer comedy comes courtesy of Superbad creators Seth Rogen and Evan Goldberg. It also stars indie cutie Joseph Gordon-Levitt as the young and fit Adam Lerner, who works as a writer for public radio before learning that he has malignant tumors all along his spine. Between his overbearing mum (Anjelica Huston), slightly obnoxious but good-hearted bestie (Seth Rogen), self-help groups, and his therapist (played by Anna Kendrick), he struggles to find a way of acquiescing to his 50/50 chance of survival. Similarly, 50/50 strikes a delicate balance between the bromance gags, the date-movie elements, and the grave subject matter at its heart. It manages to mine humor, pathos, and simple honesty from a dark situation, and is not afraid to “go there”. The result is truly compassionate comedy.

Genre: Comedy, Drama

Actor: Adrian Glynn McMorran, Amitai Marmorstein, Andrea Brooks, Andrew Airlie, Anjelica Huston, Anna Kendrick, Beatrice King, Brent Sheppard, Bryce Dallas Howard, Cameron K. Smith, Chilton Crane, Christopher De-Schuster, D.C. Douglas, Daniel Bacon, Donna Yamamoto, Jason Vaisvila, Jessica Parker Kennedy, Jonathan Levine, Joseph Gordon-Levitt, Laura Bertram, Lauren Miller, Luisa D'Oliveira, Marie Avgeropoulos, Matt Frewer, Matty Finochio, P. Lynn Johnson, Peter Kelamis, Philip Baker Hall, Sarah Smyth, Serge Houde, Seth Rogen, Stephanie Belding, Stephen Colbert, Sugar Lyn Beard, Tom MacNeill, Veena Sood, Will Reiser, William 'Big Sleeps' Stewart, Yee Jee Tso

Director: Jonathan Levine

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, Annemarie Schleinzer, Annie Girardot, Benoit Magimel, Cornelia Köndgen, Dieter Berner, Eva Green, Gabriele Schuchter, Georg Friedrich, Gerti Drassl, Isabelle Huppert, Karoline Zeisler, Klaus Händl, Liliana Nelska, Luz Leskowitz, Martina Resetarits, Michael Schottenberg, Petra Reichel, Philipp Heiss, Rudolf Melichar, Susanne Lothar, Thomas Auner, Thomas Weinhappel, Udo Samel, Vivian Bartsch, William Mang

Director: Michael Haneke

Rating: R

Sometimes you can just tell a movie means way too much to the people who made it. That makes me want to watch it more than once, which is what I wanted to do with The Tale. But while I think it's such an amazing movie and everyone should watch it, I don't think I can stomach a second watch.. It is based on the director/writer Jennifer Fox's own story - recounting her first sexual experience at a very young age. It's about the stories we tell ourselves to deal with trauma, and in that sense, and with utmost honesty, it invites grief and closure for similar experiences. A powerful movie led by a powerful performance by Laura Dern as Jennifer.

Genre: Drama, Mystery, TV Movie

Actor: Chelsea Alden, Common, Daniel Berson, Deana Deatherage, Elizabeth Debicki, Ellen Burstyn, Emily Sandifer, Frances Conroy, Grant James, Gretchen Koerner, Isabella Amara, Isabelle Nélisse, Jaqueline Fleming, Jason Ritter, Jenson Cheng, Jered Meeks, Jessica Sarah Flaum, Jodi Long, John Heard, Juli Erickson, Katie Fairbanks, Laura Allen, Laura Dern, Lonnie Rashid Lynn Jr., Madara Jayasena, Madison David, Matthew Rauch, Mobin Khan, Noah Lomax, Paul Riley Fox, Pixie Hankins, Rebecca Chulew, Ricki Bhullar, Russell Bradley Fenton, Scott Takeda, Tarek Bishara, Thom Bishops, Tina Parker, Vincent Washington

Director: Jennifer Fox

Rating: Not Rated

, 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

While being known for co-writing the Dogme 95 manifesto, Lars von Trier’s first film after breaks his rules with built sets and music added in post. Still, Breaking the Waves has plenty of von Trier’s thematic preoccupations, challenging the notions between faithfulness and sexuality by positing a married couple who cannot indulge in marital pleasure, due to being paralyzed. While the premise leads to explicit scenes, it’s more harrowing than sexy, really. It’s terribly heartbreaking as Bess does all she can for her marriage, first by praying for her husband’s return, and then following his perverse wish, partly from guilt, but partly from pleasure, even when it goes contrary to her repressive church and community. Breaking the Waves may not be an easy watch, but regardless of what you personally feel about the morality of Bess’ actions, von Trier will nevertheless bring you to empathy.

