105 Best Challenging Movies On Itunes (Page 6)

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.

, 2011

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

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: Benoit Magimel, Cécile Guilbert, Marc Susini, Montse Triola, Sergi Lopez

Director: Albert Serra

Surreal, off-putting, and extremely disturbing, Infinity Pool plays with the concepts of cloning and the death penalty to craft an examination on colonial tourism. It’s a thematically rich horror film, with hazy neon-lit sex scenes and absolutely terrible behavior, enabled by their wealth and advanced technology that could have been put to better use. Mia Goth, in particular, is strikingly unhinged, as Gabi taunts and lures James into bigger and more terrible crimes, crimes that he can only pay off with the wealth of his father-in-law. And Alexander Skarsgård as James believably gets sucked into this extremely libertine lifestyle, fuelled by the nepotistic anxiety of not living up to his own potential. The film presents a scary notion that pushed by wealth and playground tactics, one will willingly kill their own conscience, again and again, to belong to their cohort.

Genre: Horror, Science Fiction, Thriller

Actor: Alexander Skarsgård, Amanda Brugel, Amar Bukvić, Caroline Boulton, Cleopatra Coleman, Géza Kovács, Jalil Lespert, Jeff Ricketts, John Ralston, Mia Goth, Roderick Hill, Romina Tonković, Thomas Kretschmann

Director: Brandon Cronenberg

Rating: R

Great Freedom is not an easy watch. Apart from the quiet stretches of time and the claustrophobic confines of its prison setting, it also has its lead, Hans Hoffman (played with delicate force by Franz Rogowski) imprisoned again and again and again, unjustly treated like dirt by both his warden and fellow inmates.

But as a Jewish gay man who has lived through the war, Hans is no stranger to these trappings. As such, he takes each day as it comes, open to love, pleasure, and friendship, or at least the potential of these, despite the circumstances. And so Great Freedom is also hopeful and romantic, glimmering with the human tendency to not just survive but to live. Slow but compelling, subdued but powerful, Great Freedom is an affecting balancing act that's well worth watching. 

Genre: Crime, Drama, Romance, War

Actor: Andreas Patton, Anton von Lucke, Fabian Stumm, Franz Rogowski, Georg Friedrich, Thomas Prenn, Thomas Stecher

Director: Sebastian Meise

Based on the short story “God Sees the Truth, But Waits” by Leo Tolstoy, The Woman Who Left is a film about people with nowhere to go. Set in 1990s Philippines, the film follows Horacia, an ex-convict seeking revenge on her former lover who masterminded her unjust 30-year imprisonment. Along the way, she meets various people—a hunchback balut vendor, vagabonds, and an epileptic trans woman, among others—all downtrodden in their own unique ways and united only by their nightly wanderings, with whom Horacia’s true nature is revealed and reconfigured with every encounter.

Lav Diaz’s signature slow cinema minimalism and sharp chiaroscuro lighting allow for a meditative experience, further enhancing the film’s immersive quality. Despite its bleak atmosphere, The Woman Who Left remains hopeful amidst moral quandaries, where things eventually fall into their rightful place, albeit in unexpected ways.

Genre: Drama

Actor: Charo Santos-Concio, John Lloyd Cruz, Kakai Bautista, Lao Rodriguez, Mae Paner, Michael De Mesa, Nonie Buencamino, Shamaine Buencamino

Director: Lav Diaz

This gripping legal drama is based on a case we still don’t know the truth of — which might make it seem like a pointless exercise, were it not for the fact that it’s infectiously fascinated by greater questions than whether wealthy socialite Claus von Bülow (Jeremy Irons) really did attempt to kill wife Sunny (Glenn Close), who was left comatose by the mysterious event. After being convicted, Claus recruited for his appeal then-hotshot lawyer Alan Dershowitz (Ron Silver), now better known for personal allegations and his defense of men even more nefarious than Claus. Reversal follows the tricky legal argument-crafting process, embedding us with Dershowitz’s elite team as they meticulously comb through the prosecution’s theory to find the hairline crack they need to break the case open.

But why go to all this effort to exonerate an unlikeable and frustratingly enigmatic man like Claus, whom Dershowitz apparently doesn’t even believe himself? While we’re morbidly fascinated by unknowable cases like this, it’s the passion of the defense that’s really puzzling — something Reversal shrewdly gets as it wrestles with the ethical arguments for and against Dershowitz’s involvement, making for a pre-courtroom drama whose power extends beyond that of the particular case it documents.

