105 Best Challenging Movies On Itunes (Page 4)

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.

It is hard to be unmoved by how Die Beautiful defies conventions and explores the essence of identity, acceptance, and resilience. Centered around the life of Trisha, a transgender woman with a passion for beauty pageants, the film takes us on a rollercoaster of emotions as we witness Trisha's life unfold, both in joyous moments and in the face of painful degradation and assault. The film seamlessly weaves together humor, tenderness, and raw vulnerability, delivered stunningly by its lead, Paolo Ballesteros. With other films such as Kalel, 15 and Bwakaw under his belt, director Jun Lana continues to meld reality with hope, injecting kindness and heart into much-needed queer stories.  

Genre: Comedy, Drama

Actor: Adrian Alandy, Albie Casiño, Cedrick Juan, Christian Bables, Eugene Domingo, Gladys Reyes, I.C. Mendoza, Iza Calzado, Jade Lopez, Joel Torre, Kokoy de Santos, Lou Veloso, Luis Alandy, Paolo Ballesteros

Director: Jun Lana, Jun Robles Lana

Rating: TV-14

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

Taking 23 years until its completion, The Tragedy of Man is quite possibly the most ambitious film ever made, not just in its animation, but also in its scope. It’s quite fitting, as an adaptation of the classic Hungarian play, as Imre Madách’s story sets out to question not just the individual’s purpose, but the purpose of humanity as a whole, with writer-director Marcell Jankovics giving life to the play through the historical art styles of past civilizations that shifted today’s Western world, as well as adding what has happened after the play’s publication in 1861. While the film’s length can be daunting, being the Western animated feature in the world, the dialectic hits at the heart of this absurd existence, informed by the cynicism formed after Hungary’s fall of communism in 1989. The Tragedy of Man isn’t an easy film to watch, considering the themes, but it’s an interesting vision of humanity, illustrated in such an interesting way.

Genre: Animation, Drama, History

Actor: Ágnes Bertalan, Mátyás Usztics, Piroska Molnár, Tamás Széles, Tibor Szilágyi

Director: Marcell Jankovics

Feminism has made plenty of strides in multiple areas, but even in the era of free love, talking about sex was difficult, and certain figures were dismissed just because of it. The Disappearance of Shere Hite reexamines the titular forgotten feminist figure that simply focused on the female orgasm, giving a second look at her immediate rise and fall in the American media, and the reasons for her leaving the country. With Dakota Johnson’s soft voice, an excellent selection of archival footage, and Hite’s deeply personal words, the film paints a portrait of a mild-mannered, self-possessed woman, but it also reveals the heartbreakingly repetitive vitriol that affects these open discussions today.

Genre: Documentary

Actor: Dakota Johnson, Shere Hite

Director: Nicole Newnham

In The Beasts, the idyllic semi-retirement that a French couple seeks in the Galician countryside — growing organic vegetables, fixing up abandoned farmhouses — devolves into a terrifying slow-burn nightmare. This beautifully shot yet spiritually ugly thriller plunges us straight into an atmosphere of crackling social tension that never abates. We begin after the event that turns local farmer Xan (Luis Zahera) and his brother Loren (Diego Anido) against French transplants Antoine (Denis Ménochet) and Olga (Marina Foïs): the latter two have vetoed the sale of land to a wind turbine company in favor of preserving the village’s rustic character. Incensed by what he sees as the theft of his birthright by an outsider, Xan orchestrates a steadily intensifying campaign of terror against the couple.

Though much slighter than the physically imposing Ménochet, Zahera makes for a profoundly menacing presence, and Xan’s seemingly endless appetite for hostility and vindictiveness charges the film with a deeply unsettling sense of inevitability. His performance alone would mark The Beasts as a standout, but an unexpected switch in character focus late on in the film wrests it out of Xan’s grasp and reorients the movie as a study of grim resolve — making it a film of two equally remarkable halves.

