306 Best Challenging Movies to Watch (Page 5)

Staff & contributors

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.

The Kings of the World is a surreal coming-of-age movie that follows Rá, Culebro, Sere, Winny, and Nano, street kids who are on their way to claim land that’s rightfully theirs. Their one goal is to finally make a home after living without one for so long, but they’re hindered by the inevitable tragedies that befall kids of their kind: impoverished, alone, and abandoned.

The title is ironic, but it also hints at their state of mind: these boys are unstoppable, rabble-rousers who live like there’s no tomorrow. They tear down private property and invade inns not out of spite, necessarily, but out of a knowledge that whatever they do they’re gonna be put down anyway, so they might as well live without rules.

Tackling powerful themes like land restitution and youth neglect, The Kings of the World is one of the most agonizing movies you'll ever see. It’s also Colombia’s official Best Foreign Language Film entry in the 2022 Academy Awards.

Genre: Adventure, Drama

Actor: Brahian Acevedo, Carlos Andrés Castañeda, Cristian Campaña, Cristian David Duque, Davison Florez

Director: Laura Mora

Rating: TV-MA

Ryan Gosling plays a Jewish Neo-Nazi in this extremely riveting window into the definition of inner conflict. It is a prime example of how character development should be done and it put Gosling on the map for me. He starts out as an exemplary student in Hebrew school until he starts questioning his teachings and exploring alternative ideologies, leading him to the neo-Nazi movement. Won the Grand Jury Prize at Sundance

Genre: Drama

Actor: A.D. Miles, Billy Zane, Chuck Ardezzone, David Bailey, Dean Strober, Ebon Moss-Bachrach, Elizabeth Reaser, Garret Dillahunt, Glenn Fitzgerald, Heather Goldenhersh, Henry Bean, Joel Garland, Joel Marsh Garland, Jordan Lage, Joshua Harto, Kris Eivers, Lucille Patton, Michael Marcus, Michael Port, Peter Meadows, Ronald Guttman, Ryan Gosling, Sascha Knopf, Sig Libowitz, Summer Phoenix, Theresa Russell, Tibor Feldman, Tommy Nohilly

Director: Henry Bean

Rating: R

Challenging, strange, and utterly captivating from start to finish, Sanctuary takes the relationship between a pathetic, wealthy man and a desperate, plucky young woman—a relationship built on consensual acts of sexual humiliation—and makes it so much more dynamic and entertaining than it has any right to be. The film takes place entirely in one hotel suite over the course of one night, becoming a series of increasingly absurd psychological scenarios, as the characters wrestle over ideas of power, shame, and identity by concealing and roleplaying various parts of themselves. It's a wild take on several different genres that director Zachary Wigon is able to effortlessly weave together with excellent pacing, stunning visuals, and two truly committed performances from Christopher Abbott and a wonderfully unhinged Margaret Qualley.

Genre: Comedy, Drama, Romance, Thriller

Actor: Christopher Abbott, Margaret Qualley

Director: Zachary Wigon

A very intelligent and nuanced movie that relentlessly asks unpleasant questions. It's a story about a woman seeking freedom by turning away from her own family and finding something she did not expect. The main character of the movie, Martha, is taken in by a cult and the movie depicts how this experience shapes and warps her life, thoughts, and actions. The time she spent with the cult ultimately also shapes her own personality, which raises questions about her identity and the place she now fits in. Every actor is well cast, and especially Elizabeth Olsen (playing Martha) puts on a stand-out performance, which proves that she is an actor to watch out for in the years to come.

Genre: Drama, Mystery, Thriller

Actor: Adam David Thompson, Allen McCullough, Brady Corbet, Christopher Abbott, Elizabeth Olsen, Gregg Burton, Hugh Dancy, John Hawkes, Julia Garner, Lauren Molina, Louisa Krause, Maria Dizzia, Sarah Paulson, Tobias Segal

Director: Sean Durkin

Rating: R

Before The Silence of the Lambs and Anthony Hopkins’ Hannibal, there was Manhunter and Brian Cox’s deeply unnerving Dr. Lecktor. Michael Mann’s neon-lit serial-killer thriller follows Will Graham (William Petersen), a retired FBI agent lured back to work by a psychotic mass murderer whom no one at the Bureau can catch. But Will has something no one else on the force does: he was so committed to tracking down the now-imprisoned Lecktor that he developed an ability to warp his mind into that of a deranged killer, seeing a kind of logic in their madness that allows him to hunt them down. 