Genre: Drama

Actor: Alan Pottinger, Annabella Sciorra, Bill Camp, Brian Delate, Bruno Eyron, Christine Baranski, Christine Dunford, Constance Shulman, Ericka Klein, Felicity Huffman, Fisher Stevens, Frederick Neumann, Glenn Close, Gordon Joseph Weiss, Jack Gilpin, Jad Mager, JD Cullum, Jeremy Irons, Jessika Cardinahl, Johann Carlo, Julie Hagerty, Keith Reddin, Larry Sherman, Leo Leyden, LisaGay Hamilton, Malachy McCourt, Mitchell Whitfield, Redman Maxfield, Ron Silver, Stephen Mailer, Tom Wright, Uta Hagen

Director: Barbet Schroeder

At first glance, The Madness of King George seemed like a history lesson about King George III. Like plenty of British royalty dramas, the film has all the opulent trappings in its sets and costumes, as well as some of the best actors from the British isles. However, unlike other depictions of the monarchy, the film depicts the king not as a benevolent ruler or oppressive tyrant– instead, King George III is terribly human, with his memory failing, being unsettled by loss, and concern over his health, which involves having to look at his urine. But the historical satire, based on the 1991 stage play, still manages to have the same mockery towards the opportunistic court, while still retaining sympathy for the very nobility it mocks, through original playwright Alan Bennett’s adept writing, as well as the excellent performance of the stacked ensemble cast.

Genre: Comedy, Drama, History

Actor: Adrian Scarborough, Alan Bennett, Amanda Donohoe, Anthony Calf, Barry Stanton, Caroline Harker, Charlotte Curley, Clive Brunt, Colin McPhillamy, Cyril Shaps, David Leon, Dermot Keaney, Geoffrey Palmer, Helen Mirren, Iain Mitchell, Ian Holm, Janine Duvitski, Jeremy Child, Jim Carter, Joanna Hall, John Wood, Julian Rhind-Tutt, Julian Wadham, Michael Grandage, Nicholas Irons, Nicholas Selby, Nick Sampson, Nigel Hawthorne, Paul Corrigan, Peter Woodthorpe, Robert Swann, Roger Ashton-Griffiths, Roger Hammond, Rupert Everett, Rupert Graves, Selina Cadell, Struan Rodger

Director: Nicholas Hytner

Rating: PG-13

Classroom chatter and inside jokes; the rhythmic routine of class, band practice, and communal mealtime; colorful paints and a keen Shakespeare play; paperback books, pages bookmarked with dogears. These are the precious, ordinary wonders of Headfort, a preparatory boarding school in Ireland. 

School Life observes Amanda and John Leyden, who have each taught at Headfort for over four decades. As they both near retirement, so too looms the promise of a tranquil retreat into the countryside—and questions of what they leave behind in their school, their classrooms, and their students. Idyllic and gentle, this documentary offers a brief but meaningful look into the school lives of bright children indelibly influenced by their earliest mentors.

Genre: Documentary

Director: David Rane, Neasa Ní Chianáin

Rating: PG-13

During wartime, war supersedes everything, including love. Wartime would have people ending relationships, forgoing potential dates, and seducing enemies to lead them to downfall, all in order to win, but sometimes, this rarely goes as planned. Lust, Caution is one such story, with the novella’s emotional repression making it a great match for director Ang Lee, main actor Tony Leung Chiu-wai as Japanese informant, and main actress Tang Wei, who made her breakthrough here. It’s not an easy watch. There are moments that falter and the film is a tad too long. But the smoldering stares shared by the two leads, with the lush production design and the beautiful direction, makes Lust, Caution a difficult contemplation of love and sexuality as Wang’s, and the nation’s, double-edged sword.

Genre: Action, Drama, Romance, Thriller

Actor: Akiko Takeshita, Anupam Kher, Cheng Yu-Lai, Chih-ying Chu, Chin Ka-lok, Chung Hua Tou, Hayato Fujiki, He Saifei, Jacqueline Zhu Zhi-Ying, Joan Chen, Johnson Yuen, Johnson Yuen Tak-Cheung, Kar Lok Chin, Ko Yu-Luen, Lawrence Ko, Lawrence Ko Yu-Luen, Lee Hom Wang, Leehom Wang, Lisa Lu, Liu Jie, Saifei He, Tang Wei, Tony Chiu-Wai Leung, Tony Leung Chiu-Wai, Tou Chung-Hua, Tou Tsung-Hua, Ven Kao, Vince Kao, Wang Lin, Wei Tang, Yan Su, Ying-hsien Kao

Director: Ang Lee

Rating: NC-17

The only Kundera film adaptation frankly hasn’t disproven that the source novel is unfilmable, but The Unbearable Lightness of Being is a pretty decent attempt. While Kundera’s meditations aren’t tackled in full depth, director Philip Kaufman manages to retain enough of the novel’s images to rein in the unwieldy plot, such as Sabina with the mirror, Tereza’s nightmare of naked women, their photography around Sabina’s studio and the black-and-white moment of Prague Spring, where editor Walter Murch adeptly inserts Tereza and Tomas within the historical footage. These images, along with the excellent cast, keep the wistful feeling that haunts Kundera’s novel.