Genre: Drama, Thriller

Actor: David Menéndez, Denis Ménochet, Federico Pérez Rey, Luis Zahera, Luisa Merelas, Machi Salgado, Marie Colomb, Marina Fois, Xavier Estévez

Director: Rodrigo Sorogoyen

, 2022

Filled with dense conversations about classical music and cryptic suggestions of a guilty conscience, Tár makes for a challenging watch that rewards patient viewing. The film is ultimately a study of power in an industry built on preserving centuries-old traditions—which makes the character of Lydia Tár, as a queer woman and as a proud, egotistical conductor, such an anomaly in this world. Certain strange choices by the end notwithstanding, this is a movie that leaves itself wide open to interpretation to its view on karma, accountability, and cycles of power. And Cate Blanchett is as good as the awards say: fully immersed in Lydia's ways of arrogant self-preservation, and twitching at every ambient noise that reminds her how fake she truly is.

Genre: Drama, Music

Actor: Adam Gopnik, Alec Baldwin, Alexandra Montag, Allan Corduner, Alma Löhr, André Röhner, Artjom Gilz, Cate Blanchett, Christoph Tomanek, Diana Birenytė, Ed White, Frank Röth, Jessica Hansen, Johann von Bülow, Johanne Murdock, Julian Glover, Kenneth Won, Lee Sellars, Lucie Pohl, Lydia Schamschula, Marie-Anne Fliegel, Marie-Lou Sellem, Mark Strong, Mila Bogojevic, Murali Perumal, Nina Hoss, Noémie Merlant, Sam Douglas, Sarah Bauerett, Sophie Kauer, Sydney Lemmon, Tilla Kratochwil, Vincent Riotta, Vivian Full, Xenia Assenza, Zethphan Smith-Gneist

Director: Todd Field

Our Children opens at the harrowing end of the true story it’s based on: with the image of a distraught mother (Émilie Dequenne) in a hospital bed, begging a police officer to ensure that her children — who have just predeceased her — are buried in Morocco. From this ominous beginning, the film rewinds into a jarringly sunny flashback of lovebirds Murielle (Dequenne) and Mounir (Tahar Rahim) to tell this horrifying story from the start.

What follows is much less obviously dramatic: Our Children shifts into slow-burn psychological thriller territory as we watch the gradual breaking down of Murielle at the hands of Mounir’s adoptive father André (Niels Arestrup), a wealthy white doctor who has used his status to insinuate himself into the lives of Mounir and his family back home in Morocco. This is a very subtle study of manipulation, one that hinges entirely on the performances of the trio, who fill with nuance roles that could easily have been tabloid caricatures. Above all, though, this is Dequenne’s film, and it’s the devastating ways she shows the life gradually being sucked out of Murielle that makes Our Children so difficult to shake off.

Genre: Drama, Romance

Actor: Baya Belal, Claire Bodson, Émilie Dequenne, Mounia Raoui, Niels Arestrup, Redouane Behache, Stéphane Bissot, Tahar Rahim

Director: Joachim Lafosse

Rating: NR

As a crime thriller, Holy Spider is taut and terrifying, a modern noir that manages to unnerve despite the familiar moves it employs. The cat and mouse chase between serial killer and investigative reporter, for instance, is a classic tale, but that doesn’t make Holy Spider any less gripping. The film benefits from artful camerawork, considered acting (as the daring journalist Rahimi, Zar Amir Ebrahimi nabbed the Best Actress award at Cannes), and most of all a nuanced take on the situation in Iran. 

Despite having a clear stance against violence and corruption, nothing in Holy Spider is black and white. Contradictions abound, and even when presented with brief moments of justice, we’re left scratching our heads looking for more. Such is the case when the system, and not just an individual, is the true pest. 

Genre: Crime, Drama, Horror, Thriller

Actor: Ariane Naziri, Majd Eid, Mehdi Bajestani, Nima Akbarpour, Sara Fazilat, Sina Parvaneh, Zar Amir Ebrahimi

Director: Ali Abbasi

Dogtooth is a bonkers tale about three teenagers who live an isolated life on their family’s estate due to strict rules set by totalitarian parents. Their vocabulary is limited and their perception of the world is strange. They’re taught that cats are bloodthirsty monsters, that disobedience is grounds for horrific punishment, and that the world outside the house will kill them.

