497 Best Challenging Movies to Watch (Page 6)

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.

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76. The Curse, 2023

That The Curse is squirm-inducingly awkward won’t be news to anyone who’s watched a Nathan Fielder show before, but TV’s king of cringe digs his heels in on that approach here. The Curse chronicles the making of another show: HGTV’s inelegantly named “Flipanthropy,” which follows Fielder’s Asher and wife Whitney Siegel (Emma Stone) as they perform (the operative word) good deeds in a struggling New Mexico town. Flipanthropy is also a means through which the well-to-do white couple can shill the eco-friendly homes they’re gentrifying the town with — a galling conflict of interest that plays as a running satire of TV. The uneasy tension between what the Siegels say they want to do versus what they actually do is the heart of the show. In true Fielder fashion, their hypocrisy is revealed through excruciatingly awkward, tortuously long scenes takes, such as the one that gives the show its title (the socially inept Asher angers a little girl, who puts a curse on him). This scene is also an example of the insane left takes The Curse constantly takes, which speak to Fielder’s ability to make his shows feel like they’re falling apart all while building to towering complexity. Suffice it to say, there’s nothing else like this on TV.

Genre: Comedy, Drama

Actor: Benny Safdie, Emma Stone, Nathan Fielder

Rating: TV-MA

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77. Papicha, 2019

Set against the backdrop of the Algerian Civil War in the 1990s, the film follows Nedjma, a young fashion student, as she navigates the challenges of pursuing her dreams while living under strict societal and religious constraints. Gripping and emotionally charged, the film paints a vivid picture of the oppressive climate and the courageous women who refuse to be silenced. The performances are outstanding, particularly Lyna Khoudri's portrayal of Nedjma, who brings a compelling blend of vulnerability and determination to her character. Director Mounia Meddour's storytelling is powerful and thought-provoking, shining a light on the resilience of women in the face of adversity and the importance of artistic expression as a form of resistance.

Genre: Drama

Actor: Ahmed Benaissa, Aida Guechoud, Amira Hilda Douaouda, Khaled Benaissa, Lyna Khoudri, Nadia Kaci, Samir Elhakim, Shirine Boutella, Yasin Houicha, Zahra Doumandji

Director: Mounia Meddour

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78. Nymphomaniac: Vol. I, 2013

Danish writer-director Lars von Trier concludes his so-called Depression trilogy with the two parts of Nymphomaniac, an elaborate retelling of the life of a young woman (played by Stacy Martin and then, by Charlotte Gainsbourg) lived from one libidinous pleasure to another. The film's elaborate subplots have a life of their own and flashbacks often take center stage in Joe's auto-narration. Nymphomaniac I introduces the audience to adolescence and early adulthood, through disappointments, adultery, death drive, and extreme ambivalence. Joe's process of self-actualization seems contested and inspiring at the same time, and Gainsbourg is really given the screen time to shine; even more so than in Trier's previous psycho-social drama, Antichrist. Typically for the rich treasury of cultural references, Bach, Edgar Allan Poe, and Fibonacci play crucial parts in reconstructing the symbolic planes in Joe's story. Oh, and Part One opens with Rammstein's "Führe mich", which in itself is an perfectly valid reason to give it a go.

Genre: Drama

Actor: Ananya Berg, Anders Hove, Andreas Grötzinger, Charlie Hawkins, Charlotte Gainsbourg, Christian Slater, Christoph Jöde, Christoph Schechinger, Clayton Nemrow, Connie Nielsen, Cyron Melville, David Halina, George Dawson, Hugo Speer, James Northcote, Jamie Bell, Jeff Burrell, Jens Albinus, Jesper Christensen, Jesse Inman, Johannes Kienast, Jonas Baeck, Maja Arsovic, Markus Tomczyk, Mia Goth, Michael Pas, Nicolas Bro, Peter Gilbert Cotton, Saskia Reeves, Shia LaBeouf, Simon Böer, Sofie Kasten, Sophie Kennedy Clark, Stacy Martin, Stellan Skarsgård, Tomas Spencer, Uma Thurman, Willem Dafoe

Director: Lars von Trier

Rating: Not Rated, NR

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79. I'm Not There, 2007

I’m Not There is an unusual biopic in that it never refers to its subject, Bob Dylan, by name. Instead, Todd Haynes’ portrait of the singer mimics his constant reinvention by casting six separate actors to play as many reincarnations of the same soul. It’s an ingenious spin on a usually stale genre, one that liberates the film from the humdrum restrictions of a literal retelling of Dylan's life.

