306 Best Challenging Movies to Watch (Page 2)

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.

The Sanskrit word Samsara refers to the wheel of life and roughly translates to “continuous flow”. And, indeed, Samsara takes us on an entrancing journey, chronicling the never-ending cycle of birth, life, death, and re-birth that life, big and small, goes through—at least according to the religions that were born on the Indian continent. Shot on 70mm film and utilizing computerized camera movements as well as time-lapse photography, this film by American director Ron Fricke delivers absolutely breath-taking visuals. Whether it's awe-inspiring vastness or the close-up of a human face, its narration-less narrative integrates every aspect of human and natural life regardless of scale or location. The scope of this effort is truly awe-inspiring and the clarity of it has to be seen to be believed. An unusual and magical film!

Genre: Documentary

Actor: Balinese Tari Legong Dancers, Hiroshi Ishiguro, Ni Made Megahadi Pratiwi, Olivier De Sagazan, Puti Sri Candra Dewi, Putu Dinda Pratika

Director: Ron Fricke

Rating: PG-13

Nothing about Saint Omer is easy. A female Senegalese migrant (Guslagie Malanga) is put to trial for committing infanticide, but throughout the film, it becomes clear how much of a victim she is too, of an uncaring and deeply prejudiced society. “What drove her to madness?” Her attorney asks at one point. We’re not sure. We're not necessarily asked to side with her, nor answer the many hard-hitting questions brought up in the film, but we sit with the uneasiness of it all and, in that silence, confront our ideas about motherhood, womanhood, personhood. 

This confusion is what makes the film so compelling. Despite the court’s best efforts, Laurence isn’t meant to be understood. She’s meant to be an example of the ever-ambiguous, forever-complicated, always-hurt person. It’s human nature after all to be this complex and messed up. The film shows us that the best that we can do in situations like this is to listen, understand, and as our protagonist Rama (Kayije Kagame) does, make peace with the noise. 

Genre: Crime, Drama

Actor: Aurelia Petit, Guslagie Malanda, Kayije Kagame, Louise Lemoine Torrès, Salimata Kamate, Valérie Dréville, Xavier Maly

Director: Alice Diop

In a world where mortality has been overcome, people watch in awe as the as the 118-year-old Nemo Nobody, the last mortal on Earth, nears his end. He is interviewed about his life, recounting it at three points in time: as a 9-year-old after his parents divorced, when he first fell in love at 15, and as an adult at 34. The three stories seemingly contradict each other. Utilizing non-linear cinematography, Belgian director Jaco Van Dormael presents each of these branching pathways as a version of what could have been. The result is a complex, entangled narrative. That and the movie's ensemble cast, featuring Jared Leto, Sarah Polley, and Diane Kruger, have turned Mr. Nobody into a cult classic. The soundtrack, featuring several of the beautifully restrained music by Eric Satie, is also considered a masterpiece. While it is surely not for everybody, this is trippy, intimate, and existential sci-fi at its best.

Genre: Drama, Fantasy, Mystery, Romance, Science Fiction

Actor: Aaron Landt, Alice van Dormael, Allan Corduner, Andrew Simms, Audrey Giacomini, Ben Mansfield, Carlo Mestroni, Catherine Demaiffe, Christelle Cornil, Christophe Beaucarne, Clare Stone, Daniel Brochu, Daniel Mays, David Kennedy, David Schaal, Diane Kruger, Dominique Warnier, Harold Manning, Harry Cleven, Hugo Harold-Harrison, Jan Hammenecker, Jared Leto, Jenna Wheeler-Hughes, John Churchill, Juliette Van Dormael, Juno Temple, Laura Brumagne, Laurent Capelluto, Leni Parker, Linh Dan Pham, Lola Pauwels, Manfred Andrae, Marc Zinga, Marie-Ève Beauregard, Martin Swabey, Natasha Little, Nicholas Beveney, Olivier Bony, Pascal Duquenne, Philippe Godeau, Philippe Lévy, Pierre Chaves, Rhys Ifans, Roline Skehan, Sandrine Laroche, Sarah Gravel, Sarah Polley, Serge Larivière, Stéphane Taillasson, Sylvie Olivé, Tedd Dillon, Thomas Byrne, Toby Regbo, Vincent Dupont, Virginie Bordes, Vito DeFilippo

Director: Jaco Van Dormael

Rating: R

Winning him Best Director at the Academy Awards, Kenneth Lonergan's drama Manchester By the Sea is a delicate and profound study of loss and grief—and a true triumph. Its focus on characters, well-paced unfolding as well as world-class acting are only equal to the very best of European dramas. This type of quiet exploration of the possibility that grief cannot be overcome has rarely been successful in American cinema, if ever. The last best attempt was probably You Can Count on Me. Originally a playwright, this is Lonergan's third film and Manchester by the Sea is where he unveils his full potential. It follows a depressed handyman, Lee Chandler (Casey Affleck), who leads a quiet but angry life. After his brother dies, he returns to his hometown only to discover that he is the only left to take care of his teenage nephew. There, he is confronted with his past and the blue-collar community from which he was raised. Co-produced by Matt Damon, it grossed around $80 million on a budget of $8.5 million. One of the most noted films of 2016.

