497 Best Challenging Movies to Watch (Page 31)

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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451. The Prestige, 2006

This movie will first confuse your perception of the narrative with a feud involving the two magicians (played by Hugh Jackman and Christian Bale), but you will soon be hooked by the twists and turns of the plot. The unveiling of the mystery will leave you in awe, however it is the storytelling and the process that Christopher Nolan puts together so beautifully that is the greatest thing about this movie.

Genre: Action, Drama, Mystery, Science Fiction, Thriller

Actor: Andy Serkis, Anthony De Marco, Brian Tahash, Chao Li Chi, Chi Chaoli, Chris Cleveland, Christian Bale, Christopher Neame, Daniel Davis, David Bowie, Edward Hibbert, Enn Reitel, Erin Cipolletti, Ezra Buzzington, Gary Sievers, Hugh Jackman, James Lancaster, James Otis, Jamie Harris, Jim Piddock, Jodi Bianca Wise, John B. Crye, Johnny Liska, Julia Sanford, Kevin Will, Mark Ryan, Michael Caine, Monty Stuart, Piper Perabo, Rebecca Hall, Ricky Jay, Robert W. Arbogast, Rock Anthony, Roger Rees, Ron Perkins, Russ Fega, Samantha Mahurin, Scarlett Johansson, Tim Pilleri, William Morgan Sheppard

Director: Christopher Nolan

Rating: PG-13

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452. Stranger by the Lake, 2013

	
Rarely do we get to see the human body in its natural state in public, mostly limited to nude beaches, but it’s understandably so– beyond the usual social norms, there’s a vulnerability in doing so, a vulnerability that is sometimes taken advantage of. Stranger by the Lake captures the beauty of that vulnerability, with stunning shots that elevate the explicit scenes from being pornographic, but crucially, the film also captures its dangers, namely the increasingly self-destructive risks Franck takes that leads him to a dangerous man. The line between lust and aggression blurs in this film, and understandably, some may take this film to be sex-negative, but Stranger by the Lake is an intriguing slow burn towards its inevitable conclusion.Genre: Drama, Thriller
Actor: Alain Guiraudie, Christophe Paou, François-Renaud Labarthe, Jérôme Chappatte, Mathieu Vervisch, Patrick d'Assumçao, Pierre Deladonchamps
Director: Alain Guiraudie

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453. Femme, 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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454. Electrick Children, 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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455. The Boxer, 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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456. Sometimes I Think About Dying, 2024

	
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, Bree Elrod, 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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457. 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, Mikey Madison, Moses Ingram, Natalie Portman, Noah Jupe, Pruitt Taylor Vince, Y'lan Noel
Rating: TV-MA

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458. 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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459. 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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460. 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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461. 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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462. 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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463. 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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464. 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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465. 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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