321 Best Challenging Movies to Watch (Page 8)

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

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This is Kristen Stewart’s proof that she is more than a lip-biting, vampire-loving teenager. Reactive and emotive, she will not disappoint you here. Rather, expect an electrifying and exceptional performance. Paired with Payman Moaadi, they both make of this work an emotionally poignant movie that questions the notion of freedom in the unlikeliest of places: Guantanamo Bay.

Genre: Drama

Actor: Cory Michael Smith, Daniel Leavitt, J. J. Soria, John Carroll Lynch, Joseph Julian Soria, Julia Duffy, Kristen Stewart, Kyle Bornheimer, Ladell Preston, Lane Garrison, Marco Khan, Nawal Bengholam, Payman Maadi, Peyman Maadi, Peyman Moaadi, SerDarius Blain, Tara Holt, Yousuf Azami

Director: Peter Sattler

Rating: R

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

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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

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Focusing squarely on two families and a select few health workers, The First Wave gets intimate access to the fears and anxieties of individuals trying to contend with the effects of the initial outbreak of the coronavirus in New York. That these characters also tend to belong to already vulnerable sectors in the United States isn't a superfluous detail—as director Matthew Heineman illustrates (without the use of detached talking heads interviews) how proper responses to a global pandemic like this one are still hampered by capitalist interests, and racist and xenophobic institutions built into American society. All of these obstacles make every setback and every moment of progress in these characters' lives feel absolutely crucial, making for an emotionally overwhelming experience.

Genre: Documentary, History

Actor: Al Sharpton, Andrew Cuomo

Director: Matthew Heineman

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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

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, 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, Razvan Popescu, Sam Douglas, Sarah Bauerett, Somiko Singha-Sila, Songha Choi, Sophie Kauer, Sydney Lemmon, Sylvia Flote, Tamaki Steinert, Teresa Philomena Schild, Tilla Kratochwil, Vincent Riotta, Vivian Full, Xenia Assenza, Zethphan Smith-Gneist

Director: Todd Field

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There’s no easy way to talk about racism – it’s a nebulous set of ideas that shift and change and manifests in numerous ways that many people can’t even identify as racism because of how prevalent it is. But Dr. Ibram X. Kendi has been able to write down a fairly comprehensive narrative that outlines key historical moments that shaped the world’s concept of race and Blackness, and this narrative is brought to the screen through vivid animations and strategic sequencing by director Roger Ross Williams in new Netflix release Stamped from the Beginning. It’s a provocative, passionate investigation, and it’s one that should be required viewing.

Genre: Animation, Documentary

Actor: Alexa Rachelle Jennings, Angela Davis, Honorée Fanonne Jeffers, Ibram X. Kendi, Jennifer L. Morgan, Julian Joseph, Rafa Marinho

Director: Roger Ross Williams

Rating: R

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A foreign film on par with City of God, and carrying its heritage of naturalistic performances and raw stories. Sin Nombre will take you into a world filled with gut wrenching violence, heart-breaking loss, and non-stop suspense. And while definitely a tough watch, it reports the horrors of immigration with humane and sometimes hopeful outlook. The profound and epic redemption in this movie will leave you thinking about it for days.

Genre: Action, Crime, Drama, Thriller

Actor: Édgar Flores, Benny Emmanuel, Catalina López, Damayanti Quintanar, Diana García, Diana García, Edgar Flores, Felipe Castro, Gabino Rodríguez, Gerardo Taracena, Guillermo Villegas, Héctor Jiménez, Harold Torres, Héctor Jiménez, Juan Pablo Arias Barron, Karla Cecilia Alvarado, Kristian Ferrer, Kristyan Ferrer, Leonardo Alonso, Lilibeth Flores, Luis Fernando Peña, Luis Fernando Peña, Marcela Feregrino, Marcela Macias, Marco Antonio Aguirre, Noé Hernández, Paulina Gaitán, Paulina Gaitan, Tenoch Huerta, Tenoch Huerta Mejía

Director: Cary Fukunaga, Cary Joji Fukunaga

Rating: R

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