Genre: Drama

Actor: Allyn Burrows, Anna Baryshnikov, Anthony Estrella, Ben Hanson, Ben O'Brien, Brian A. White, C.J. Wilson, Carolyn Pickman, Casey Affleck, Christian J. Mallen, Danae Nason, Ellie Teves, Erica McDermott, Frank Garvin, Gretchen Mol, Heather Burns, Ivy O'Brien, Jackson Damon, Jami Tennille, Joe Stapleton, Josh Hamilton, Kara Hayward, Kenneth Lonergan, Kt Baldassaro, Kyle Chandler, Lewis D. Wheeler, Liam McNeill, Lucas Hedges, Matthew Broderick, Michelle Williams, Missy Yager, Nellie Lonergan, Oscar Wahlberg, Quincy Tyler Bernstine, Richard Donelly, Robert Sella, Ruibo Qian, Shawn Fitzgibbon, Stephen Henderson, Stephen McKinley Henderson, Susan Pourfar, Tate Donovan, Tom Kemp, Wendy Overly, William Bornkessel, Zain Ullah

Director: Kenneth Lonergan

Rating: R

, 2017

Named after a slur for people of Asian descent, this 2017 film put Justin Chon on the map as a director. More than that, he also starred as the main lead in this raw and uncompromising period drama about Asian-Americans and the LA riots in 1992. Shot completely in black and white, it tells the story of Eli, a scrawny Korean-American, who runs his family shoe store with his brother, Daniel (David So), in several vignettes. They strike up an unlikely friendship with Kamilla (Simone Baker), a black kid from around the way, whose family is not happy with her hanging out with the two brothers. Amidst the ubiquitous violence in LA at the time, the Rodney King riots as well as a tragic shooting of a black teenager by a Korean convenience store owner, it shines the light on America's intra-minority race relations and the more unseen stories behind them. A topic that has come back to haunt America in the 2020s. The film is fierce as it is funny, harsh as it is playful. Uplifting and unsettling.

Genre: Drama

Actor: Ben Munoz, Curtiss Cook Jr., David So, Isaiah Jarel, Justin Chon, Natalie Sutherland, Omono Okojie, Sang Chon, Simone Baker

Director: Justin Chon

Rating: Unrated

A very poetic film by Tony Kaye (American History X) about an English Literature teacher (Adrien Brody - "The Pianist") who only works as a substitute in schools which are located in very poor urban areas. The reason behind his choice is that he doesn't want to bond too much with his students and colleagues because he is trying to control his dark emotions about life and the triviality of our existences (although it sounds depressing it is absolutely not). He also takes care of his last family connection, his grandfather, to whom he is very close and who lives in an elderly home. Unsurprisingly, their relationship is very emotional and deep. Every time you think about your existence, your place in the world, your interactions with other people; watch Detachment.

Genre: Drama

Actor: Adrien Brody, Betty Kaye, Blythe Danner, Bryan Cranston, Celia Au, Chris Papavasiliou, Christina Hendricks, Isiah Whitlock Jr., James Caan, Josh Pais, Louis Zorich, Lucy Liu, Marcia Gay Harden, Mary Joy, Patricia Rae, Ralph Rodriguez, Reagan Leonard, Ronen Rubinstein, Samantha Logan, Sami Gaye, Sami Gayle, Tim Blake Nelson, William Petersen

Director: Tony Kaye

Rating: Not Rated

In 2009, Departures surprised everybody by winning the Academy Award for Best Foreign Language Film, instead of everyone's favourite, Ari Folman's Waltz of Bashir. This is even more surprising since this Japanese comedy almost never saw the light of day because many distributors refused to release it at first for its humorous treatment of a very human, but weirdly taboo subject: what happens when you die. Daigo Kobayashi (played by former boyband member Masahiro Motoki) just bought an expensive cello when he learns that his Tokyo-based symphony orchestra is going bankrupt. Daigo and his wife Mika, played by Ryôko Hirosue, decide to move back to his hometown, where he applies for an opening at what he thinks is a travel agency, hence the departures. You might have guessed by now that what he was applying for was, in fact, the job of an undertaker—a profession considered unclean in Japan. It's one of those rare movies that will make you laugh, to making you cry, and laugh again. It's dead-on!

