448 Best Challenging Movies to Watch (Page 28)

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One of the cinema’s most noble roles is to challenge pre-conceived perceptions and tackle difficult questions about humanity and the world. Here are some of the most important and topically challenging movies to stream right now.

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, 2013

Sometimes it's hard to relate to foreign movies because of the different cultures, languages and actors. But Miracle in Cell No. 7 transcended the language barriers for me and delivered one of the most touching stories I have ever seen. It's a Korean film about the intricate yet simple love story between a mentally challenged father and his daughter. When the father is wrongly accused of a crime he did not commit and is sent to prison, his personable character eventually causes the prisoners around him to help reunite him with his daughter in prison. Warning: many tissues will be needed.

Genre: Comedy, Drama, Family

Actor: Choi Ro-woon, Dal-su Oh, Gal So-won, Han Yi-jin, Im Jae-min, Jeong Man-sik, Jin-young Jung, Jo Deok-hyeon, Jo Jae-yoon, Jo Jae-yun, Jung Han-bi, Jung Hee-tae, Jung Jin-young, Jung Man-sik, Jung-tae Kim, Kal So-won, Kang Seung-wan, Kang Ye-seo, Kim Jung-tae, Kim Ki-cheon, Kim Ki-chun, Kim Se-dong, Kyul Hwi, Lee Seung-yeon, Lee Yoon-hee, Man-shik Jeong, Man-sik Jeong, No Kang-min, Oh Chang-kyung, Oh Dal-su, Park Gil-su, Park Kil-soo, Park Sang-myeon, Park Shin-hye, Park Won-sang, Ryu Seung-ryong, Seung-ryong Ryu, Shin-Hye Park, So Won Kal, Song Lee-woo, Won-sang Park, Yeo Moo-yeong, Yoon Sun-Woo

Director: Hwan-kyung Lee, Lee Hwan-kyung

Rating: N/A, Not Rated

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, 2023

While gay acceptance has been improving in most of the world, unfortunately, this acceptance isn’t universal to all sexualities and queer gender identities, especially for people of color. Femme depicts this difference through the relationship of Jules, a black gay drag queen, and Preston, a white masculine closeted gay drug dealer. As Jules deepens their relationship for revenge, and Preston opens up and allows himself to become more vulnerable, the film explores the way toxic masculinity and violence still dictates most of their dynamic, through an unsettling, sexually charged, stylish approach from the debut co-writers and directors Sam H. Freeman and Ng Choon Ping. However, Femme is particularly uneven, more focused on humanizing the aggressor rather than prioritizing the survivor.

Genre: Drama, Thriller

Actor: Aaron Heffernan, Antonia Clarke, Asha Reid, George MacKay, John McCrea, Luis Torrecilla, Moe Bar-El, Nathan Stewart-Jarrett, Nima Taleghani, Peter McPherson

Director: Ng Choon Ping, Sam H. Freeman

Rating: NR

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, 2012

Electrick Children is the debut film for director Rebecca Thomas and one of the most unique and visually stunning films I’ve seen in a while. This gem is about a teenager born and raised in a religious community who believes she has been impregnated with the son of God from a cassette tape she listened to. She decides to run away to neighboring Las Vegas in search of the real father, “the man who sings on the cassette tape.” Heavy stuff, man. Electrick Children is one of those films you see once and it stays with you. It deals with teenagers so delicately and accurately, depicting the butterflies, the excitement, the romance, the heartbreak, the trials and tribulations of this age and beyond. Its cinematography is hypnotizing and its soundtrack is divine (listen to Top of the Hill by Conduits on repeat and it’ll start to have an impact on your life.) Its plot is completely fresh and is able to grab and keep your attention from the first second until the very end. Watching this film made me want to go back in time and fall in love all over again. It made me feel lusty and gave me butterflies and made my heart flutter unlike any other film I’ve seen. You can’t pass this one up.

Genre: Drama

Actor: Bill Sage, Billy Zane, Cassidy Gard, Cynthia Watros, John Patrick Amedori, Julia Garner, Liam Aiken, Rachel Pirard, Rory Culkin

Director: Rebecca Thomas

Rating: R

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, 1997

With a great cast, a relevant story, and a stirring romance, The Boxer is all set to be a great film, but the resulting feature feels like a letdown. Irish director Jim Sheridan has teamed up with English actor Daniel Day Lewis for a feature depicting the Troubles in Northern Ireland, and for the most part, it’s decently made, but the film struggles to balance the romance and the politics of its story, with Day Lewis’ boxing lagging behind. There are plenty of interesting threads here– the right to self-determination, on both the individual and national level, the loss of youth, and the way war makes cities turn on themselves– which are all emotionally carried by the performances, but the structure fails to organize these ideas into a daring and cohesive statement. The Boxer isn’t a terrible watch, but it just feels like it could have delved more deeply into the conflict, or better yet, could have been at least two separate movies.