While that’s a professional superpower of sorts, it’s also a point of insecurity and a source of deep torture for Will, who struggles with the burden of his extraordinary empathy. Manhunter is thus a different kind of psychological thriller: while its dive into the depraved minds of Lecktor and the Tooth Fairy is certainly disturbing, it’s the obsessive, sanity-smashing effect the investigation has on Will that is most terrifying. Add to that Dante Spinotti’s impossibly vivid cinematography, Tom Noonan’s shudder-inducing performance as the voyeuristic Tooth Fairy, and the film’s surprisingly layered treatment of the murderer, and this is the serial-killer movie to end all others.

Genre: Crime, Drama, Horror, Thriller

Actor: Alexandra Neil, Annie McEnroe, Benjamin Hendrickson, Bill Cwikowski, Bill Smitrovich, Brian Cox, Chris Elliott, Cynthia Chvatal, Dan Butler, David Allen Brooks, David Seaman, Dennis Farina, Elisabeth Ryall, Frankie Faison, Garcelle Beauvais, Jim Zubiena, Joan Allen, Joanne Camp, John Posey, Ken Colquitt, Kim Greist, Kin Shriner, LA Winters, Marshall Bell, Michael D. Roberts, Michael Talbott, Michele Shay, Norman Snow, Pat Williams, Patricia Charbonneau, Paul Perri, Peter Maloney, Robin Moseley, Stephen Lang, Tom Noonan, William Petersen

Director: Michael Mann

How do you get rid of an irremovable stain? In Lodge Kerrigan’s psychological thriller, characters shave the dirt off in hopes of returning things to their original pristine state. In the process of doing so, however, permanent damage is incurred, which begs the question: is the eradication of filth correspond to cleansing?

Through erratic editing and an unsettling sound design, not only does Clean, Shaven put its audience in the disturbed mind of the protagonist Peter Winter, it also effectively depicts his struggle (and inability) to retain sanity amidst a prejudiced society. The film contrasts post-Cold War paranoia with the nobility of paternal love, and finds tragedy in Peter’s futile attempts to prove his “cleanliness” in a world intent to brand him as dirty.

Genre: Crime, Drama, Thriller

Actor: Eliot Rockett, Ismael Ramirez, J. Dixon Byrne, Jennifer MacDonald, Karen MacDonald, Molly Castelloe, Peter Greene

Director: Lodge Kerrigan

A harrowing family loss sets off a poetic exploration of grief in this experimental film from Haitian-Canadian filmmaker Miryam Charles. The focus of the movie is Charles’ own cousin, who was found murdered in her Connecticut bedroom in 2008. Rather than let her cousin’s life remain frozen at that point in time, Charles unmoors her film from the cold realities of time and space to suggest new perspectives on the girl’s past and imagine a future that never came. While events like the family’s decision to move to the US are recast as portends of tragedy, there’s also deep generosity in the movie’s ghost story — such as the joyous scenes it depicts from a mother-daughter trip to the family’s home country of Haiti, a trip that never actually took place.

It’s not always easy to discern where or when we’re at in its liberal toggling between time and space, but once Cette Maison establishes its unconventional visual language, everything comes into poignant focus. Given the reality on which it’s based, this is undoubtedly a heartbreaking watch, but the way Charles’ movie evokes the ability of imagination to both deepen and assuage the pain of grief is nothing short of revelatory.

Genre: Crime, Drama, Fantasy

Actor: Ève Duranceau, Nadine Jean

Director: Miryam Charles

Bad Lieutenant is no misnomer: Harvey Keitel’s policeman really is one of NYPD’s worst. Already corrupt, abrasive, and abusive at the film’s outset, the movie chronicles his coked-out descent into total depravity after he’s called to investigate a heinous crime amid rapidly worsening personal circumstances. The brilliance of Bad Lieutenant is therefore a counterintuitive one: as awful as the Lieutenant is, we can’t help but feel emotionally involved because, in Keitel’s bravura performance, we can see the glint of pain — and thus of a person — within.

Always one for provocation, director Abel Ferrara pushes our empathy to — and maybe even beyond — its natural limits, only to break with the film’s hitherto unrelenting grit and dangle the glinting possibility of transcendent redemption in front of us. Anyone familiar with Catholic guilt cinema (movies like Martin Scorsese’s Who’s That Knocking At My Door and Mean Streets) will instantly recognize the same undercurrent running through Bad Lieutenant — even if Ferrara takes the idea of juxtaposing the profane with the sacred to the extreme here.

