473 Best Challenging Movies to Watch (Page 30)

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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436. Lady in the Lake, 2024

	
With such a long career in film, it’s surprising that Natalie Portman has never starred in a television show, except, of course, the occasional voice over and guest appearances. The story that got her to television is Lady in the Lake, the 2019 bestselling crime noir thriller that weaves classic 60s noir with intersectional feminism all through a whodunit plot. Of course, it's no surprise that Portman performs well, and her and co-star Moses Ingram are excellent as mothers seeking change in their respective lives. The comparison between their lives drives home the tragedy of how unfair the odds were stacked against Ingram’s Cleo Johnson. However, the way director Alma Har'el alternates between lives is clunky and sometimes even confusing, even if it's in hopes to bring the original novel’s POV shifts onto the screen. The source material is ambitious, daring, and a worthy vehicle for both Portman and Ingram, so it's disappointing to see Lady in the Lake already sputtering at the start.Genre: Crime, Drama
Actor: Brett Gelman, Byron Bowers, Moses Ingram, Natalie Portman, Y'lan Noel
Rating: TV-MA

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437. I Used to Be Funny, 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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438. A Killer Paradox, 2024

	
Life can be funny sometimes, with the way accidents can lead us to what would make the entirety of our lives. Usually, these accidents lead us to a new career, maybe the love of our life, and sometimes a new life path altogether, but for recently discharged Lee Tang in A Killer Paradox, it leads to finding that his talent is killing evildoers, accidentally or otherwise. It’s funny to see Lee accidentally getting away with murder and the way his imagination conceives of his serial killer victims, but the show also gets into intriguing thought experiments about the morality of his actions, as well as the way we try to reconcile the tragedy of a lost life, with the terrible consequences of the actions they did with their lives. It’s enjoyable, with the great cast and the unique cinematography, but the writing, structure, and thriller aspects fail to maximize what’s so interesting about A Killer Paradox.Genre: Comedy, Crime, Mystery
Actor: Choi Woo-shik, Lee Hee-jun, Son Suk-ku
Director: Lee Chang-hee
Rating: TV-MA

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439. The Horror of Dolores Roach, 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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440. The Glass Castle, 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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441. Shahmaran, 2023

As a fantasy romance series, Shahmaran feels like it could be something more. Blending in Turkish folklore and a steamy romance, the show is based on the legend of the titular feminine mythic creature and a prophecy promising Shahmaran’s return, if only they’re willing to make the same sacrifice she did long ago. There’s something here about coming to terms with your past, whether that be your heritage or your family’s history of mental illness and trauma. However, the show’s slow pace can dissuade viewers, and the series can’t help itself from leaning too far into the drama of it all.

Genre: Action & Adventure, Drama, Mystery, Sci-Fi & Fantasy

Actor: Burak Deniz, Mahir Günşiray, Mert Ramazan Demir, Mustafa Uğurlu, Serenay Sarıkaya

Director: Umur Turagay

Rating: TV-MA

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442. New Religion, 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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443. ear for eye, 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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444. The Lions of Sicily, 2023

In the previous centuries, people were born into and died without ever being able to change their status. Nobles remained nobles and peasants remained peasants. But around the Renaissance, the idea of commerce and education allowed some leeway for men to reach a higher station, and for the Florios of Sicily, they’re able to reach higher spaces through the sheer force of will. This is an interesting idea, and The Lions of Sicily by Stefania Auci is able to capture it, but its show counterpart falters in depicting this. The sets and costumes are up to par, but the screenplay is unable to balance between the backstories, with the episode slipping confusedly in and between timelines.

Genre: Drama

Actor: Donatella Finocchiaro, Eduardo Scarpetta, Michele Riondino, Miriam Leone, Vinicio Marchioni

Director: Paolo Genovese

Rating: TV-MA

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445. All Dirt Roads Taste of Salt, 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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446. THE LEGEND & BUTTERFLY, 2023

Made to commemorate Toei Studio’s 70th anniversary, The Legend & Butterfly seemed like a good choice for this purpose. As a historical epic about the first Great Unifier of Japan, the film could have enabled the production company to show off their studio’s best in production design, set pieces, costumes, and score, through a familiar story Japanese audiences would care about. And with Nohime having a near blank slate in history, it gives enough creative freedom for the team to craft a heartrending romance. While the design aspects definitely succeeded, the romance did not. On top of this, the film’s focus on the romance takes away time, effort, and emotional resonance from the large-scale spectacular war battles that epics like these are known for.