If there’s anyone who warrants such an inventive approach to biography, it’s Dylan, whose public and private personas are so numerous that it’s only by angling six different mirrors at him that Haynes can hope to catch some of his essence. Impressionistic editing toggles freely between these vignettes, each visually distinct: from the 11-year-old Woody Guthrie-obsessive (Marcus Carl Franklin) and the black-and-white Super 16mm-shot poet (Ben Whishaw) to the aging cowboy outlaw (Richard Gere), all by way of Christian Bale, Heath Ledger, and Cate Blanchett’s incarnations. To be sure, this is a somewhat challenging film, reflecting, in places, the enigmatic surrealism of Dylan’s lyrics and his refusal to be pinned down to one thing. But, as Blanchett’s embodiment says, “Mystery is a traditional fact,” and that’s no more true than of Dylan, making Haynes’ film a fascinatingly fitting spiritual biopic.

Genre: Drama, Music

Actor: Al Vandecruys, Alison Folland, Andrew Shaver, Andrew Simms, Angela Galuppo, Arthur Holden, Ben Whishaw, Benz Antoine, Bill Croft, Bob Dylan, Brett Watson, Bruce Greenwood, Cate Blanchett, Catherine Colvey, Charlotte Gainsbourg, Christian Bale, Clarice Byrne, Craig Thomas, Daniel Richard Giverin, Danny Blanco Hall, David Cross, David Gow, Dennis St John, Dominic James, Don Francks, Emmanuel Schwartz, Eric Newsome, Eugene Brotto, Fanny La Croix, Garth Gilker, Gordon Masten, Graham Cuthbertson, Greg Kramer, Heath Ledger, Hélèna Laliberté, Holly Uloth, Ivan Freud, Jane Gilchrist, Jane Wheeler, Jason Cavalier, Jean-Loup Yale, Jennifer Rae Westley, Jesse Todd, Jessica Kardos, Jim James, Jodie Resther, Joe Cobden, Joey Burns, John Koensgen, Julianne Moore, Kathleen Fee, Kathryn Kostlivy, Kim Gordon, Kim Roberts, Kris Kristofferson, Kristen Hager, Kyle Gatehouse, Kyle Switzer, Larry Day, Leif Anderson, Leigh Ann Taylor, Lina Roessler, Lisa Bronwyn Moore, Lorne Brass, Maggie Castle, Marcus Carl Franklin, Marie-Julie Rivest, Mark Camacho, Matt Holland, Matthew Boylan, Matthew Harbour, Max Walker, Melantha Blackthorne, Michelle Williams, Mike Caruso, Nathalie Girard, Noel Burton, Patrick Costello, Paul Cagelet, Paul Johnston, Paul Spence, Pauline Little, Peter Friedman, Phyllis Gooden, Pier Paquette, Pierre Leblanc, Pierre-Alexandre Fortin, Richard Gere, Richard Jutras, Richard Robitaille, Richie Havens, Rob Burns, Roc LaFortune, Sharlene Royer, Shaun Balbar, Shawn Baichoo, Steve Godin, Susan Glover, Terry Haig, Thiéry Dubé, Tim Post, Trevor Hayes, Tyrone Benskin, Vito DeFilippo, Wyatt Bowen, Yolonda Ross

Director: Todd Haynes

Rating: R

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80. Godland, 2022

On the one hand, Godland is a film about nature’s unforgiving beauty. Like the photographs the priest Lucas (Elliott Crosset Hove) takes, these quietly superb scenes speak for themselves. The Earth moves in mysterious and harsh ways, and we are but mere specks, organic matter to be folded in and absorbed, in the grand scheme of things. It would’ve worked with just this message alone, but Godland also treads on political ground. Through Lucas, who is Danish, and his travel guide Ragnar (Ingvar Sigurdsson), who is Icelandic, we sense a palpable tension that electrifies the film with a colonial strain. There are layers to their deep aversion (and dependence) on one another, and director Hlynur Pálmason does well to pair this with imagery that is just complex, profound, and packed with meaning.