Genre: Drama

Actor: Justin Lukach, Kazuko Yoshiyuki, Kimiko Yo, Maisie Williams, Masahiro Motoki, Nina Dobrev, Ryoko Hirosue, Ryosuke Otani, Sanae Miyata, Scott Wilson, Takashi Sasano, Taro Ishida, Tatsuo Yamada, Tetta Sugimoto, Tōru Minegishi, Tsutomu Yamazaki, Tyler Hoechlin, Yukari Tachibana

Director: Yōjirō Takita

Rating: PG-13

If you liked Netflix’ Stranger Things gloomy suspense, sit tight because there is a lot more of where that came from in Dark. Here is what they have in common: the aesthetic, great music, and they’re both about the disappearance of a child. Other than that, it is very difficult to compare Dark to anything else I’ve seen before.

This German show is about a town with a long and dark history, which is brought to the forefront of the collective conscious when a child goes missing. The plot twists and turns through decades of history – and that’s as much as I will share without ruining the show for you. 

Dark uses beautiful aesthetic, both visually and musically, to be compelling and painfully tension-ridden. 

Season two has more bouncing between timelines and more dark and inexplicable events, as now six people are missing. 

Genre: Crime, Drama, Mystery, Sci-Fi & Fantasy, Science Fiction

Actor: Anatole Taubman, Andreas Pietschmann, Angela Winkler, Anne Ratte-Polle, Jördis Triebel, Karoline Eichhorn, Lisa Vicari, Louis Hofmann, Maja Schone, Mark Waschke, Michael Mendl, Oliver Masucci, Sebastian Rudolph, Stephan Kampwirth

Rating: Not Rated, TV-MA

Orcas killing people? Saving whales? There was indeed a time when these issues were frontpage news and that might be the reason why this sounds like a 90s cliché to you. You might agree that this issue should be staunchly dealt with once you've watched Gabriela Cowperthwaite's 2013 documentary. Orcas still being held captive by marine parks like SeaWorld to perform stunts and to parade around swimming pools to entertain ticket-buying families. Blackfish is the story of one of them in particular: a bull Orca named Tilikum, who has killed several people as a result of their immoral imprisonment. Similar incidents tend to be covered up by the parks' operators and management. They are, however, attributable to the fact that the animals are quiet simply driven mad by the unnatural conditions they are subjected to. They are not born as killers, they are turned into them. First-hand accounts by former whale trainers and experts deliver fascinating truths about Tilikum and the species as whole, elaborating on their remarkable intelligence and social behaviors. For those unaware of this, this passionate documentary makes for a chilling watch.

Genre: Documentary, Drama

Actor: Anderson Cooper, Carol Ray, Dean Gomersall, Gabriela Cowperthwaite, James Earl Jones, John Hargrove, John Jett, John Sillick, Mark Simmons, Mercedes Martinez, Samantha Berg, Tamarie Tollison, Tilikum, Whoopi Goldberg

Director: Gabriela Cowperthwaite

Rating: PG-13

, 2011

It might seem like a no-brainer that trying to make a comedy movie featuring a character with cancer is not a great idea. And while there may be a good share of failed attempts in that category, 50/50 is not one of them. And then it might come as a surprise that this subtle attempt at cancer comedy comes courtesy of Superbad creators Seth Rogen and Evan Goldberg. It also stars indie cutie Joseph Gordon-Levitt as the young and fit Adam Lerner, who works as a writer for public radio before learning that he has malignant tumors all along his spine. Between his overbearing mum (Anjelica Huston), slightly obnoxious but good-hearted bestie (Seth Rogen), self-help groups, and his therapist (played by Anna Kendrick), he struggles to find a way of acquiescing to his 50/50 chance of survival. Similarly, 50/50 strikes a delicate balance between the bromance gags, the date-movie elements, and the grave subject matter at its heart. It manages to mine humor, pathos, and simple honesty from a dark situation, and is not afraid to “go there”. The result is truly compassionate comedy.