Genre: Crime, Drama

Actor: Bianca Hunter, Bo Dietl, Dana Dee, Darryl Strawberry, Eddie Daniels, Frank Adonis, Frankie Thorn, Gene Canfield, Harvey Keitel, Iraida Polanco, Jaime Sánchez, John Steven Jones, Leonard L. Thomas, Minnie Gentry, Paul Calderon, Paul Hipp, Peggy Gormley, Penelope Allen, Phil Neilson, Stella Keitel, Victor Argo, Vincent Laresca, Zoë Lund

Director: Abel Ferrara

Based on a true story, The Whistleblower is the biography of a once Nebraskan police officer who volunteers for the U.N. peacekeeping mission in post-war Bosnia. Once there, she uncovers a human trafficking scandal involving peacekeeping officials, and finds herself alone against a hostile system in a devastated country. Rachel Weisz plays the whistleblower in a powerful lead role, but the true star of the movie is its director, Larysa Kondracki, who thanks to near documentary-style film-making delivers a perfectly executed political thriller with utmost authenticity.

Genre: Crime, Drama, Mystery, Thriller

Actor: Adriana Butoi, Alexandru Potocean, Alin Panc, Anca Androne, Anna Schafer, Benedict Cumberbatch, Catherine McNally, Coca Bloos, Danny John-Jules, David Hewlett, David Strathairn, Dorotheea Petre, Florin Busuioc, Geoffrey Pounsett, Jeanette Hain, Liam Cunningham, Luke Treadaway, Monica Bellucci, Nikolaj Lie Kaas, Paul Jerricho, Paula Schramm, Pilou Asbæk, Rachel Weisz, Radu Bânzaru, Rayisa Kondracki, Rosabell Laurenti Sellers, Roxana Condurache, Roxana Guttman, Sergej Trifunović, Stuart Graham, Vanessa Redgrave, Victoria Raileanu, Vlad Ivanov, William Hope

Director: Larysa Kondracki

Rating: R

There are a striking number of similarities between Priscilla and director Sofia Coppola’s earlier offering, Marie Antoinette: both revolve around 14-year-old girls hand-picked to be partners to more powerful men in long-unconsummated relationships, and both girls are emotionally cut adrift and forced to live in gilded cages. But where Coppola’s Barbie-pink historical biopic is punkily anachronistic and riotous, Priscilla is a far more muted affair. There are no wild parties at Graceland as there were at Versailles; instead, Priscilla’s emotional isolation, thousands of miles away from her family, is made disconcertingly clear in shots of the infatuated teenager (played by Cailee Spaeny) anxiously ruminating alone in endless lavish rooms while the decade-older King (Jacob Elordi) plays away. Elvis’ emotional manipulation of Priscilla is conveyed subtly but inescapably — and the full sickening, insidious effect comes to the fore thanks to Spaeny’s astonishing performance. Based on Priscilla Presley’s own memoir, this is a bubble-bursting biopic, and it’s so compelling and painfully immersive that we never feel, even for a moment, like we’re watching the B side — instead, Spaeny and Coppola convincingly assert that this was the real story all along.

Genre: Drama, Romance

Actor: Alanis Peart, Ari Cohen, Cailee Spaeny, Conni Miu, Dagmara Domińczyk, Dan Abramovici, Dan Beirne, Deanna Jarvis, E. Fegan DeCordova, Gwynne Phillips, Jacob Elordi, Jorja Cadence, Josette Halpert, Kamilla Kowal, Kelaiah Guiel, Kelly Penner, Luke Humphrey, Lynne Griffin, Mary Kelly, Olivia Barrett, R Austin Ball, Rodrigo Fernandez-Stoll, Sarah Dodd, Stephanie Moore, Stephanie Moran, Tim Dowler-Coltman, Tim Post

Director: Sofia Coppola

Rating: R

Set against the backdrop of the Algerian Civil War in the 1990s, the film follows Nedjma, a young fashion student, as she navigates the challenges of pursuing her dreams while living under strict societal and religious constraints. Gripping and emotionally charged, the film paints a vivid picture of the oppressive climate and the courageous women who refuse to be silenced. The performances are outstanding, particularly Lyna Khoudri's portrayal of Nedjma, who brings a compelling blend of vulnerability and determination to her character. Director Mounia Meddour's storytelling is powerful and thought-provoking, shining a light on the resilience of women in the face of adversity and the importance of artistic expression as a form of resistance. 

Genre: Drama

Actor: Ahmed Benaissa, Aida Guechoud, Amira Hilda Douaouda, Khaled Benaissa, Lyna Khoudri, Nadia Kaci, Samir Elhakim, Shirine Boutella, Yasin Houicha, Zahra Doumandji

Director: Mounia Meddour