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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). 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.

You may have heard about this 2019 critic-favorite from clips like this one of a kid running to flee the movie theater during a screening. “little billy ran the f**k out the door”, the caption reads.You will want to do the same. Recovering from losing her sister and her parents in a single incident, a young girl goes on a trip to Sweden to observe a ritual within a bizarre commune that occurs every 90 years. This cult’s idea of death and their traditions intersect with the girl’s grief to create unthinkable monstrosities.Note: while some readers praise the movie for its depiction of anxiety, I highly recommend against watching Midsommar if you suffer from panic attacks.

7.8

Such a good movie. The start is reminiscent of great, funny coming-of-age stories. However, a violent event quickly takes place and The Hate U Give becomes a powerful comment on police brutality in America, institutional oppression, and what it's like to be from a marginalized community but try to find your place in the world. But at the end, it's a 'movie' movie, directed by George Tillman Jr. who made the Barbershop movies and Men of Honor (with De Niro).

8.5
Best Film

Shot almost entirely in one take and on a tiny budget, and yet the central performance in this movie is still better than most big-budget dramas I’ve seen this year.Two indigenous women, one upper-class and the other impoverished, meet on the day that the rich one gets an IUD and the other one, pregnant, finds herself kicked out of her home. They spend a few hours together: they talk, they take cabs, walk, etc; and you as a viewer, follow them throughout their intimate yet difficult moments.If you like subtle movies that showcase how people live and interact with one another, beyond plot-obsessiveness, this is for you.

7.0

This documentary starts with Alex Lewis, who gets into a motorcycle accident and wakes up in the hospital not knowing who he is. He doesn’t remember anything (not even what a bicycle or a TV is, or who his mother or father are), but he remembers his twin brother, Marcus.When Alex gets back into his childhood home, he’s full of questions, and Marcus is full of answers. However, slowly, Marcus realizes his power to reshape Alex’s version of their past.Marcus leaves one important detail from Alex’s life that makes this documentary (as if it wasn’t already) such an insane story. I know I said it’s a sad movie, but it’s also fascinating and, ultimately, humanizing of the brothers’ experience.

8.2

Demian Bichir was nominated for an Oscar for his role in this movie where he plays an illegal immigrant and father. You might be wondering "who is that?", but trust me you won't after watching this movie. The kindness, complexity, and authenticity he brings to this story are unparalleled.A Better Life is about the illegal immigrant experience, about the line between the fear of being caught and the aspiration for a better future. It's an excellent and important movie.

7.6

This twisted movie is actually two movies, the credits even roll in between. The first half is gorgeous: talented dancers get together for a party and perform beautiful contemporary dance sequences. They introduce themselves through their audition tapes to join the dance group, but also through conversations at the party. The second half is less fun. It turns out someone had laced the sangria they've been drinking with a psychedelic drug. Not for the faint of heart or anyone who didn't like director Gaspar Noé's past movies (Enter the Void, I Stand Alone, etc).

7.1

Sometimes you can just tell a movie means way too much to the people who made it. That makes me want to watch it more than once, which is what I wanted to do with The Tale. But while I think it's such an amazing movie and everyone should watch it, I don't think I can stomach a second watch.. It is based on the director/writer Jennifer Fox's own story - recounting her first sexual experience at a very young age. It's about the stories we tell ourselves to deal with trauma, and in that sense, and with utmost honesty, it invites grief and closure for similar experiences. A powerful movie led by a powerful performance by Laura Dern as Jennifer.

8.1
Best Film

This is the type of movie I completely fell in love with but cannot articulate exactly why. Maybe it's the mixture of beauty and pain portrayed, maybe it's the intricate sounds and beautiful imagery, maybe it's the story, maybe it's all of the above. A woman is hit with sudden disability after an accident and calls on an unlikely companion, a night club bouncer by the name of Ali. Together they explore her new predicament and its implications, while forming a special bond. This is a movie that will call upon your internal strength, while portraying how us humans can become strong together. Most of all it provides an immensely powerful, ultimately simple story that is both touching and will stay with you for a very long time. Directed by Jacques Audiard (A Prophet).

8.1
Best Film

A delicate and profound exploration of loss, and an unbelievably well-made drama, Manchester By the Sea is a true triumph. Its focus on the characters, its timely unfolding of story elements, as well as its world class acting are only equal to the best European dramas. This deep and slow exploration of the human condition has rarely been successful in American cinema, if ever. The last best attempt was probably another movie  by director Kenneth Lonergan, You Can Count on Me. Manchester by the Sea is where he unveils his full potential, and takes the viewer deep into the tensions and history of a building handyman, Lee Chandler (Casey Affleck). His angry but quiet life is interrupted by news that his brother suffered a heart attack, and upon going back to his hometown he finds that he is the only one left to take care of his teenage nephew. A truly amazing movie, not to be missed, and a huge success too.  It grossed around $80 million on a budget of $8.5 million.

9.0

There is footage and coverage to prove that the pizza bomber story actually happened but watching Evil Genius: The True Story of America's Most Diabolical Bank Heist everything is so intriguing it is almost impossible to believe. A pizza-delivery guy shows up to rob a bank with what he says is a bomb secured around his neck, something that he claims is part of a treasure hunt. By robbing the bank, he will unlock the next set of clues that will allow him to defuse the bomb. Bank tellers comply but on the way out he is suddenly arrested by the police, who doubt his claims, handcuff him and keep him at a distance. The device he has around his neck then starts beeping. What follows is one of the most unusual investigations ever led by security forces, brilliantly framed by executive producers Duplass brothers. A perfect follow-up to their other amazing True-crime Netflix collaboration, Wild Wild Country, it’s a tight 4-episodes that is equally terrifying and intriguing.

8.5

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