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43 Best Challenging Movies to Watch

Being challenged by a movie has to be one of the best experiences, period (not just of movie viewing). In this section, you will find recommendations that portray either: a harsh reality, complex or disturbing ideas, thought-provoking situations, or dark stories. Why watch them? Because in their portrayal of these things, they offer deeply human viewing experiences.

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
Very Best

This coming-of-age story based on the bestseller by the same name starts fun but veers towards darker territory. It's about a high-schooler who makes two older friends, played perfectly by Ezra Miller and Emma Watson. But as he gets closer to one of them, his anxieties and past trauma come to the surface. The impressive depth to which the makers of The Perks of Being a Wallflower were able to take it is what elevates it to greatness. It's the perfect mix between easy and challenging. If there is ever such a thing, it's this movie.

9.6
Very Best

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
Very Best

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
Very Best

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

It's often said that trying to make a comedy movie featuring a character with cancer is just a bad idea. And while there may be a good share of failed attempts in that category, 50/50 is not one of them. In a movie that comes closer to a believable real life situation than most, 50/50 manages to mine humor, pathos and simple honesty from a dark and traditional situation.  Starring Seth Rogan and Joseph Gordon-Levitt, this film isn't afraid to 'go there' but you'll enjoy the journey.

9.0
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