Genre: Drama, History, Romance

Actor: Ai Mikami, Daisuke Honda, Haruka Ayase, Hideaki Ito, Hio Miyazawa, Hirotaro Honda, Ichikawa Somegorō VIII, Jun Hashimoto, Kinya Kitaoji, Kokoro Morita, Manabu Hamada, Mansaku Ikeuchi, Masato Wada, Miki Nakatani, Shuichiro Masuda, Takuma Otoo, Takumi Saitoh, Takuya Kimura, Toshinori Omi, Tsutomu Takahashi

Director: Keishi Otomo

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447. The Beast in the Jungle, 2023

	
Transporting the Henry James novella to the nightclub, The Beast in the Jungle turns the Edwardian era story into a surreal, escapist drama spanning the last decades of the 20th century. As John and May wait for that all-important event, they lose the importance of everything else, like love, friendship, and family, all to the decadence they only acknowledge as patience. This concept paired with the visuals are interesting, especially since the film also makes the viewer wait with them, drawing out the existential frustration, the fear of a life not lived, and the self-absorption, but the film struggles with the historical events, haphazardly inserting tragedies like the AIDS epidemic for what seems to be no reason.Genre: Drama
Actor: Anaïs Demoustier, Bachir Tlili, Béatrice Dalle, Mara Taquin, Martin Vischer, Tom Mercier
Director: Patric Chiha

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448. Thank You, I'm Sorry, 2023

Parenting is hard by itself, but it’s moreso hard when done alone, especially if there was supposed to be a partner alongside the journey. Thank You, I’m Sorry depicts this through Sara, who has to deal with her husband’s absence and difficulties in connecting with her husband’s family in his stead, on top of her pregnancy, but it’s her connection with her estranged sister Linda that can make or break her journey. The dynamic between the sisters is what drives the film. Sanna Sundqvist and Charlotta Björck manage to depict the strained yet clearly loving relationships naturally, and it’s lovely to see the mundane ways they reestablish their bond. It’s a unique story, though it does feel rushed and some of the humor can be totally off-putting.

Genre: Comedy, Drama

Actor: Charlotta Björck, Ia Langhammer, Jonatan Rodriguez, Sanna Sundqvist, Ville Virtanen

Director: Lisa Aschan

Rating: PG-13

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449. Stopmotion, 2024

	
The act of creation is difficult. It’s hard enough to bring to life one’s own ideas, but when one was taught, inherited, and directly molded by their parents, it can be hard to break free and figure out one’s own style. Stopmotion uses the type of animation to directly visualize the dynamic– a literal puppet being controlled by a child, a metaphorical puppet, controlled by a parent puppet master, in two different ways– and it’s a unique, brilliant premise made so unsettling with writer-director Robert Morgan’s signature animated style. While the film doesn’t neatly stitch its multiple layers together, Stopmotion is an eerie, chilling debut with original style.Genre: Horror
Actor: Aisling Franciosi, Bridgitta Roy, Caoilinn Springall, James Swanton, Jaz Hutchins, Joshua J. Parker, Nicola Alexis, Stella Gonet, Therica Wilson-Read, Tom York
Director: Robert Morgan
Rating: R

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450. Rain Dogs, 2023

Whether or not its intentionally messy, erratically paced style resonates with you, there's something undeniably special about having a show like Rain Dogs in our current television landscape. Almost aggressively opposed to the idea of comfort viewing and easily marketable drama, the series deals with characters who are at rock bottom for all eight episodes. There's a particular restlessness to its storytelling that keeps it thoroughly unpredictable, and allows Daisy May Cooper and Jack Farthing to play razor-sharp, open-hearted roles without any pretension whatsoever. But Rain Dogs' unique personality also means it can be especially challenging to latch on to its story—especially when the momentum is rarely carried over from one episode to the next. We become trapped in the show's central toxic friendship to the point of overemphasis. And that's a rare, valuable thing, but it can also be much too frustrating.

Genre: Comedy, Drama

Actor: Daisy May Cooper, Fleur Tashjian, Jack Farthing, Ronkẹ Adékoluẹjo

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