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49 Best Challenging Movies to Watch

moodChallenging

Being challenged by a movie has to be one of the best experiences, period, not just of movie viewing. A harsh reality portrayed, or complex ideas being exposed, though-provoking problems and situations, or the film boosting a dark, interesting outlook on life – all are cherished and deeply humane interactions with this form of art and storytelling.

Below are recommendations handpicked by our staff from this mood featuring challenging movies.

Short Term 12 is exactly like being injured in a part of your body where you didn't think it was possible to get injured before. It will hurt but it will make you care. Natural and understated by budget and by purpose, it is powered by perfect performances that will take you on an emotional roller coaster ride you will never forget. It is at times sweet, at times depressing and at times hilarious. The thing is, without even taking into consideration its small budget or the importance of the issues it talks about - we would still consider Short Term 12 as one of the best movies of the past 20 years.

10
Best Film

Winner of an Oscar and a Golden Globe among endless accolades, A Separation is a movie about an Iranian couple faced with the decision of leaving the country for better opportunities or staying to take care of a sick parent. If you’ve ever been curious about the humans of Iran beyond the politics, and by cultural extension, humans of Middle-Eastern countries, watch A Separation. But hold it, “An interesting foreign movie” is not how A Separation should be viewed (it’s not Slumdog Millionaire). As someone who grew up in a middle-class Muslim family, this film may be the only one to thoroughly portray many integral aspects of my upbringing.  It perfectly depicts the delicate interaction between high moral standards and the realities of underdevelopment: how many bad people are only good people running out of options, and how parents raise their children in a shell of protection from the outside world while struggling to also introduce them to it. On a separate level, it also portrays how people live ready to have every privilege they have ever had revoked and how the constant need to “man up” transforms people, as well as the role of religion in all this. A Separation is my movie, and so I am asking you to watch this film the same way I’d want you to come visit and get to know my home country.

9.7
Best Film

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.

9.6
Best Film

In many ways, The Perks of Being a Wallflower is a modern masterpiece. It's a psychological experience - one that is sincere to its premise and the troubled nature of the human beings in it. You will be surprised by the depth of its many layers and the extents to which a similar movie can go (on paper it's a coming-of-age story). Its character-driven chemistry will catch you even more as it reaches its perfect mix between comedy, warmth, tragedy, and honest depiction of depression.

9.6
Best Film

A heart-breaking examination of a decaying shell of a once-bright marriage, this sad yet erotic-seeming story mixes happy flashbacks of attraction and desire with the grim reality of a dull life. It boosts an electrifying performance from Michelle Williams and Ryan Gosling, who seamlessly combine tenderness, rage, lust and sadness. This is a guaranteed tear-jerker, so make sure you've brought your Kleenexes!

9.5
Best Film

A dramatic take on the life and capture of Ted Kaczynski, popularly known as UNABOMBER(UNiversity and Airline BOMber) from the eyes of an FBI profiler. Kaczynski was responsible for 16 bombings, and it took 17 years for the FBI to catch him. To date, he's the target of the most expensive chase the FBI has ever launched. The show is not a mystery (facts are the matter of public domain) and doesn't even pretend to be one. Instead, it focuses on the complex motives of the UNABOMBER, as well as the bureaucracy that the FBI ran through trying to catch him. It's a really well-made, engrossing show that's hard not to watch in one take. It's 8 episodes of 40 minutes, so pick the time you start it wisely.

9.4

How far are you ready to go for a friend? You will find yourself puzzled with this question after you watch 4 Months, 3 Weeks and 2 Days. Set in Communist Romania, it's about a college student assisting her friend in arranging an illegal abortion. When things don't go as planned they find themselves in extremely tense and uncomfortable situations. Powerful performances and a realistic script drive a suspenseful and interesting experience. Won the Palme d'Or at Cannes.

9.2
Best Film

The Look of Silence is an incredible documentary from Director Joshua Oppenheimer, a follow-up/companion piece to his award-winning documentary The Act of Killing. Both films focus on the Indonesian Genocide of 1965-66, where the military government systematically purged up to one million communists. In this film an optician named Adi Rukun meets with various members of the death squad that murdered his brother, under the guise of providing them eye examinations. As he questions them about their participation in the killings, they show little remorse and in fact provide lurid details to the many executions. It’s a stunning and provocative look at the legacy of historical violence, along with the insidious propaganda that provoked it then and continues to justify it to younger generations.

9.1

A striking and revelatory documentary focused on the behaviour of captive Orcas and their treatment within SeaWorld and other theme parks around the world. At the center of the story is Tilikum, a bull Orca that has been responsible for the death of three individuals, and the legal and ethical challenges that have arisen from apparent cover-ups by officials. What happened to Tilikum to make him adopt such behavior? First-hand accounts by former whale trainers and experts deliver fascinating truths about Tilikum and the species as whole, with particular attention on their remarkable intelligence and advanced social behaviors. Blackfish will undoubtedly change your perspective on whale captivity indefinitely. It’s certainly not to be missed by anyone who appreciates top-notch documentary film-making as honest historical record.

9.0
Best Film

In the grand tradition of the ethnographic world tours like Mondo Cane, Samsara hits you in the face with the diversity and wonder of human life on earth. Unlike many of its predecessors, which often descended into colonialist gawping, Samara maintains a non judgmental gaze. This film uses no words or narration to travel the world showing you the breathtaking beauty of various countries, cultures, religions, cities, industries and nature. Shot on 70mm film, the definition and clarity has to be seen to be believed.

9.0
Best Film

One of those movies which are actually good for your education; think of it as a book you can read in two hours. It is, however, a very well-cast and well-filmed book. Hotel Rwanda is brutal and disturbing, which is only reasonable since it tells the story of one of the most horrific times in recent history. Led by an astonishing performance from Don Cheadle, it is overwhelmingly sad but an absolute must-watch.

9.0