Equal parts bizarrely funny and disturbingly terrifying, director Yorgos Lanthimos pulls no punches with this fascinating examination of authoritarianism. As usual with his actors, they are directed to deliver lines in a matter-of-fact, often even deadpan manner, making the escalating lies and deceptions more and more unsettling as the film goes on. Thimios Bakatakis’ cinematography also places the twisted tale in a home that has a somewhat dreamlike beauty.

Those who enjoy dark, comical situations told with dry humor will be amused by Dogtooth. Those who enjoy stories that quietly build up to gruesome conclusions will also be amused by Dogtooth. It takes a unique mind to depict nameless children being subjugated and stripped of the fundamentals of conceptualization in an isolated world, and treat it as an absurdist comedy rather than a flat-out horror film. Lanthimos does it.

Genre: Drama

Actor: Alexander Voulgaris, Angeliki Papoulia, Anna Kalaitzidou, Christos Stergioglou, Hristos Passalis, Mary Tsoni, Michele Valley, Sissi Petropoulou, Steve Krikris

Director: Yorgos Lanthimos

Between its maximalist production design and increasingly dark comedic set pieces, the most striking thing about Damien Chazelle's critically misunderstood industry satire is how it strikes a tone closer to tabloid gossip than anything else. As opposed to the clockwork precision of Chazelle's Whiplash, or the dreaminess of La La Land, Babylon's restlessness doesn't resemble Hollywood spectacle so much as it begins to feel like an unscratchable itch, desperate to feel anything. The film ends up trying to say so much that it threatens to say nothing at all, but its vision of cinema becoming reality is so potent that just the experience is more than worth getting lost in.

Genre: Comedy, Drama

Actor: Aaron Oltman, Albert Hammond Jr., Alex Reznik, Alexandre Chen, Andrew Hawtrey, Anna Chazelle, Anna Dahl, Anthony Burkhalter, Ariel Flores, Armando Cosio, Benjamin Jacobson, Bob Clendenin, Brad Pitt, Bregje Heinen, Bryan Scott Johnson, Chloe Fineman, Chris Doubek, Christopher Allen, Cici Lau, Circus-Szalewski, Cyrus Hobbi, Danny Jolles, David Abed, David Ury, Dean Anderson, Diego Calva, Dorian Martin, E.E. Bell, Eamon Hunt, Eric Roberts, Ethan Suplee, Evan Greer, Flea, Frederick Koehler, Freya Parker, Hansford Prince, J.C. Currais, James Crittenden, James Vincent, James Wellington, Jean Smart, Jeff Garlin, Jennifer Grant, Jeremy Roberts, Jim O'Brien, Jimmy Ortega, Joe Dallesandro, Joey de Leon, John Kerry, John Macey, John Mariano, John Polite, Johnny Britt, Jonathan Ohye, Jonathan Thomson, Jordan Seigel, Jovan Adepo, Kaia Gerber, Karen Bethzabe, Karina Fontes, Karolina Szymczak, Katherine Waterston, Katia Gomez, Kenajuan Bentley, Kevin Symons, Kevin Toney, Lewis Tan, Li Jun Li, Lukas Haas, Marc Platt, Marcos A. Ferraez, Margot Robbie, Mateo Pollock, Mather Zickel, Max Minghella, Mike C. Manning, Miraj Grbić, Nana Ghana, Olivia Hamilton, Olivia Wilde, P. J. Byrne, Pat Skipper, Patrick Fugit, Pete Ploszek, Phoebe Tonkin, Ric Sarabia, Richard Clarke Larsen, Robert Beitzel, Robert Morgan, Rory Scovel, Ryan Porter, Samara Weaving, Sarah Ramos, Sean O'Bryan, Shane Powers, Sol Landerman, Spike Jonze, Taylor Hill, Taylor Nichols, Telvin Griffin, Terry Walters, Tobey Maguire, Todd Giebenhain, Trisha Simmons, Troy Metcalf, Tyler Seiple, Vanessa Bednar, Walker Hare, William Roper

