502 Best Challenging Movies to Watch (Page 24)

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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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, 2002

Being released just a year after 9/11, we weren’t expecting The Quiet American to be critical about America’s intervention in the Vietnam War– the original novel was criticized by the country in its initial release, and the previous 1958 film adaptation revamped the entire story for an anti-communist message. Still, while the film could have expanded on Phuong’s perspective, The Quiet American is well made and surprisingly faithful to the book– willing to delve into author Graham Greene’s cautionary tale on exceptionalism and acknowledging how his prediction has happened in reality, all easily understood through the simple, yet effective metaphor of a love triangle.

Genre: Drama, Romance, Thriller, War

Actor: Brendan Fraser, Do Thi Hai Yen, Ferdinand Hoang, George Mangos, Holmes Osborne, Jeff Truman, Kevin Tran, Mathias Mlekuz, Michael Caine, Rade Serbedzija, Robert Stanton, Tzi Ma

Director: Phillip Noyce

Rating: R

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, 2006

After the 1975 release of the Maysles brothers’ Grey Gardens, Big and Little Edie Beale’s story captivated viewers and spawned a musical and a dramatized biopic about the reclusive, impoverished socialite mother-daughter duo. The Beales of Grey Gardens is a compilation of the remaining unreleased archival footage, released after the death of both subjects and David Maysles. For those unfamiliar with their story, the film might feel a bit random and contextless. But for Beale fans, and those familiar with their first documentary, this sticks close to the classic cinema vérité style of the Maysles, while also uncovering other sides of these interesting, eccentric former socialites, becoming a lovely tribute for them and their fans.

Genre: Documentary, Drama

Actor: Albert Maysles, David Maysles, Edith Bouvier Beale, Jerry Torre, Lois Wright

Director: Albert Maysles, David Maysles

Rating: NR

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, 1991

After a long life lived in a home one chose, it can be hard to uproot your entire life, especially in a country that seems diametrically opposed in manners and values. Before his American produced hits like Brokeback Mountain and Life of Pi, Ang Lee made his debut through Pushing Hands, a film entirely shot in America but produced from Taiwan, exploring from the Chinese perspective the generational conflict between Asian immigrants and the mainlander parents that they brought to have a good life. It’s humorous at certain moments, with the steady demeanor of Chu contrasted to everyone around him, but Pushing Hands stems from the understanding of someone who’s directly lived through it, unfolding into a thoughtful, sentimental drama that quickly established Lee’s directorial voice.

Genre: Comedy, Drama

Actor: Chit-Man Chan, Deb Snyder, Fanny De Luz, Haan Lee, Lung Sihung, Sihung Lung, Wang Bozhao, Wang Hung-Chang, Wang Lai

Director: Ang Lee

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, 1996

Films about drug dealing aren't particularly new, but the way Pusher delves into their lives feels different– more realistic than glamorous, somewhat like a guerrilla documentary, with the handheld camera as a silent, unnamed witness. As the camera follows low-level dealer Frank through the course of a week, Kim Bodnia skillfully garners empathy with the way he holds himself through the pressure, and does the opposite when he does the same wrongs that were done to him. The story itself may be simple, but writer-director Nicolas Winding Refn made his mark through this debut, inadvertently creating a franchise and influencing Danish cinema.

Genre: Action, Crime, Drama

Actor: Gordon Kennedy, Gyda Hansen, Jesper Lohmann, Karsten Schrøder, Kim Bodnia, Lars Bom, Laura Drasbæk, Levino Jensen, Lisbeth Rasmussen, Liv Corfixen, Mads Mikkelsen, Michael Hasselflug, Nicolas Winding Refn, Peter Andersson, Slavko Labović, Thomas Bo Larsen, Vanja Bajicic, Zlatko Burić