Genre: Drama

Actor: Elliott Crosset Hove, Ída Mekkín Hlynsdóttir, Ingvar E. Sigurðsson, Jacob Ulrik Lohmann, Vic Carmen Sonne, Waage Sandø

Director: Hlynur Palmason

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81. Don't Let Them Shoot the Kite, 1989

	
Originally a novel inspired by real life incarceration, Don't Let Them Shoot the Kite is actually much more optimistic than a prison stay would seem to be. Much of that lighter mood comes from an outstanding performance– Ozan Bilen, who portrays Barış, the precocious boy that lives in the prison with his mom due to a quirk of Turkish law– but the lighter mood isn’t due to ignoring the prisoners’ reality. Instead, the lightness comes because of understanding that reality fully. Despite the suspicion of the prison guards, and the way the camera makes the prison walls loom, Barış still manages to fuel some hope through straightforward, simple truths unfiltered by the tedium and mores of everyday life, and the fear people grow to learn about. Truth truly comes out of the mouths of babes in this film, and it’s what makes Don't Let Them Shoot the Kite a classic of Turkish cinema.Genre: Drama
Actor: Ayben Erman, Ayla Arslancan, Füsun Demirel, Güzin Özipek, Güzin Özyağcılar, Meral Çetinkaya, Nur Sürer, Nurettin Şen, Ozan Bilen, Özlem Savaş, Rozet Hubeş, Sabriye Kara, Selma Tarcan, Sevim Çalışgir
Director: Tunç Başaran

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82. Brazil, 1985

In the movie Brazil, our hero Sam Lowery (Jonathan Pryce) lives in a dystopian world that relies on the cold productivity grind of machines. He’s in a constant battle between the high-level dominating powers that be and the low-level beatdown scums of society. Saving him from complete misery is a recurring dream he has of a beautiful woman. There, nothing else matters but love, which fills his draining soul and makes his life seem worthwhile.

The way director Terry Gilliam handles a serious matter in such a comedic way is fantastic, and the amount of thought and effort he puts into creating every single bit of existence in this film is mind-boggling. With Brazil, he succeeds in establishing his own style, making a mark for himself in an age when plenty of auteurs compete for mere recognition.

Genre: Comedy, Drama, Science Fiction

Actor: Ann Way, Barbara Hicks, Bill Wallis, Bob Hoskins, Brian Miller, Bryan Pringle, Charles McKeown, David Gant, Derek Deadman, Derrick O'Connor, Don Henderson, Elizabeth Spender, Gorden Kaye, Harold Innocent, Howard Lew Lewis, Ian Holm, Ian Richardson, Jack Purvis, James Coyle, Jim Broadbent, John Flanagan, John Grillo, John Pierce Jones, Jonathan Pryce, Katherine Helmond, Kathryn Pogson, Kim Greist, Michael Palin, Myrtle Devenish, Nigel Planer, Oscar Quitak, Patrick Connor, Peter Vaughan, Ralph Nossek, Ray Cooper, Robert De Niro, Roger Ashton-Griffiths, Russell Keith Grant, Sheila Reid, Simon Jones, Terence Bayler, Terry Gilliam

