330 Best Challenging Movies to Watch (Page 13)

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.

Comparisons are easy between friends and within peer groups, but the comparison that is most immediate is that between you and your sibling, especially when they wound up more successful than you are. Hilary and Jackie captures that experience between two real-life musical sisters, but the comparison is so much more difficult as Jackie shot to cellist superstardom, even with under the same musical beginnings as her less known sister Hilary. It’s flawed, but it’s deeply personal, diving into their shared anxieties from two different lives, and it’s surprisingly well-rounded, perfectly halved between the sisters’ perspectives led excellently by Rachel Griffiths and Emily Watson. Hilary and Jackie is not comfortable to watch, especially during Jackie’s later years, but it’s a daring portrait of a difficult, but still loving, sibling relationship.

Genre: Drama, Music

Actor: Anthony Smee, Bill Paterson, Carla Mendonça, Celia Imrie, Charles Dance, David Morrissey, David Shimwell, Delia Lindsay, Emily Watson, Grace Chatto, James Frain, Jon Rumney, Keylee Jade Flanders, Kika Mirylees, Linda Spurrier, Maggie McCarthy, Nick Haverson, Nyree Dawn Porter, Rachel Griffiths, Robert Rietti, Rupert Penry-Jones, Vernon Dobtcheff

Director: Anand Tucker

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, 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

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From the sheer size of Frederick Wiseman's documentaries (both in length and scope), it should be clear that his goal isn't necessarily to have us retain every piece of information he gives us in all of this film's board meetings and press conferences. This is a film interested in the macro view of how a city works, and Wiseman's attention to detail even in his old age (he's 94 at the time of writing this) is truly inspiring for any aspiring documentarian. City Hall doesn't necessarily tell us anything we might not already know about the coordination between a local government unit and its constituents and citizens, but Wiseman gets us to think of the grand design of it all—which is both wondrous and horrifying to behold.

Genre: Documentary

Actor: Marty Walsh

Director: Frederick Wiseman

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Slow, contemplative, but captivating, Baraka uses no narration, dialogue, or text to connect its images. The documentary stitches together shots with different subjects from different locations around the world. At first, it seems very peaceful—gorgeous, high-definition shots of nature paired with a soothing, resonant score that lulls you into hypnosis—but as the film progresses, director and cinematographer Ron Fricke presents more scenes with people, from the cities to the countryside, to places rarely documented on film. Depending on how you look at it, Baraka will either feel like just a compilation of screensavers or a profound meditation on how intrinsically connected everything is. It’s totally breathtaking either way.

Genre: Documentary, Drama

Director: Ron Fricke

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Demian Bichir was nominated for an Oscar for his role in this movie where he plays an illegal immigrant and father. You might be wondering "who is that?", but trust me you won't after watching this movie. The kindness, complexity, and authenticity he brings to this story are unparalleled.

A Better Life is about the illegal immigrant experience, about the line between the fear of being caught and the aspiration for a better future. It's an excellent and important movie. 

Genre: Drama

Actor: Abraham Belaga, Bobby Soto, Brigitte Sy, Carlos Linares, Chelsea Rendon, Demián Bichir, Dolores Heredia, Eddie 'Piolin' Sotelo, Eddie 'Piolin' Sotelo, Fayçal Safi, Francois Favrat, Gabriel Chavarria, Guillaume Canet, Isabella Rae Thomas, Joaquín Cosío, José Julián, Leila Bekhti, Nancy Lenehan, Nicolas Abraham, Slimane Khettabi, Tim Griffin

Director: Cedric Kahn, Chris Weitz

Rating: PG-13

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In Waltz with Bashir, director Ari Folman grapples with the trauma and dehumanization of war by examining the role he played in the 1982 Invasion of Lebanon. But his memories are fractured, so in an attempt to piece them back together, he visits his comrades and has them recall the events for him. The result is both poignant and painful, a horrific tell-all of what happens on both sides of the battleground. The film is a documentary, chillingly honest and straightforward, but it's also an animation gem that continues the legacy that Persepolis started and Flee continues. By combining the harshness of war with the lightness of animation, all three films effectively deliver their anti-war message with a much-needed human and personal touch. 

Genre: Animation, Documentary, Drama, War

Actor: Ari Folman, Mickey Leon, Ori Sivan, Ron Ben-Yishai, Yehezkel Lazarov

Director: Ari Folman

Rating: R

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An eye-opening 1989 American documentary that boldly explores the experiences of Black gay men in America. Directed by Marlon Riggs, this film challenges societal norms and sheds light on the intersections of race, sexuality, and identity. Through a mix of personal testimonies, poetry, and distinctive visuals, Tongues Untied captures the struggles and resilience of its subjects, offering a raw and honest portrayal of their lives. Riggs' poetic approach and unflinching storytelling create an immersive experience that will leave a lasting impact. The film confronts issues of homophobia, racism, and social exclusion but also celebrates the strength and beauty of self-expression.