Genre: Drama, Romance

Actor: Brian Cox, Brian Milligan, Britta Smith, Ciarán Fitzgerald, Daniel Day-Lewis, David Hayman, Des Braiden, Don Foley, Eleanor Methven, Emily Watson, Frances Tomelty, Gavin Kennedy, Gerard McSorley, Ian McElhinney, Jer O'Leary, Joan Sheehy, John Cowley, John Wall, Ken Stott, Kenneth Cranham, Liam Carney, Lorraine Pilkington, Maria McDermottroe, Mark Mulholland, Mick Tohill, Niall Shanahan, Nye Heron, Paul Ronan, Peter Sheridan, Tom Bell, Tom Maguire, Veronica Duffy, Vinny Murphy

Director: Jim Sheridan

Rating: R

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, 2023

While morbidly titled, there’s an unexpected playfulness to Sometimes I Think About Dying that makes a fairly mundane office relationship into a charming romance. Writer-director Rachel Lambert and lead Daisy Ridley capture Fran’s introversion in inventive ways, with score and image to make her daydreams of death more surreal than morbid, with quiet wistfulness of someone that hasn’t quite figured out how to create casual connection. Some viewers might not jive with the way the film focuses more on visual ideas rather than plot, but Sometimes I Think About Dying sweetly depicts social awkwardness and the alluring curiosity a crush can sometimes create.

Genre: Comedy, Drama, Romance

Actor: Ayanna Berkshire, Brittany O'Grady, Daisy Ridley, Dave Merheje, Jeb Berrier, Marcia DeBonis, Megan Stalter, Parvesh Cheena

Director: Rachel Lambert

Rating: PG-13

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, 2024

In the same festival where she showcased her screenwriting chops, Rachel Sennott also showcased her dramatic side in I Used to Be Funny, a difficult drama that garnered less acclaim than Bottoms (2023). It’s understandable– while both films have a witty, gen-Z slant in its comedy, this drama is much harder to balance and heavy to watch, dealing with mental health and PTSD. The non-linear narrative occasionally does make the film feel a tad disjointed as well. However, there’s a care and a warmth from Ally Pankiw’s direction that makes this exploration of Sam’s complex trauma feel heartfelt, and Sennott holds each scene with compelling charisma.

Genre: Comedy, Drama

Actor: Caleb Hearon, Dan Beirne, Dani Kind, Ennis Esmer, Hannah Spear, Jason Jones, Kathy Imrie, Matia Jackett, Miguel Rivas, Olga Petsa, Rachel Sennott, Sabrina Jalees

Director: Ally Pankiw

Rating: NR

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, 2023

The first thing we learn about Dolores Roach is that she is a person of sensation and scandal, a masseuse who, as the newspaper clippings reveal, turned out to be a murderous cannibal serving human flesh to unwitting customers at a local eatery, a la Sweeney Todd. But the series is less about the horrors of the act and more about the woman behind the front. “I was never the blood-hungry sociopath people say I am,” Dolores claims early in the first episode. “I was just some chick in Washington Heights.” In an attempt to humanize Dolores, we’re made privy to the unforgiving circumstances surrounding her case, namely: the desperation of poverty, the relentlessness of discrimination, the brokenness of the criminal justice system, and the inevitability of gentrification, all of which play a crucial role in Dolores’ eventual descent into misdeed and madness. It’s an interesting idea, fleshing out her darkness in a comic tone and pitting it against systemic social problems, but sadly the show never pulls off the balance it needs to become an effective dark comedy. Maybe something was lost when it was adapted from a one-woman play to TV series, but it never really shakes off that amateur approach to telling its delicate story. The heavy-handed narration and the occasional gimmicks overshadow the horrific deaths that occur, and they don’t leave enough space for the story’s relevant themes to aerate and make a significant impact. It’s also not nearly as scandalous nor as sexy as it thinks it is, lacking passion both in its love and murder scenes. They come off scrubbed and squeaky, blunting what could have been, at the very least, a sharp murder thriller. 