Director: Terry Gilliam

Rating: R

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83. Bodies, 2023

	
Based on the DC Vertigo comic, Bodies is an intriguing crime thriller with a unique twist – one body, in four separate time periods, being solved simultaneously all at once. While the show is triggered by the same body, the mini-series feels like four separate shows at the same time, marrying the classic Victorian detective mystery, war-torn film noir, and modern day police procedural through post-apocalyptic science fiction. And the four separate detectives take the helm of their respective side of the case, as well as how they deal with the discrimination against them. With four excellent strands to the same mystery, Bodies is an exceptional adaptation that demonstrates how even though details change, some things still remain the same.Genre: Crime, Drama, Mystery, Sci-Fi & Fantasy
Actor: Amaka Okafor, Greta Scacchi, Jacob Fortune-Lloyd, Kyle Soller, Shira Haas, Stephen Graham, Synnøve Karlsen, Tom Mothersdale
Rating: TV-MA

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84. Black Rain, 1989

	
Not to be confused with the American cop thriller with the same name, Shōhei Imamura’s Black Rain is about the atomic bomb, but it’s not really concerned about nuclear warfare. Sure, the film opens with gruesome shots of the day the bomb dropped, not sparing the viewers from the gore and the titular nuclear fallout, that in black and white looks the same. And yes, much of the conflict occurs because of the lingering effects of the radiation. However, Imamura is much more concerned with the way Japanese society had tried to deal with it through going back to tradition– through going through the motions of matchmaking and propriety and social status and through excluding those who suffered directly from the bomb. Black Rain has a singular perspective, one that stands out due to the country’s denial of war crimes.Genre: Drama, History
Actor: Akiji Kobayashi, Etsuko Ichihara, Fujio Tokita, Hideji Ōtaki, Hisako Hara, Kazuko Shirakawa, Kazuo Kitamura, Kenjirou Ishimaru, Masato Yamada, Noboru Mitani, Norihei Miki, Sabu Kawahara, Shoichi Ozawa, Taiji Tonoyama, Takashi Miike, Tamaki Sawa, Toshie Kusunoki, Yoshiko Tanaka
Director: Shōhei Imamura

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85. Through the Olive Trees, 1994

	
We’ve heard of films within a film, but it’s crazy how many layers Through the Olive Trees operates in. Writer-director Abbas Kiarostami completes his metanarrative journey in the Koker trilogy through a slice-of-life comedy about a couple in the periphery of the previous installment And Life Goes On. As the young man Hossein repeats his plea for marriage to Tahereh, casted as his wife, the insistence can be slightly grating, but in doing so, the everyday dealings of the Iranian village hint at what’s underneath– the earthquake from four years ago that still shapes their lives, the socioeconomic and culture barriers, and the mirrored struggle of creating the artistic vision of the film within the film.Genre: Drama
Actor: Abbas Kiarostami, Farhad Kheradmand, Hossein Rezai, Jafar Panahi, Mohammadali Keshavarz, Tahereh Ladanian, Zarifeh Shiva
Director: Abbas Kiarostami

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86. The Underground Railroad, 2021

As is only appropriate for a limited series about such a horrific period in human history, The Underground Railroad isn't meant to be easy viewing. Thanks to uncompromising direction from Barry Jenkins (the director of the Best Picture Oscar winner Moonlight) and unforgettable images from cinematographer James Laxton, this approaches a level of confrontational storytelling that almost seems inappropriate for the comforts of television. But it's essential viewing nonetheless, and Jenkins makes sure to transform this into a much stranger, more thought-provoking tale beyond the brutality of its first episode. The Underground Railroad is speculative fiction: instead of being a historical account of the real-life network of routes to help free African-American slaves, it imagines a literal train that swiftly transports Cora (a powerful Thuso Mbedu) from one dystopian vision of white America to another. With every new setting, Jenkins doesn't just talk about slavery; he talks about how America talks about slavery, and how the stories of these Black slaves are constantly reappropriated by white supremacists.