Director: Damien Chazelle

Rating: R

Alejandro González Iñárritu's cleverly layered directorial feature film debut follows three persons whose lives are connected by a car crash in Mexico City. It directly involves two of them: a young man who enters the world of dogfighting to earn enough to elope with his sister-in-law, and a supermodel whose life is changed for the worse after she is fatally injured. The third segment of the film centers on a mysterious homeless man on the street who witnesses the crash.

The title, Amores Perros, refers to the characters’ love of dogs as well as love being a source of misery, and it’s a hint of the chaotic, unforeseen circumstances they each face. Iñárritu’s film shows his brilliance in direction. Despite the film being an early work, his ingenuity shines through and the compelling performances propel all three stories to gritty heights.

Cut-throat editing, handheld cinematography, and Guillermo Arriaga’s intricate screenplay flesh out each character. The viewers are pushed to the edge of their seats as we navigate the gripping miseries of life along with the rest of the cast. The tightly woven film is a painful must-watch, a brutal and uncompromising look at despair and animalistic aggression among humans that is also mirrored in the cruelty their dogs suffer.

Genre: Drama, Thriller

Actor: Adriana Barraza, Alvaro Guerrero, Dagoberto Gama, Dunia Saldívar, Emilio Echevarría, Gael García Bernal, Gerardo Campbell, Goya Toledo, Gustavo Muñoz, Gustavo Sánchez Parra, Humberto Busto, Jorge Salinas, José Sefami, Laura Almela, Marco Perez, Mauricio Martínez, Patricio Castillo, Ricardo Dalmacci, Roberto Medina, Rodrigo Murray, Rodrigo Ostap, Rosa María Bianchi, Vanessa Bauche

Director: Alejandro González Iñárritu

Rating: R

Shattering the rules for how a biographical drama can look and be told, Paul Schrader's Mishima rejects the usual character study template in favor of a much more abstract attempt to understand a person through their art. Told in fragments that flit between Mishima's early life, dramatizations of his fiction novels, and the final day of his life, the film pieces together what it believes was the core of this person's life. Schrader's script (co-written with his brother Leonard Schrader) traces within Mishima's history a lifelong struggle with perceptions of his own masculinity and authority—as if he spent his every waking moment trying to compensate for a lack that he could hardly articulate. The character's eventual turn towards reactionary beliefs makes logical sense in the film, but remains baffling all the same.

With all of its talk about beauty—enhanced by Philip Glass' opulent musical score, and Eiko Ishioka's breathtaking production design that transforms Mishima's novels into tactile stage productions—the film conceals an incredibly dark heart. Mishima doesn't inspire sympathy so much as he inspires morbid fascination, and it's both a daring and frustrating choice to focus entirely on the character's harmful delusions without room for much else. Still, Schrader has constructed an unforgettable audiovisual experience that lingers long after it's over.

Genre: Drama, History

Actor: Alan Poul, Bandō Mitsugorō X, Chishū Ryū, Eimei Esumi, Go Riju, Haruko Kato, Hideo Fukuhara, Hiroshi Katsuno, Hiroshi Mikami, Hisako Manda, Jun Negami, Junkichi Orimoto, Ken Ogata, Kenji Sawada, Koichi Sato, Kunihiko Ida, Masahiko Sakata, Masato Aizawa, Masayuki Shionoya, Miki Takakura, Minoru Hodaka, Mitsuru Hirata, Naoko Ohtani, Naomi Oki, Naoya Makoto, Reisen Ri, Roy Scheider, Ryō Ikebe, Sachiko Hidari, Setsuko Karasuma, Toshiyuki Nagashima, Yasuaki Kurata, Yasuhiro Arai, Yuki Kitazume

Director: Paul Schrader

Rating: R

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

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

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