Genre: Comedy, Drama

Actor: Adrian Glynn McMorran, Amitai Marmorstein, Andrea Brooks, Andrew Airlie, Anjelica Huston, Anna Kendrick, Beatrice King, Brent Sheppard, Bryce Dallas Howard, Cameron K. Smith, Chilton Crane, Christopher De-Schuster, D.C. Douglas, Daniel Bacon, Donna Yamamoto, Jason Vaisvila, Jessica Parker Kennedy, Jonathan Levine, Joseph Gordon-Levitt, Laura Bertram, Lauren Miller, Luisa D'Oliveira, Marie Avgeropoulos, Matt Frewer, Matty Finochio, P. Lynn Johnson, Peter Kelamis, Philip Baker Hall, Sarah Smyth, Serge Houde, Seth Rogen, Stephanie Belding, Stephen Colbert, Sugar Lyn Beard, Tom MacNeill, Veena Sood, Will Reiser, William 'Big Sleeps' Stewart, Yee Jee Tso

Director: Jonathan Levine

Rating: R

Directed and co-written by Craig Johnson (who made The Adolescents with Mark Duplass), The Skeleton Twins is a beautiful piece of drama, dealing with some dark themes. It does so with surprising success, given that the two main actors are seasoned comedians with little to no experience in the genre. And yet, it is precisely the two leads that turn this bleak comedy-drama into a somber, haunting, but beautiful watch. Bill Hader is amazing as the depressed and suicidal gay man, Milo, who is reunited with his estranged twin Maggie (Kristen Wiig) after a series of unfortunate events. Their attempts at repairing their fractured relationship also forces them to confront the trajectory of their own lives, while they rediscover their erstwhile childhood friendship and long-lost camaraderie. Again, don't expect a traditional comedy, but an honest display of the complexities of sibling relationships, mental health, and how conflict, compassion, and understanding fit into it all.

Genre: Drama

Actor: Adriane Lenox, Bill Hader, Boyd Holbrook, Cliff Moylan, David Garelik, Eddie Schweighardt, Genevieve Adams, Ian Hyland, Jennifer Lafleur, Joanna Gleason, Kathleen Rose Perkins, Kristen Wiig, Luke Wilson, Paul Castro Jr., Sydney Lucas, Truck Hudson, Ty Burrell

Director: Craig Johnson

Rating: R

Difficult but essential viewing, Procession tracks the progress of six men undergoing art therapy—specifically, by creating short filmed scenes to process their trauma from being sexually abused by Catholic priests. The resulting films we get to see are wildly varied in the emotions they express, forming a rich and powerful tapestry of the effects abuse can leave on individuals. And to see these men confront the worst events of their lives through filmmaking begins to feel like validation for filmmaking itself, that it can truly be an art form that changes and saves lives. But even more striking, somehow, is the unbreakable bond that forms among these survivors throughout this entire process, captured with reverence and overflowing compassion by director Robert Greene.

Genre: Documentary

Actor: Dan Laurine

Director: Robert Greene

The best thing about The Rehearsal—Nathan Fielder's elaborate Russian doll of social experiments and self-examination—is how seamlessly it goes from prank comedy to surrealist horror. The show's concept of staging situations where real people can practice making an important decision (complete with actors playing all the background characters) pays off in spades. Fielder's insistence on over-preparation collides beautifully with the unpredictability of human behavior, leading to some of the funniest and weirdest interactions to grace TV.

But the greatest trick that The Rehearsal has up its sleeve is Fielder, playing a version of himself using this show to understand how to live a meaningful life. As he stretches these rehearsals beyond their limit (at certain points, recreating his own rehearsals with someone playing himself), his character's persona also begins to crack. Suddenly the series isn't just a comedy, but a poignant reflection on empathy and forgiveness, and a psychological mind-bender about an egomaniac who refuses to give up control of reality itself. There's nothing else like it on television.

Genre: Comedy, Documentary

Actor: Nathan Fielder

Director: Nathan Fielder

Poetry is a masterpiece from one of South Korea's most cherished movie directors, Lee Chang-dong. The simple story follows the everyday life of a grandmother, Mija, who works as a caretaker for a living. To fill her inner emptiness, she decides to join a poetry club with other grandmothers in her neighborhood. Meanwhile, as Mija deals with her own financial and health problems, she struggles to connect with her teenage grandson — only to find out that he is keeping a dark secret. If you are familiar with Lee Chang-dong works, then you know that the movie will tug at your heartstrings. But if you aren't, prepare to be moved.

Genre: Drama

Actor: Ahn Nae-sang, Chang Hyae-jin, Eun-yeong Kim, Hee-ra Kim, Jang Hye-jin, Jeong-hie Yun, Kim Eun-yeong, Kim Hee-ra, Kim Ja-young, Kim Jong-goo, Kwon Hyuk-soo, Lee Da-wit, Min Bok-gi, Park Hyun-woo, Park Myung-shin, Yoon Jeong-hee

Director: Chang-dong Lee, Lee Chang-dong

Rating: TV-PG