497 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.

There are moments in our childhood that we deeply regret, even if we didn’t know better, even if innocence can excuse us, and even if we weren’t the ones primarily responsible for the mistake. The memory of it can be haunting, but none has been as devastating as the memory depicted in Louis Malle’s semi-autobiographical period drama Au Revoir les Enfants. Malle brings us to the boarding school rhythms with ease, straightforwardly depicting it as is, but with the camera and the sequencing recognizant of the implications. With the natural dynamic between the unthinking Julien (Malle’s younger self) and the alert and afraid Jean formed through subtle moments, Au Revoir les Enfants culminates into the heartbreaking coming-of-age moment that Malle personally lived through in World War II.

Genre: Drama, War

Actor: Arnaud Henriet, Francine Racette, François Berléand, François Négret, Gaspard Manesse, Irène Jacob, Luc Etienne, Pascal Rivet, Peter Fitz, Philippe Morier-Genoud, Raphael Fejtö, René Bouloc, Sergio Kato, Stanislas Carré de Malberg

Director: Louis Malle

Rating: PG

Art is a hobby for most people, but for musician Jon Batiste and writer Suleika Jaouad, art is part and parcel of this thing called life. Of course, it’s part of their work, and it’s how they make a livelihood, but it’s more than that– it’s almost a spiritual ritual they cling to, especially when Jaouad finds out that her leukemia has returned. American Symphony mainly depicts the creation of said orchestral work, but director Matthew Heineman translates the symphony into cinematic form, culminating in a performance played over the intimate moments between Batiste and Jaouad. It’s not just a documentary of a performance, but a documentary about art, about creation despite life’s pains, perhaps to survive life’s pains. It’s a powerful work that makes it easy to believe in art as imperative for life, and vice versa.

Genre: Documentary, Music

Actor: Anna Wintour, Billie Eilish, James Taylor, Jon Batiste, Jonathan Dinklage, Justin Bieber, Lenny Kravitz, Louis Cato, Questlove, Simon Helberg, Stephen Colbert, Stevie Wonder, Suleika Jaouad, Trevor Noah

Director: Matthew Heineman

Rating: PG-13

The Sweet Hereafter is the kind of movie that feels very different from the one you might imagine when reading the plot synopsis. The tragic accident at its center doesn’t form a dramatic crescendo as you might be primed to expect — and, despite revolving around a lawsuit, this is no courtroom drama. Instead, the ironically titled The Sweet Hereafter deals with the messy, difficult emotions that come with grief, survival, and blame in the aftermath of a bus crash, with the film largely taking place in a snowy Canadian town rent apart by the loss of nearly all its children in the accident. Ian Holm plays the out-of-town lawyer battling to unite the bereft parents behind a class action lawsuit, all while struggling to deal with the quasi-loss of his own drug-dependent daughter. Non-linear chronology means the before-the-crash and the after intermingle, scene after scene; it’s an unorthodox remix of the way we’re used to seeing this kind of story unfold, but it allows the movie to home in on the complexity of the community’s pain. Unsparing performances, haunting music, and meditative cinematography plunge us into it all, recreating the terrible iciness of grief in a way that is difficult to shake off.

Genre: Drama

Actor: Alberta Watson, Allegra Denton, Arsinée Khanjian, Brooke Johnson, Bruce Greenwood, David Hemblen, Devon Finn, Earl Pastko, Gabrielle Rose, Ian Holm, Kirsten Kieferle, Marc Donato, Maury Chaykin, Mychael Danna, Peter Donaldson, Sarah Polley, Sarah Rosen Fruitman, Simon Baker, Stephanie Morgenstern, Tom McCamus

Director: Atom Egoyan

Rating: R

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, Gusmano Cesaretti, Jim Zubiena, Joan Allen, Joanne Camp, John Posey, Ken Colquitt, Kim Greist, Kin Shriner, Kristin Holby, 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: Alice Levitt, Eliot Rockett, Ismael Ramirez, J. Dixon Byrne, Jennifer MacDonald, Karen MacDonald, Molly Castelloe, Peter Greene, Peter Lucas, Rob Benevides, Robert Albert

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, Bob Murphy, Brian McElroy, Dana Dee, Darryl Strawberry, Ed Kovens, Eddie Daniels, Frank Adonis, Frankie Acciarito, Frankie Thorn, G. Elvis Phillips, Gene Canfield, Harvey Keitel, Heather Bracken, Iraida Polanco, Jaime Sánchez, John Steven Jones, Larry Mullane, Leonard L. Thomas, Minnie Gentry, Nicholas De Cegli, Paul Calderon, Paul Hipp, Peggy Gormley, Penelope Allen, Phil Neilson, Robin Burrows, Stella Keitel, Stephen Chen, Victor Argo, Victoria Bastel, 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, Bryan Jardine, Catherine McNally, Coca Bloos, Danny John-Jules, David Hewlett, David Strathairn, Dorotheea Petre, Florin Busuioc, Geoffrey Pounsett, Ion Sapdaru, Ionut Grama, 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 is nothing quite like The Substance right now. It’s unsubtle, it’s provocative, and its satirical humor can be a hit or miss for some viewers, but it strikes at the one thing that’s fundamental to everyone, that can make or break their lives, yet that is rarely given grace and consideration– that is the body. Legions of people have yearned for youth and beauty, but The Substance systematically outlines how much these have been intertwined with our livelihoods, opportunities, and identities, and how other entities would capitalize on this yearning and push many of us to take that out, suck that out, literally, from ourselves. The Substance does this all with insane, frenetic energy.

Genre: Drama, Horror, Science Fiction, Thriller

Actor: Andrew Desmond, Ashley Lambert, Christian Erickson, Coralie Fargeat, Demi Moore, Dennis Quaid, Edward Hamilton-Clark, Gore Abrams, Gregory Defleur, Hugo Diego Garcia, Jonathon Carley, Margaret Qualley, Matthew Géczy, Matthew Luret, Michael Corbett, Nathan Rippy, Olivier Raynal, Oscar Lesage, Philip Schurer, Ranjani Brow, Robin Greer, Shane Sweet, Stephen Apostolina, Tiffany Hofstetter, Tom Morton, Vincent Colombe, Yann Bean

Director: Coralie Fargeat

Rating: R

In the first twenty minutes, The Remarkable Life of Ibelin seemed to be quite unremarkable, with the usual way a biographical documentary would go, that is, loved ones waxing poetic about how great the dead person was in life. But the documentary takes this to introduce Ibelin the same way his parents discovered the online life Mats Steen lived. It’s a unique documentary, mixing in the usual home videos with the animated gameplay of the archived life Steen lived in Ibelin, but it’s grounded by, and somewhat co-created through the words Steen himself typed about his life as a disabled man, and the game history he shared with the community he formed online. The Remarkable Life of Ibelin ends up being quite a remarkable depiction of living online, that feels much more honest, human, and creative than the condescending or cautious narratives we’ve previously heard about the online world.

Genre: Animation, Documentary

Actor: Elena Pitsiaeli, Kelsey Ellison, Mats Steen, Paul Wild, Zoe Croft

Director: Benjamin Ree

Rating: PG-13