330 Best Challenging Movies to Watch (Page 10)

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.

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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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: Bernard Hill, Bryan Pringle, David Morrissey, Jane Gurnett, Janine Duvitski, Jason Edwards, Joan Plowright, Joanna Dickens, Joely Richardson, John Rogan, Juliet Stevenson, Kenny Ireland, Michael Percival, Paul Mooney, Trevor Cooper

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: 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

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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, Frank Marshall, Gary Graver, George Stevens Jr., Henry Jaglom, Jeanne Moreau, John Huston, Joseph Cotten, Joseph McBride, Keith Baxter, Michael Fitzgerald, Neil Canton, Norman Foster, Oja Kodar, Orson Welles, Peter Bogdanovich, Peter Jason, Rich Little, Robert Random, Simon Callow

Director: Morgan Neville

Rating: TV-MA

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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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In 1994, Danish auteur Lars von Trier came up with a TV series called The Kingdom, an absurd supernatural comedy that takes place in a rundown hospital in Copenhagen. The show was well-received enough to warrant a second season, but just as von Trier was polishing up the third and final installment, the deaths of more than one lead actor pressed pause on the project, till now.

More than 10 years in the making, The Kingdom part III, also called Exodus, is still very much centered on the weird patients and staff members that populate the Riget hospital, as well as the possible evil buried beneath it. The comedy/horror has a robot dishwasher and a giant head. Danes and Swedes are perennially at war with each other. Willem Dafoe and Alexander Skarsgard make odd cameos.

I’m not sure it’s possible to write a coherent synopsis without sounding like I’ve fallen off the rails, but know that it is a unique headscratcher of a show, more interesting as an experience than anything else. Von Trier was also openly inspired by Twin Peaks, in making it, so David Lynch fans in particular will truly enjoy diving into this world.

Genre: Comedy, Drama, Fantasy, Horror, Mystery, Thriller, TV Movie

Actor: Annevig Schelde Ebbe, Baard Owe, Benny Hansen, Benny Poulsen, Birgitte Raaberg, Birte Tove, Claus Nissen, Claus Strandberg, Danica Curcic, Dick Kaysø, Else Petersen, Erik Wedersøe, Ernst-Hugo Järegård, Finn Nielsen, Ghita Nørby, Gordon Kennedy, Helle Virkner, Henning Jensen, Henrik Koefoed, Holger Juul Hansen, Holger Perfort, Jens Okking, Julie Wieth, Kirsten Rolffes, Kurt Ravn, Lars Lunøe, Lars von Trier, Laura Christensen, Lene Vasegaard, Lise Schrøder, Mette Marckmann, Mette Munk Plum, Michael Moritzen, Morten Eisner, Nis Bank-Mikkelsen, Ole Boisen, Ole Dupont, Otto Brandenburg, Paul Hüttel, Peter Gilsfort, Peter Mygind, Solbjørg Højfeldt, Solveig Sundborg, Søren Elung Jensen, Søren Hauch-Fausbøll, Søren Pilmark, Søren Steen, Thomas Bo Larsen, Tove Maës, Udo Kier, Ulrik Cold, Vic Carmen Sonne, Vita Jensen, Willem Dafoe

Director: Lars von Trier, Morten Arnfred

Rating: TV-MA

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This fiery coming-of-age drama has an unlikely origin story: director Jonas Carpignano was first introduced to the sprawling Roma clan that makes up most of the movie’s cast when one of them stole his car while he shot another film. The charismatic Amato family made such an impression on him that he decided to center a movie around their real lives, naming it for the insular neighborhood they live in on the outskirts of a Southern Italian town.

The Amatos are part of a much-maligned ethnic minority, but not the only one in the film. The Ciambra pokes at the idea of solidarity between the Amatos and local African migrants: while his elders are quick to reject the idea, plucky 14-year-old Pio (Pio Amato) flits across these invisible borders and bonds with Ayiva (Koudous Seihon). But Pio is desperate to win the respect of the men in his family, who might then allow him to take part in their criminal exploits — a crisis point The Ciambra chronicles with raw emotion. This is a movie whose grit and bleakness often recall the uncompromising gaze of neo-realist classics, as a child is heartbreakingly forced to declare his allegiances in the dog-eat-dog world his elders can’t imagine an alternative to.

Genre: Crime, Drama

Actor: Damiano Amato, Francesco Papasergio, Iolanda Amato, Koudous Seihon, Patrizia Amato, Pio Amato, Rocco Amato, Susanna Amato

Director: Jonas Carpignano

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Stutz is Jonah Hill’s loving tribute to his therapist Phil Stutz, a smart and empathetic man who’s dedicated his entire life to helping people. The conversations between them, deeply personal and vulnerable, are meaningful in themselves, but Stutz also works as a helpful instruction on how to be your best self and as a metanarrative on telling honest stories on a medium as seemingly artificial as film (it is similar to Bo Burnham’s Inside in that way).

Stutz is at once experimental and comforting, a real gem especially for people with an interest in psychoanalysis and alternative psychiatry. It’s at its best when the two men deal with uncomfortable truths in the kindest of ways, and it's sure to be something people will return to often for advice and solace. Fun fact: the documentary was co-produced by Joaquin Phoenix and Rooney Mara.

Genre: Documentary, Drama

Actor: Jonah Hill

Director: Jonah Hill

Rating: R

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