Genre: Comedy, Drama

Actor: Alejandro Hernandez, Justina Machado, K. Todd Freeman, Kita Updike

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, 2017

It’s not easy to talk about dysfunctional families, especially when that family is your own. Talking about the reprehensible parenting, but also the love, the understanding behind their neglect, and the few moments when they actually had your back, can be a hard balancing act, which makes Jeannette Walls’ memoir The Glass Castle a challenging one to adapt in film. Because of this, its Hollywood adaptation does have a disjointed tone to it. Woody Harrelson’s Rex initially charms us and his children with his dreams and stories, and time proves his other side, though Jeannette and the audience are asked to forgive him too. It’s not an easy thing, and the ending they reached doesn’t feel totally earned. But it’s still a touching adaptation that captures Walls’ family, warts and all, one that's buoyed up by the strength of its cast.

Genre: Drama

Actor: Alanna Bale, Andrew Shaver, Brenda Kamino, Brie Larson, Brigette Lundy-Paine, Chandler Head, Charlie Shotwell, Chris Gillett, Darrin Baker, Dominic Bogart, Eden Grace Redfield, Ella Anderson, Hamza Haq, Iain Armitage, Joe Pingue, Josh Caras, Kenny Wong, Kyra Harper, Max Greenfield, Naomi Watts, Nathaly Thibault, Olivia Kate Rice, Philippe Hartmann, Robin Bartlett, Sabrina Campilii, Sadie Sink, Samantha Hodhod, Sarah Camacho, Sarah Snook, Shree Crooks, Tessa Mossey, Tyrone Benskin, Vlasta Vrana, Woody Harrelson

Director: Destin Daniel Cretton

Rating: PG-13

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, 2022

Loss can be straightforwardly heartwrenching, but it could also be bewildering, cryptic, and too sudden to even process. New Religion depicts a grieving mother, whose loss of her daughter, and her meet up with an eccentric photographer, causes her to behave strangely. The film goes through the events in a surreal, existential haze, with a skin-crawling scene that reveals the photographer’s nefarious reasons, but the sequences remain inscrutable and the themes and certain characters don’t mesh as well as they could have. New Religion might befuddle viewers just looking for a casual watch, but it’s definitely a thought provoking and promising debut from Keishi Kondo.

Genre: Drama, Horror

Actor: Daiki Nunami, Kaho Seto, Ryuseigun Saionji, Satoshi Oka, Yuki Nagata

Director: Keishi Kondo

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, 2021

There's a mysterious, urgent power to Ear for Eye that survives the project's movement from the stage to the screen. Against moody, bare backgrounds, debbie tucker green's script becomes both story and setting—with words upon words overlapping, being repeated, and being used against each other, expressing the anxiety of entire generations of Black people trying to figure out how to endure all their persecution. What unfortunately <i>doesn't</i> translate well to the screen is the film's editing and its inability to take full advantage of the medium of cinema. Despite the importance of the things being discussed, the end product is a movie that feels like it gets in its own way too much, but still delivers plenty to think about.

Genre: Drama

Actor: Arinzé Kene, Carmen Munroe, Claire Driver, Danielle Vitalis, Danny Sapani, David Gyasi, Demetri Goritsas, Ilirian Bushi, Jade Anouka, Jamal Ajala, Kayla Meikle, Lashana Lynch, Nadine Marshall, Rochelle Rose, Ronkẹ Adékoluẹjo, Sharlene Whyte, Sule Rimi, Tosin Cole

Director: Debbie Tucker Green

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, 2023

Painfully intimate and told with very, very little dialogue, All Dirt Roads Taste of Salt resembles the experience of flipping through a photo book and pausing to admire every page. Which is to say that this is a film that requires not only one's complete attention but—like many other arthouse dramas—a willingness to sit with the mundane until it reveals something more profound. The nearly silent nature of its storytelling can be a little awkward, given how lifelike the rest of the movie is, but one should hopefully get used to the idea that this is an attempt to represent something closer to memory than reality. Whether or not the experience sticks or strikes an emotional chord, it's all beautifully put together, with lush cinematography, impeccably detailed sound design, and thoughtful sequencing of one image after another.

Genre: Drama

Actor: Charleen McClure, Chris Chalk, Kaylee Nicole Johnson, Moses Ingram, Reginald Helms Jr., Sheila Atim, Zainab Jah

Director: Raven Jackson

Rating: PG

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