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45 Best Challenging Movies to Watch

moodChallengingmovies

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

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

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