123 Best Challenging Movies to Watch

Staff & contributors

Find the best challenging movies to watch, from our mood category. Like everything on agoodmovietowatch, these challenging movies are highly-rated by both viewers and critics.

Understated in budget but lavished with praise, this semi-autobiographical drama by Daniel Destin Cretton flings its audience into the chaotic lives and personal crises of at-risk youths and the passionate social workers that aid them. In his first feature film, the young director draws the viewers into the storm of events and the emotional ups-and-downs of social work in America, going from uplifting to depressing and back – and every emotion in-between.

Set in the real-life and eponymous group home Short Term 12, devoted but troubled foster-care worker Grace is played by Brie Larson, whose shining performance in her first leading role was lauded by critics. Fans will also recognize the supporting actors Lakeith Stanfield and Rami Malek, who broke out in this movie. Short Term 12 is now considered one of the most important movies of 2013 – some say of the decade – owing to its immaculate writing, intimate camerawork, and gripping performances.

Not one but two Oscars as well as a Golden Globe are among this movie’s never-ending list of accolades. It was the first Iranian film ever to get an Oscar and the first non-English film ever nominated for Best Screenplay. Originally titled The Separation of Nader from Simin in Persian, it homes in on the dissolving relationship of a middle-class couple from Teheran – and the unintended consequences of tragic events.

However, this film is so intense, well-acted, and well-written, it defies categorization. To be sure, the movie does offer a painful look at a deteriorating marriage. It’s also timely, dealing with the politics of theocracy, economic underdevelopment, and social alienation. It presents tense moral dilemmas without pointing a finger. If you’re curious to learn about the humans of Iran and, by cultural extension, the humans of the Middle East beyond the scope of global politics, A Separation is also for you.

But please don’t call it world cinema, because this is no Slumdog Millionaire. Above all, it is a searing portrayal of human conflict, relationships, and morals. It is an almost perfect depiction of how many bad people are simply good people running out of options.

Aptly named ‘Rupert Grint on speed’ by one critic, Antoine-Olivier Pilon plays Steve, an abusive ADHD adolescent who just got out of a juvenile care facility for setting fire to the school cafeteria and injuring a fellow student. Similarly, his mother Diane, played by Anne Dorval, is a type of Lorelai Gilmore on speed – and to say that sparks fly when they clash is an understatement. But help comes from unexpected places: ‘Die’ makes friends with Kyla, an anxious teacher living across the street, who then gets sucked into this crazy, volcanic mess.

Mommy is the fifth feature film by French-Canadian don’t-call-him-a-hipster director Xavier Dolan and won the Cannes Jury Prize for its originality. It is shot in the 1:1 ‘portrait’ format, but every now and then a moment of exhilaration will crack open the frame. The brutality on screen is sugar-coated by an all-over-the-place soundtrack that includes the Counting Crows, Celine Dion, and Blue (Da Ba Dee) by Eiffel 65.

Shrill, violent, and demented, this out-of-control dark comedy will punch you in the guts. But it also aims straight for the heart and doesn't miss. Prepare to be continually torn between laughing out loud, clawing your seat, and covering your mouth in shock.

A wealthy paraplegic needs a new caretaker. His choice is surprising -- an ex-con down on his luck. Both of their lives are changed forever. Based on a true story, it is funny, touching, and very surprising.  It will have you rolling on the floor laughing one minute and reaching for your hankie the next. Intouchables is one of those perfect movies, that will easily and instantly make anyone's all-time top 10 list.

Legend has it that director Derek Cianfrance had the co-stars and co-executive producers Michelle Williams and Ryan Gosling live together in the same house for a month in preparation of their roles. The fictional couple they play in Blue Valentine lived in the same house. True or not, this created the harsh proximity, intensity, and claustrophobia that is a hallmark of this production. Blue Valentine brings us painfully close to the couple's attraction as well as their agony.

In this way, Blue Valentine is a heart-breaking examination of the decaying shell of a once-bright marriage. As sad as it is sexy, it mixes intense flashbacks of past desire with the grim reality of married life's monotony. It boasts an electrifying performance from Michelle Williams and Ryan Gosling, who seamlessly combine tenderness and lust, rage and sadness. This is a guaranteed tear-jerker, so make sure you've brought your Kleenexes!

Cure is about a mad society, where both cure and sickness might be one and the same. Director Kiyoshi Kurosawa subverts the police procedural into an interrogation without definite answers, an abstract study on the evil that resides and is suppressed in every person’s heart. Unlike most horror films, Cure’s scares are left in plain sight, hypnotically mesmerizing as they are gruesome, with a sense of mundanity associated with other Japanese masters like Ozu or Kore-eda. “At the time it just seemed the right thing to do,” a man answers when asked why he killed his wife, and it is this contradictorily calm, nonchalant demeanor that creates a feeling of unease in the film’s horror aesthetic.

