473 Best Challenging Movies to Watch (Page 23)

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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331. Proof, 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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332. Powwow Highway, 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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333. Pieta, 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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334. Never Rarely Sometimes Always, 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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335. Naga, 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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336. Man Bites Dog, 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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337. Malbatt: Misi Bakara, 2023

After Black Hawk Down (2001), the casual moviegoer would have thought that the rescue operation was only conducted by American soldiers. In reality, it was a multinational effort, and Malaysia’s side of the story has finally been depicted in MALBATT: Misi Bakara. Surprisingly, it doesn’t play out as a straightforward, action-packed rescue mission– writer-director Adrian Teh does deliver the action, but the film also contemplates about the team itself: how they made sense of their opposition towards a country they shared religions with, and how they experienced the ignorance from American soldiers that didn’t even know where Malaysia was. While some introductory sequences falter, and the film fumbles certain green screen moments, MALBATT: Misi Bakara brings both the spectacle and the drama that makes it stand out from other depictions of the rescue mission.

Genre: Action, Drama, History, War

Actor: Adlin Aman Ramlie, Adrian Teh, Bront Palarae, Dini Schatzmann, Fauzi Nawawi, Gambit Saifullah, Hairul Azreen, Iedil Putra, Musa Aden, Nafiez Zaidi, Paul Biddiss, Safwan Nazri, Shaheizy Sam, Shiqin Kamal, Syazwan Zulkifly, Taufiq Hanafi, Theebaan Govindasamy, Tony Eusoff, Virgile Mangiavillano, Yuna Rahim, Zahiril Adzim

Director: Adrian Teh

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338. Lilting, 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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339. Introducing, Selma Blair, 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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340. Henry: Portrait of a Serial Killer, 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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341. De Humani Corporis Fabrica, 2023

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

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342. Every Body, 2023

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

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343. Eldorado: Everything the Nazis Hate (2023)

Factually accurate yet still earnest in its mission, Eldorado: Everything the Nazis Hate delivers what it promises. While the title comes from the club's name, the film is less about the club and more about the LGBTQ+ experience in Nazi Germany. To do this, the documentary focuses on Eldorado's individual patrons. Directors Benjamin Cantu and Matt Lambert interweave their stories with historical context. For example, patrons like trans pioneers Charlotte Charlaque and Toni Ebel shed light on historical advancements for the LGBTQ+ community. While it can be overwhelming when Eldorado introduces its patrons and their lovers and their political rivals, the film stays focused on what it sets out to do. Eldorado remains an important reminder of the LGBTQ lives lost and the love that still remains.

Genre: Documentary

Director: Benjamin Cantu

Rating: R

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344. Dirk Gently’s Holistic Detective Agency, 2017

Dirk Gently is not an easy watch. Right from the get-go, it comes bursting with wild mysteries, supernatural elements, cartoonish developments, and very loose ends. But there's something to be said about its inexplicability. It doesn't dumb things down or mold itself into anything recognizable, and that ambitious feat alone makes it a standout in a sea of TV replicas. It is its own weird thing, and it's hard not to like that about the show.

The characters seem random at first, but they will disarm you with their unexpected humanity. The titular Dirk Gently, for instance, initially comes off as a Doctor Who-like know-it-all, but underneath his chirpy facade is a hurt man who longs for connection. Inversely, his accomplice Todd Brotzman may seem like a typical nice guy, but his darker nature reveals itself incrementally and rather smartly.

This is a show that requires you to trust the process, to believe in "holism" as they say (aka the interconnectedness of everything, even the most seemingly random thing), and the sooner you submit to that belief, the easier and ultimately enjoyable the show gets.

Genre: Comedy, Crime, Sci-Fi & Fantasy, Science Fiction

Actor: Aaron Douglas, Agam Darshi, Ajay Friese, Alan Tudyk, Amanda Walsh, Christopher Russell, Dustin Milligan, Dylan Schombing, Elijah Wood, Fiona Dourif, Hannah Marks, Hunter Dillon, Izzie Steele, Jade Eshete, John Hannah, Lee Majdoub, Michael Eklund, Miguel Sandoval, Mpho Koaho, Neil Brown Jr., Osric Chau, Richard Schiff, Roger Cross, Samuel Barnett, Tony Amendola, Tyler Labine, Viv Leacock

Rating: TV-14

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345. Career Girls, 1997

	
Growing up and growing old over time leads to natural separation between friends, but it doesn’t mean that you’ll never see each other again. Career Girls depicts an ordinary reunion between two women Hannah and Annie, but through the subtleties of writer-director Mike Leigh’s dialogue, and the chemistry between Katrin Cartlidge and Lynda Steadman, it captures the weathered yet fond friendship they share, despite all that has happened to them. It’s naturally bittersweet, the same way we remember old friends, but it's also comforting, just having a friend that sees you for who you are, regardless of the time that has passed since you’ve last met.Genre: Drama
Actor: Andy Serkis, Joe Tucker, Kate Byers, Katrin Cartlidge, Lynda Steadman, Margo Stanley, Mark Benton
Director: Mike Leigh

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