Genre: Drama, Romance

Actor: Anne Lonnberg, Bruce Myers, Clovis Cornillac, Consuelo De Haviland, Daniel Day-Lewis, Daniel Olbrychski, Derek de Lint, Donald Moffat, Erland Josephson, Jacques Ciron, Juliette Binoche, László Szabó, Lena Olin, Leon Lissek, Pascale Kalensky, Pavel Landovský, Pavel Slabý, Stellan Skarsgård, Tomasz Borkowy, Vladimír Valenta

Director: Philip Kaufman

Rating: R

This difficult movie is about a seventeen-year-old from the U.S. underclass who has to deal with an unplanned pregnancy. Autumn is creative, reserved, and quiet, but those are not qualities that her environment in rural Pennsylvania seems to value. On the opposite, she is surrounded by threats, including disturbing step-father and boss characters. 

Dangers escalate as Autumn decides to travel to New York to have an abortion. Never Rarely Sometimes Always is about unplanned pregnancies as much as it is about just how dangerous it is to be a teenage girl living in America.

Genre: Drama

Actor: Amy Tribbey, Brian Altemus, Carolina Espiro, Christian Clements, David Buneta, Denise Pillott, Drew Seltzer, Eliazar Jimenez, Lizbeth MacKay, Mia Dillon, Ryan Eggold, Salem Murphy, Sam Dugger, Sharon Van Etten, Sidney Flanigan, Sipiwe Moyo, Talia Ryder, Théodore Pellerin, Théodore Pellerin

Director: Eliza Hittman

Rating: PG-13

While primarily a showcase of endoscopic footage of various surgeries in different hospitals throughout Paris—which should already be enough to either make you queasy or inspire introspection into the fragility of our lives—this singular, experimental documentary places all this bloodshed in the context of the mundanity of the medical profession. Much of the film is taken up by muted conversation from the surgeons and footage of elderly patients wandering around, creating an even more surreal look into the lack of support these hospitals receive. It's far more abstract than it is educational, but its commitment to getting its hands dirty makes it an unforgettable experience.

Genre: Documentary

Director: Lucien Castaing-Taylor, Véréna Paravel

Even with its haphazard construction and occasionally unnecessary and corny flourishes (what's with all the mellowed-out covers of pop songs?), there's a sense of intense, sincere pride and joy that shines through Every Body's many testimonials. Intersex people are barely represented whether in media or in legislation, and countless people still have very little understanding of what intersex is. But while this subject is usually viewed as uncomfortable—and this documentary definitely doesn't hold back in explaining the various ways intersex people are mutilated and mentally abused just to force them to conform to the gender binary—the film grounds everything by showing us how its main characters are as ordinary, creative, and full of good humor as the rest of us. So as Every Body skips through various aspects of the intersex experience, even its disorganization takes on the charm of a simple chat with friends. And either way, the discussions held here are the stuff of real courage—demanding our attention and earning our respect.

Genre: Documentary

Actor: Alicia Roth Weigel, Julie Cohen, River Gallo, Sean Saifa Wall, Steven Crowder

Director: Julie Cohen

Blue Bayou is a powerful film about a Korean-American man threatened with deportation from the only country he has ever known. Antonio LeBlanc is a hard-working mechanic living in a small town in Louisiana with his wife, Kathy, and their young daughter Jessie. Blue Bayou is a beautifully made film with compelling performances from Chon, Vikander, and the rest of the cast. The film is heartbreaking and hopeful, offering a powerful message about the importance of family and belonging. Justin Chon's direction is assured and confident as he captures the beauty of the Louisiana Bayou and aptly conveys Antonio's isolation and loneliness. He brings a strong sense of empathy and humanity to the material.

Genre: Drama

Actor: Alicia Vikander, Altonio Jackson, Emory Cohen, Geraldine Singer, Jeremy Sande, Jim Gleason, Justin Chon, Linh Dan Pham, Mark O'Brien, Martin Bats Bradford, Randy Austin, Renell Gibbs, Rhonda Johnson Dents, Susan McPhail, Sydney Kowalske, Sylvia Grace Crim, Tyler Henry, Vondie Curtis-Hall

Director: Justin Chon

From The Babadook director Jennifer Kent comes another horror, although this one is more about the horrors of humanity. Set in 1825 Tasmania, The Nightingale follows Irish settler Clare as she seeks bloody revenge on the monsters who wronged her and her family. She teams up with an Aboriginal guide named Billy to accomplish her goal.

Because of its often violent and disturbing tone (the film is rated R for its potentially triggering scenes), The Nightingale understandably polarized audiences upon its release. But it's also an excellent conversation piece, best watched with friends or anyone up for a discussion-filled movie night.

Genre: Adventure, Drama, History, Thriller

Actor: Aisling Franciosi, Alan Faulkner, Anthony Phelan, Baykali Ganambarr, Ben McIvor, Charlie Jampijinpa Brown, Charlie Shotwell, Christopher Stollery, Damon Herriman, Eloise Winestock, Ewen Leslie, Harry Greenwood, Huw Higginson, James O'Connell, Luke Carroll, Maggie Blinco, Magnolia Maymuru, Matthew Sunderland, Michael Sheasby, Nathaniel Dean, Sam Claflin, Sam Smith

Director: Jennifer Kent

Rating: R