How far would you go to help a friend? The answer to this question might turn out quite differently after you have lived through the 2-hour squalor of 4 Months, 3 Weeks and 2 Days. Set in the bleak late-1980s reality of Communist Romania, under the ironclad rule of Stalinist dictator Nicolae Ceaușescu, Anamaria Marinca and Laura Vasilu play Otilia and Gabriela, two small-town students. Otilia volunteers to help Gabriela go through with an illegal abortion, which takes place in a shoddy hotel room with the help of a man named Bebe (played by Vlad Ivanov). When things don't go as planned, they find their situations quickly going from very bad to outright horrible. Powerful performances, a realistic script, and director Cristian Mungiu's technical finesse create an experience that will force you to relive the desperation the two women must endure. Little wonder that it won the Palme d'Or at Cannes in 2007.
A follow-up/companion piece to the award-winning The Act of Killing, The Look of Silence is another compelling documentary from Director Joshua Oppenheimer. Both films aim attention at the Indonesian Genocide of 1965-66, when the military government systematically purged up to one million communists. While the first film's focus was on the culprits and on providing facts, the second one lets us meet the victims. One victim in particular: a soft-spoken optician named Adi Rukun, who meets with various members of the death squad who murdered his elder brother Ramli, under the guise of giving them an eye test. As he questions them about the killings, the murderers, again, show little remorse and eagerly provide the lurid details to the many executions. It's a stunning and provocative look at the legacy of historical mass killings, along with the insidious propaganda that provokes them, and continues to justify them to younger generations. A testament to the power of cinema to remember the forgotten.

Ahmed plays Ruben Stone, a heavy metal drummer, who plays in a band and lives in a tour bus with his girlfriend Lou (Olivia Cooke). Quickly after meeting the couple, we witness the touring musician drastically losing his hearing. As recovering addicts with little financial means, they soon run out of options. Lou desperately wants to prevent Ruben's relapse into addiction and so she helps him retreat to a deaf community group home, run by the illustrious Joe, a truly amazing character played by the equally amazing Paul Raci, himself the hearing son of deaf parents. There is something deeper going on though: the question of what disability is, and how, despite how it drastically changes Ruben's life, it might not be his biggest problem. In addition to the stellar acting and delicate writing, we experience his condition through the incredible sound design used by director Darius Marder, complete with muffled conversations, garbled noises, and piercing silence. This is a movie to be taken in completely. Above all, it's about Riz Ahmed's performance. He learned to play drums, sign language, and studied deafness ahead of the shooting, and he does not strike a wrong note.

Directed by celebrated artist-turned-filmmaker Julian Schnabel, who won an award in Cannes for it, The Diving Bell and the Butterfly is the true story of the Parisian journalist and fashion editor Jean-Dominique Bauby (Mathieu Amalric), who suffered a devastating stroke at the age of 43. Paralyzed almost completely by what is termed locked-in syndrome, his left eye was the only part of his body that he was still able to move. In a Herculean effort, Bauby learned to blink in an alphabet code that eventually enabled him to communicate. The film alternates between Bauby's interaction with his visitors and caretakers (including painstakingly dictating his memoir, the titular Le Scaphandre et le Papillon) and dream-like fantasies and memories of his life prior to paralysis. The title alludes to this juxtaposition: the diving bell representing his final state of isolation, akin to a deep-sea diver under a bell, and the butterfly as a symbol for his blinking eye and the freedom he has in his mind, dreams, and imagination. Shot from Bauby's perspective, we see what he sees. Be it his divorced but loyal wife and his family visiting him, or his old father, played by Max von Sydow, which is probably the scene in this fascinating movie that will make you lose it and weep like the rest of us.

In Lumon, a company that resembles the increasingly intrusive oligarchs of Big Tech, Mark (Adam Scott) and his colleagues undergo a procedure that allows them to separate their work memories from their non-work memories. It sounds like a dream: the perfect work-life balance. But things get complicated when one colleague mysteriously leaves and is replaced by confused new hire, Helly (Britt Lower). Mark and Helly dig into shocking truths about what they really do, and for whom.

Just like the endless halls of Lumon, Severance is filled with twists and turns, many of which are impossible to see coming. Slow, smart, and sneaked with a dystopian eerieness that doesn’t feel all that far off, Severance is sure to leave you wary of corporate slavishness, if you aren’t already. 

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!

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. 

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.
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.