Genre: Documentary, Drama

Actor: Eddie Murphy, Marlon Riggs, Michael Bell, Willi Ninja

Director: Marlon Riggs

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Directed by Todd Haynes (I’m Not There, Carol), The Velvet Underground takes an avant-garde approach to tell the story of the 1960s rock band. Like their music, nothing about this documentary is linear and expected. Screens are split to show two different things at once, seemingly unrelated clips are stitched to create a patchwork of feelings, and strobes of light flash multiple times onscreen. It's like an art installation come to life.

The film is dynamic and dazzling, infused with the same underground atmosphere as their early performances. If you’re looking to know more about the band, this film might not be for you. But if you’re looking to experience the band, to feel and see and hear what it was like to catch them at their peak, then this is for you.

Genre: Documentary, Drama, Music

Actor: Allen Ginsberg, Amy Taubin, Andy Warhol, Bill Graham, Billy Name, Cass Elliot, Danny Fields, David Bowie, Frank Zappa, Jackson Browne, John Cale, John Waters, Jonas Mekas, Jonathan Richman, Lou Reed, Marian Zazeela, Mary Woronov, Maureen Tucker, Nico, Sterling Morrison, Tony Conrad

Director: Todd Haynes

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Consisting almost entirely of a single camera angle and long stretches of either silence or mundane conversation, The Plains makes for a particularly challenging—but incredibly unique—example of slow cinema. While its premise may seem almost too minimalist for its own good, the way the film is set up immediately draws us toward how distant people in the present day can be to each other despite our urbanized society. Stuck in this car with these two characters, one becomes hyperaware of how things are both moving too quickly and too slowly, and how so much of life is made up of the in-between moments. The film's fiction elements eventually break the docudrama illusion a little too bluntly (mainly through some suspiciously structured dialogue), but by then one should be too invested to want to get off.

Genre: Documentary, Drama

Actor: Andrew Rakowski, Cheri LeCornu, David Easteal, Inga Rakowski

Director: David Easteal

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Meditative, slow, and peppered with mysticism and subtle humour, Syndromes and a Century is a truly unique Thai drama. With a male and female doctor as the central protagonists, the story is split into two settings, in different hospitals and 40 years apart. This is not a plot-driven movie by any means. Patiently paced scenes weave together the protagonists’ memories with their current lives, in a hypnotic thread that touches on Buddhist themes as it explores the timeless human experiences of love, relationships, illness, and death.

The movie was originally intended to be a tribute to the parents of writer and director Apichatpong Weerasethakul, himself the son of physicians who worked in a hospital. Though he went on to claim that the movie took a different path eventually, it does recall the enigmatic spirit and ethereal quality of childhood memories. Despite—or maybe thanks to—the absence of narrative, Syndromes and a Century remains a beguiling watch from start to finish.

Genre: Drama, Romance

Actor: Jaruchai Iamaram, Jenjira Pongpas, Nantarat Sawaddikul, Sakda Kaewbuadee, Sophon Pukanok

Director: Apichatpong Weerasethakul

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At two hours and nearly 30 minutes, Stonewalling is quite long. The third film from spouses Ryuji Otsuka and Huang Ji takes place in slow, slice-of-life moments, centered around a female lead that mostly doesn’t actively make choices for her own life, so it can feel frustrating to watch. But as the film unfolds, Lynn’s passivity turns out to be the tragically familiar surrender of today’s working class. Lynn tries to make choices to pay out her mother’s debt, to ensure that she’s not indebted herself, through jobs that commodify her youth, her beauty, and even her body, but each move consequently limits her next options. She tries to bargain for other solutions, but it turns out these solutions were never there in the first place. All she can do is quietly adapt, with each failed promise culminating into a baby’s cry.

Genre: Drama

Actor: Cui Chu, Huang Xiaoxiong, Liu Long, Xiao Zilong, Yao Honggui

Director: Huang Ji, Ryuji Otsuka

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Remember the creepy blind nun from the Spanish horror film Veronica? While many nun-related horror films have nuns as its horror element, this time it’s the nun that gets spooked in Sister Death. The new release expands on her backstory, taking the story back in history, in her start as a novitiate in the former convent, a location that’s been changed after the terrors inflicted towards the nuns during the Spanish Civil War. While the film doesn’t delve that deeply, focusing instead on the slowly building up the film’s terror, there is something here about the hidden violence and covered-up trauma that still haunt the Catholic church in Spain, especially to those that have taken vows. Director Paco Plaza meticulously frames each terrific sequence with the isolating doubt in one’s faith that Narcisa experiences.

Genre: Drama, Horror

Actor: Almudena Amor, Antonio Duque, Arantza Vélez, Aria Bedmar, Chelo Vivares, Consuelo Trujillo, Luisa Merelas, Maru Valdivielso, Olimpia Roch, Sandra Escacena

Director: Paco Plaza

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