Director: Nicolas Winding Refn

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, 1991

Empirical truth is something that is observable, objective, and verifiable. However, without the ability to observe, one must find other means to obtain a set of observations– repeated, consistent answers to eventually parse out the reality. One must obtain proof. Proof is an Australian drama about a blind photographer named Martin, who uses his photos to get multiple viewpoints of what was present in that specific moment. Writer-director Jocelyn Moorhouse brilliantly uses that idea to craft a character that wields objectivity in order to protect himself and keep himself distant, as seen through the way he instantly trusts Andy due to his straightforward demeanor, and the way he attempts to drive away his housekeeper Celia to get her to see the worst of him, instead of the idealized, perhaps fetishized, image she creates of him. Proof challenges the photograph as a medium of truth, as well as the idea of complete honesty and trust in another person.

Genre: Drama, Romance

Actor: Belinda Davey, Cliff Ellen, Daniel Pollock, Frank Gallacher, Frankie J. Holden, Geneviève Picot, Heather Mitchell, Hugo Weaving, Jeffrey Walker, Russell Crowe, Saskia Post

Director: Jocelyn Moorhouse

Rating: R

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, 1989

When the wider culture doesn’t treat you the same way they treat the majority, it’s sometimes necessary to get mad, pivot, and assimilate to the majority’s ways in order to navigate the country and advocate for your rights. That’s the path Northern Cheyenne activist Buddy Red Bow took in Powwow Highway, one borne out of clear love of the community. But the beauty of this Native American story is the way Buddy learns to heal, to reconcile with his community’s folklore, and to recognize the resistance in serenely keeping what the wider majority tried to erase. Powwow Highway won’t be a perfect depiction of Native American culture, but it speaks true to the anger and heart the community still feels to this day.

Genre: Comedy, Drama

Actor: A Martinez, Amanda Wyss, Gary Farmer, Geoffrey Rivas, Graham Greene, Joanelle Romero, Rodney A. Grant, Sam Vlahos, Wes Studi

Director: Jonathan Wacks

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, 2012

The subject of the Catholic Pieta– the Virgin Mary cradling the corpse of Jesus– has captivated plenty of artists, most famously in the sculpture by Michelangelo in St. Peter’s Basilica. This time, however, director Kim Ki-duk twists the image into modern day Seoul, with a mourning mother and a loan shark in place of their more innocent inspirations. Though with more dialogue than his other works, Kim delves into this crime thriller with his signature slow burn, crafting an intense, emotional healing for the gruff, violent Lee Kang-do, while his past deeds come to catch up with him, and while he reckons with the way money has replaced all what makes life meaningful. While the (thankfully, pseudo-) incest may be hard to stomach, Pieta is nonetheless a haunting, compelling portrayal of revenge. Just don't watch this with your mom, though.

Genre: Drama

Actor: Cho Min-soo, Heo Joon-seok, Jin Yong-uk, Kang Eun-jin, Kim Jae-rok, Kwon Yul, Lee Jung-jin, Woo Ki-hong, Yoo Ha-bok

Director: Kim Ki-duk

Rating: NR

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, 2020

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

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, 2023

Nanpakal Nerathu Mayakkam might not immediately make sense to audiences new to director Lijo Jose Pellissery, but it’s still an interesting film that depicts Tamil culture. Also known as Like an Afternoon Dream, the contemplative bilingual film is centered around a prejudiced Malayali tour guide who wakes up as another man, specifically someone fluent in Tamil, and walks into the nearby village. Through vignettes focused on the village inhabitants, the film slowly unravels the dynamics between each of the villagers, flitting back to the tour bus on occasion to see how they’re faring. While some of the comedy goes over viewer’s heads, especially for people unfamiliar with the state, the slow-paced film feels like a fond memory from Pellissery. The film doesn’t explain anything at all, in the same way strange dreams refuse to do.

