473 Best Challenging Movies to Watch (Page 17)

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.

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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Because of our continued interest in living, one would think that human beings would shy away from death, but the opposite seems to be the reality. There’s a certain morbid fascination with violence, to the point that some people are captivated in making it more intense, more sensational, and more dangerous. Just before his groundbreaking second feature, Alejandro Amenábar made his debut around that idea in Thesis. It’s quite meta, of course, with the film about film students studying violence in media pulled into a murder mystery after discovering a snuff film, but Amenábar also sticks quite close to the narrative conventions of the genre, remixing certain tropes and the general knowledge of how such a film would go to heighten the sense of paranoia that Angela (and the audience) feels.

Genre: Drama, Horror, Thriller

Actor: Ana Torrent, Eduardo Noriega, Emiliano Otegui, Fele Martínez, Fele Martínez, José Luis Cuerda, Miguel Picazo, Nieves Herranz, Paco Hernández, Rosa Campillo, Xabier Elorriaga

Director: Alejandro Amenábar, Alejandro Amenábar

Rating: R

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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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Crushes seem much more important when you’re young, and when you and your sibling share one, it easily alters your dynamic, with the jealousy, comparison, and the insecurity it can foster. The Man in the Moon tackles this childhood crush with care. Writer Jenny Wingfield and director Robert Mulligan characterize each kid with consideration befitting their ages, with an understanding of the different priorities they would have with a three year age gap, the feelings they would have, and the misunderstandings they would have with each other. And this all works because of Reese Witherspoon, who even then held a screen presence that made her into a star.

Genre: Drama, Family, Romance

Actor: Bentley Mitchum, Dennis Letts, Emily Warfield, Ernie Lively, Gail Strickland, Jason London, Reese Witherspoon, Sam Waterston, Tess Harper

Director: Robert Mulligan

Rating: PG-13

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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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We’ve seen anthology films with three, four, sometimes even five parts, but Songs from the Second Floor comprises forty six separate vignettes, quickly shifting in and out without any connecting thread inbetween, except for the dull gray color palette. Yet, even as the film abruptly transitions between vignettes, from tanning beds, construction sites, cars, trains, or buildings, writer-director Roy Andersson crafts meticulously framed breakdowns of modern day living, some of which works based on individual experiences, but all coming together as several miniature portraits of how absurd and depressing our lives have become. Songs from the Second Floor is a bold way to return after a twenty five year hiatus.

Genre: Comedy, Drama

Actor: Bengt C.W. Carlsson, Lars Nordh, Rolando Núñez, Sandy Mansson, Stefan Larsson, Sten Andersson, Torbjörn Fahlström

Director: Roy Andersson

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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, Sara Roch

Director: Paco Plaza

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A devastating depiction of sexual addiction, featuring Michael Fassbender in one of the most remarkable acting displays of the entire year. His performance is nearly matched by Carey Mulligan as his wayward sister, whose intrusion into his lifestyle sets the central conflict of the story in motion. To sex what Requiem for a Dream was to drugs, this is NOT a film to be viewed in any sort of mixed company (note the NC-17 rating). Director and renowned British artist Steve McQueen continues his ascension toward filmmaking royalty, in follow-up to his extraordinary 2008 feature Hunger (also starring Fassbender).

Genre: Drama

Actor: Alex Manette, Amy Hargreaves, Anna Rose Hopkins, Calamity Chang, Carey Mulligan, Carl Low, Charisse Bellante, Chazz Menendez, Deedee Luxe, Elizabeth Masucci, Hannah Ware, Jake Siciliano, James Badge Dale, Loren Omer, Lucy Walters, Mari-Ange Ramirez, Marta Milans, Michael Fassbender, Nicole Beharie, Rachel Farrar, Robert Montano

Director: Steve McQueen

Rating: NC-17

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It doesn’t feel quite right to call Pacifiction a political thriller — at 2 hours 45 minutes and with an unhurried, dreamlike pace, it’s hardly the adrenaline rush that that categorization suggests. But Albert Serra’s film is still suffused with all the paranoia and intrigue that the genre promises, just at a slower burn. The specters of colonialism and nuclear apocalypse hang low over the movie, which is set in an idyllic Tahiti, where Benoît Magimel’s Monsieur De Roller is stationed as France’s outgoing High Commissioner, a bureaucratic relic of the country’s imperialist history. As shady figures and strange rumors about a military submarine begin to arrive on the island, a paranoid De Roller struggles to exert political control — and, in the process, seems to lose some of his own sanity. With an ethereal score, defiantly murky plot, hallucinatory cinematography, and some of humanity’s greatest horrors hanging over it like a pall, Pacifiction feels like a fever dream in the truest sense.

Genre: Drama, Thriller

Actor: Alexandre Melo, Baptiste Pinteaux, Benoit Magimel, Cécile Guilbert, Lluís Serrat, Marc Susini, Montse Triola, Pahoa Mahagafanau, Sergi Lopez

Director: Albert Serra

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