Genre: Drama, Fantasy, History, Sci-Fi & Fantasy

Actor: Chase W. Dillon, Joel Edgerton, Thuso Mbedu

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87. The Staircase, 2022

The bizarre case of Kathleen Peterson's death, which has yet to be fully resolved to this day, has been the subject of many a media article. The press covered it relentlessly when it all started in 2001, then a critically-acclaimed documentary was released in 2004. This was followed up with a sequel in 2018, and now more than 20 years after the deed, a dramatization has come out in the form of a miniseries. You'd be forgiven for thinking the latter couldn't possibly have anything new to offer, but you would also be wrong. In fact, the series is a masterclass in storytelling. Led by an a-list cast (of which Colin Firth is the absolute standout) and told with such layered depth, The Staircase is a must-watch not just for true crime but for film and TV fans everywhere.

Utilizing time jumps and crafty transitions, The Staircase isn't set at one particular time, which is fitting considering the trial lasted for 16 years. It also isn't centered on just the mystery or the family, but instead is just as interested in the making of the 2004 documentary that introduced (and humanized) the case to an even wider sect of people. If you're looking for a neat ending or some form of satisfying retribution, you won't find it here. But you will be getting an engrossing meditation on truth and its elusiveness

Genre: Crime, Drama

Actor: Colin Firth, Dane DeHaan, Juliette Binoche, Michael Stuhlbarg, Odessa Young, Olivia DeJonge, Parker Posey, Patrick Schwarzenegger, Rosemarie DeWitt, Sophie Turner, Tim Guinee, Toni Collette

Rating: TV-MA

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88. The Perks of Being a Wallflower, 2012

This coming-of-age story based on the bestseller by the same name starts fun but veers towards darker territory. It's about a high-schooler who makes two older friends, played perfectly by Ezra Miller and Emma Watson. But as he gets closer to one of them, his anxieties and past trauma come to the surface. The impressive depth to which the makers of The Perks of Being a Wallflower were able to take it is what elevates it to greatness. It's the perfect mix between easy and challenging. If there is ever such a thing, it's this movie.

Genre: Comedy, Drama

Actor: Adam Hagenbuch, Brian Balzerini, Chelsea Zhang, Dihlon McManne, Dylan McDermott, Emily Marie Callaway, Emma Watson, Erin Wilhelmi, Ezra Miller, Jennifer Enskat, Joan Cusack, Joe Fishel, Johnny Simmons, Jordan Paley, Julia Garner, Kate Walsh, Landon Pigg, Leo Miles Farmerie, Logan Lerman, Mae Whitman, Mark McClain Wilson, Melanie Lynskey, Morgan Wolk, Nicholas Braun, Nina Dobrev, Patrick de Ledebur, Paul Rudd, Reece Thompson, Stacy Chbosky, Stephen Chbosky, Tom Savini, William L. Thomas, Zane Holtz

Director: Stephen Chbosky

Rating: PG-13

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89. The Narco Satanist,

Overseeing drug rings, cult machinations, and human sacrifice under the guise of practicing the religion known as Santeria defined the crimes of Adolfo de Jesús Constanzo in Mexico during the late 1980s. And instead of following one straight recollection, the documentary tells two sides of the case: one from Sara Aldrete and the police and media as everything unfolds. What starts as a disjointed journey to proving Sara's involvement and guilt becomes blurred as the documentary asks the audience to contemplate a different outcome. Does Sara's young age afford her more sympathy? Was the case rushed and mishandled? Did the police (and other powerful people) force the outcome of the case? Watching only the first episode would be a disservice to the broader context and overlooked participants the producers shine a light on.

Genre: Documentary

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90. The Missing Picture, 2013

	
The medium of cinema has been used as a tool for revolution, but so too was it complicit in genocide. That was true of the Khmer Rouge regime, as the remaining footage of the time came entirely from the state, to be used in re-education programs and propaganda to hide the difficult realities caused by the administration. In response, three decades later, documentarian Rithy Panh reclaims the medium, juxtaposing archival footage of Pol Pot’s programs and Cambodia before, with clay figurines formed from his memories. It’s a grim recollection, but The Missing Picture takes back cinema to keep a collective memory that must be preserved.Genre: Animation, Documentary
Actor: Jean-Baptiste Phou, Randal Douc
Director: Rithy Panh

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