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46 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

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

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

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

Directed by celebrated artist-turned-filmmaker Julian Schnabel, The Diving Bell and the Butterfly is the true story of French journalist and fashion editor Jean-Dominique Bauby (Mathieu Amalric), who suffered a devastating stroke at the age of 43. Almost completely paralyzed by what is termed “Locked-in Syndrome”, Bauby was left with only the operation of his left eye intact, leaving him forced to communicate via partner-assisted scanning (selection of each letter of the alphabet via blinking). Ultimately, Bauby employed this painstaking procedure to dictate his own memoir “Le Scaphandre et le Papillon”, which became a number one bestseller in Europe. The film alternates between Bauby’s interaction with his visitors and caretakers (including the dictation of his book) and his own dream-like fantasies and memories of his life prior to paralysis. With the title, Bauby uses the diving bell to represent his self-perceived state of isolation, akin to a deep-sea diver encased in an oxygenated chamber, and the corresponding butterfly to represent the freedom he enjoys as he often journeys quite magically through his own mind’s eye. It’s a somber yet engaging film full of heart and vision, featuring wonderful performances by the entire cast across the board.

9.0
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