Genre: Drama, Romance

Actor: Adrian Rawlins, David Bateson, Dorte Rømer, Emily Watson, Finlay Welsh, Gavin Mitchell, Jean-Marc Barr, John Wark, Jonathan Hackett, Katrin Cartlidge, Mikkel Gaup, Phil McCall, Robert Robertson, Roef Ragas, Sandra Voe, Stellan Skarsgård, Udo Kier

Director: Lars von Trier

Rating: R

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, Carlos Bermudez, Casey Affleck, Chris Gardner, Constance Jones, Dagger Salazar, 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., McColm Kona 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, Ari Aster, 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

There’s a cyclical tragedy at the heart of Bad Education, that starts with love, then continues in separation, and ends with hoping to redeem one’s self, and it would have felt repetitive if it wasn’t for the metafictional framing of Pedro Almodóvar. It boldly tackles the sexual abuse occurring in Catholic boarding schools, from which Almodóvar was educated under. It also explores it through a series of brilliant twists, as each reveal essentially repeats again and again, with each remix increasing the stakes, weaving a new layer to the love triangle, and exacerbating the consequences. Bad Education blends Enrique’s, and perhaps Almodóvar’s, life with fiction, with the brilliance and style Almodóvar is best known for.

Genre: Crime, Drama

Actor: Agustín Almodóvar, Alberto Ferreiro, Daniel Giménez Cacho, Fele Martínez, Francisco Boira, Francisco Maestre, Gael García Bernal, Javier Cámara, José María Yázpik, Juan Fernandez, Leonor Watling, Lluís Homar, Nacho Perez, Pau Poch, Petra Martínez, Pol Monen, Raul Garcia Forneiro, Sara Montiel

Director: Pedro Almodóvar

Rating: NC-17

Most people aspire to have families, deciding to form their own by marrying, bearing children, and if fertility makes that impossible, adopting one. The Official Story is centered on upper middle class Alicia, who’s already made the idyllic family life, with the last piece completed with her adoption of Gaby, but there are secrets held from her, or rather, there are realities that she chose not to listen to because of the painful implications. Writer-director Luis Puenzo juxtaposes the family secret to the violent ones the Argentine junta government kept from its citizens. It's not a subtle comparison– Puenzo makes it obvious– but it's an effective one, as Alicia has to reckon with the fact that she lies in bed with a stranger, as Argentina has to reckon with the remaining junta members and enablers.

Genre: Drama, History

Actor: Analia Castro, Andrea Tenuta, Aníbal Morixe, Augusto Larreta, Carlos Weber, Chela Ruíz, Chela Ruiz, Chunchuna Villafañe, Chunchuna Villafane, Fabián Rendo, Guillermo Battaglia, Héctor Alterio, Héctor Alterio, Horacio Erman, Hugo Arana, Jorge Chernov, Jorge Petraglia, Lidia Catalano, María Luisa Robledo, Marcos Woinsky, Maria Luisa Robledo, Norma Aleandro, Oscar Ferrigno Jr., Pablo Rago, Patricio Contreras, Paula Canals, Tony Middleton

Director: Luis Puenzo

Rating: Not Rated, NR

, 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

See, usually, when American violence in media is critiqued, it’s usually through analytic studies or overly exaggerated lectures stirring moral panic. Instead of doing this, however, auteur Michael Haneke decided to surpass the crime genre, playing with the form and emotions in Funny Games. It’s terrifying, not because it immediately delves into the violence, but because it starts off with an ordinary, innocuous visit, that gradually escalates into an unpredictable home invasion where two teenagers inflict needless violence in such a scary yet spectacular way, even involving the viewer into their shenanigans. Ironically, this led to Haneke creating a shot-for-shot American remake of this same story, but Funny Games’ break in form made Haneke a director to remember, as he started to film outside his native Austria after the standout thriller.

Genre: Drama, Horror, Thriller

Actor: Arno Frisch, Doris Kunstmann, Frank Giering, Stefan Clapczynski, Susanne Lothar, Ulrich Mühe

Director: Michael Haneke

Rating: R

After the 1975 release of the Maysles brothers’ Grey Gardens, Big and Little Edie Beale’s story captivated viewers and spawned a musical and a dramatized biopic about the reclusive, impoverished socialite mother-daughter duo. The Beales of Grey Gardens is a compilation of the remaining unreleased archival footage, released after the death of both subjects and David Maysles. For those unfamiliar with their story, the film might feel a bit random and contextless. But for Beale fans, and those familiar with their first documentary, this sticks close to the classic cinema vérité style of the Maysles, while also uncovering other sides of these interesting, eccentric former socialites, becoming a lovely tribute for them and their fans.

Genre: Documentary, Drama

Actor: Albert Maysles, David Maysles, Edith Bouvier Beale, Jerry Torre, Lois Wright

Director: Albert Maysles, David Maysles

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