Genre: Comedy, Drama, Fantasy

Actor: 'Poo' Ram, Ashokan, Ashwanth Ashokkumar, G. M. Kumar, Mammootty, Namo Narayanan, Rajesh Sharma, Ramachandran Durairaj, Ramya Pandian, Ramya Suvi, Thennavan, Vipin Atley

Director: Lijo Jose Pellissery

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, 2023

Teen thrillers are fun, but there’s only so many times you can enjoy the warnings to not sneak out at night, to not give into peer pressure, and to not trust random strangers. NAGA is another teen night gone wrong, but unlike the regular suburban dangers, Sarah deals with, of all things, a vindictive camel out for blood, on top of teenage hijinks and other dangers women face in the conservative country of Saudi Arabia. While there are a tad too many events and some visuals might prove too dizzying for some viewers, NAGA is such a wild ride that’s so fun to follow.

Genre: Comedy, Drama, Horror, Thriller

Actor: Adwa Bader, Amal Alharbi, Jubran Al Jubran, Khalid Bin Shaddad, Yazeed Almajyul

Director: Meshal Aljaser

Rating: R

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, 1992

Of course, it won’t be surprising that Man Bites Dogs is particularly violent, given that the entire film is basically a documentary of a serial killer. But even those used to the gore, murders, and gruesomeness might be taken aback by Benoît (Poelvoorde)’s immediate murders, the matter-of-fact explanations of how he selects his targets, the casual conversations about random topics inbetween kills, and the easy way he lures the filmmakers (and the audience) to the amusement he gains from all of it. Man Bites Dog isn’t an easy watch, and it definitely deserved its controversial reputation, but we can’t deny how hard it is to look away.

Genre: Comedy, Crime

Actor: André Bonzel, Benoît Mariage, Benoît Poelvoorde, Édith Le Merdy, Jacqueline Poelvoorde-Pappaert, Jenny Drye, Malou Madou, Rémy Belvaux, Valérie Parent

Director: André Bonzel, Benoît Poelvoorde, Rémy Belvaux

Rating: NC-17

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, 2014

The people you love have different people, sometimes different worlds, in their lives that we don’t necessarily get to know about, though it depends on your loved ones. While most of the time, we would introduce the love of our lives to our families, sometimes, it’s not possible, especially if you’re not out to them yet. Hong Khaou's debut feature film is centered on that idea, and he handles this topic with the pace it needs, allowing Ben Whishaw and Cheng Pei-pei to carefully forge a gentle, genuine connection between two very different people bridged through Vann’s translations and their love for Kai.

Genre: Drama

Actor: Andrew Leung, Ben Whishaw, Cheng Pei-pei, Leila Wong, Morven Christie, Naomi Yang, Peter Bowles

Director: Hong Khaou

Rating: NR

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, 2021

Even if it doesn't provide the most comprehensive information about treatment and care for multiple sclerosis (MS)—especially for those who can't afford a ridiculously expensive stem cell transplant—this isn't really the point of Introducing, Selma Blair. This is still mostly a biographical documentary about a (self-confessed) "not-so-famous" celebrity, who gets to be incredibly honest about some of the privilege she enjoys, and how that privilege still doesn't make MS any easier. Blair's determination, her sense of humor, and her articulate way of expressing herself keep the film from descending into total sadness, but it also never shies away from the uglier, more difficult parts of her journey.

Genre: Documentary

Actor: Selma Blair

Director: Rachel Fleit

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, 1986

There is goodness within everyone… supposedly. However, there are some instances where the belief is almost foolish, some sins done against humanity that can't be explained, reasoned out, or defended. Henry: Portrait of a Serial Killer challenges that notion in three characters (the titular serial killer, his fellow ex-con Otis, and Otis’ sister Becky) and in the silent, unprotesting way writer-director John McNaughton makes us witness their lives. While true crime aficionados and horror fans might find this rather tame, the true horror of this portrait isn't in the kills, but rather in the way we’ve become accustomed to this violence, the same way a literal serial killer would be.

Genre: Crime, Horror, Thriller

Actor: Anne Bartoletti, Mary Demas, Michael Rooker, Tom Towles, Tracy Arnold

Director: John McNaughton

Rating: NR

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