306 Best Challenging Movies to Watch (Page 4)

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.

Clocking in at just under four hours, Hu Bo's first and last feature film—before his tragic death at the age of 29—is a sprawling indictment of a country that the filmmaker must have viewed as positively hostile and suffocating. Following several characters whose paths intersect as they try to escape their current circumstances, An Elephant Sitting Still creates a truly oppressive atmosphere that may not lead you to the answers you expect, but it should leave you feeling haunted for a long, long time. Beautifully scored, shot, and acted, Hu's film offers practically no hope but it keeps on moving with a sense of freedom and determination all its own. This is as honest a film can get; Hu has left behind a moving legacy.

Genre: Crime, Drama

Actor: Li Congxi, Peng Yuchang, Wang Yuwen, Zhang Yu, Zhao Tao, Zhu Yan Man Zi, Zhu Yanmanzi, Zhu-Yan Manzi

Director: Hu Bo

To Leslie follows the eponymous Leslie (Andrea Riseborough), a Southern woman who finds herself at the bottom of the barrel after finally using up every penny of her $190k lottery win. Out of work, friends, and family, she drowns herself in alcohol—that is until a kind soul in the form of motel owner Sweeney (Marc Maron) takes her in and gives her a shot.

To Leslie starts off a bit slow, and its premise may seem like it’ll give way to weepiness, but it’s worth sticking by till the end. The film only gets better, especially with the arrival of Maron, whose presence lends the film a much-needed buoyancy. It's also worth noting that unlike many of its kind, To Leslie avoids the poverty porn trap by depicting issues like addiction and indigence with nuance, honesty, and humanity.

Genre: Crime, Drama

Actor: Alan Trong, Alan Wells, Allison Janney, Andre Royo, Andrea Riseborough, Arabella Grant, Blake Robbins, Brandee Steger, Catfish Jean, Chris Coy, Derek Phillips, Drew Youngblood, Jack O'Connor, James Landry Hébert, Jeanette O'Connor, John Gilbert, Juan Carlos Cantu, Lauren Letherer, Mac Brandt, Maggie Carney, Marc Maron, Matt Lauria, Micah Fitzgerald, Owen Teague, Paula Rhodes, Pramod Kumar, Scott Peat, Scott Subiono, Sewell Whitney, Stephanie Wong, Stephen Root, Tom Virtue

Director: Michael Morris

Rating: R

Named for all the connections that form a functioning society, Threads is a harrowing look at what might happen when those ties are rent apart by nuclear war. This British TV movie — released during the Cold War — so violently seized on the nuclear anxieties of the time that its premiere was dubbed “the night the country didn’t sleep.” Depressingly, it hasn’t lost that initial resonance, and so it remains a panic attack-inducing watch.

Threads begins in the kitchen-sink vein of a Ken Loach movie. In the northern industrial town of Sheffield, a young couple from different social classes (Reece Dinsdale and Karen Meagher) discover they’re about to be parents — but looming above their small-scale drama are the clouds of war, as televisions and radios blare out the details of escalating tensions between the US and the USSR. And then, it happens: the town is strategically bombed, and Threads unfurls into an unrelenting nightmare. In the documentary-like approach that follows, it spares no graphic or emotional detail, charting both the personal devastation caused by the bomb and the annihilating impact of the nuclear holocaust on all the vital infrastructure we take for granted. In short, one of the bleakest, most terrifying movies ever made.

Genre: Drama, Horror, Science Fiction, War

Actor: Ashley Barker, Brian Grellis, David Brierly, Dean Williamson, Ed Bishop, Harry Beety, Henry Moxon, Jane Hazlegrove, Joe Belcher, Karen Meagher, Lesley Judd, Maggie Ford, Michael O'Hagan, Nat Jackley, Patrick Allen, Peter Faulkner, Phil Rose, Reece Dinsdale, Richard Albrecht, Rita May, Ruth Holden, Steve Halliwell, Ted Beyer

Director: Mick Jackson

This poetic memoir by the late director Terence Davies opens with a tracking shot that takes us down a rainy, dilapidated Liverpool street, finally settling on the wet staircase of a roofless house as three audio tracks morph into one another: a Nat King Cole song, dialogue from a movie, and, finally, a boy calling for his mother. Just as we hear the latter, the shot of the exposed staircase dissolves, taking us into the past to reveal the owner of the voice sitting in the same spot — only now, the stairs are dry, the roof restored. 

The scene perfectly encapsulates the film: it's a dreamlike pool of sensory recollections from that lonely boy’s childhood, assembled according to the strange logic of memory. Music and movie dialogue echo across the film as we watch snapshots from Bud’s (Leigh McCormack, playing a proxy of Davies) early years. Though most of the memories radiate warmth — Christmases with family, euphoric cinema trips — a note of melancholy tinges these blissful recollections. Callously cruel schoolmates, desperate church prayers, and instantly rueful stolen glances jar against the nostalgia and let us know that something dark is coming. Intensely, painfully intimate, this is one of the best and most unbearably sad evocations of memory in cinema.

Genre: Drama

Actor: Anthony Watson, Ayse Owens, Leigh McCormack, Marjorie Yates, Mark Heath, Nicholas Lamont, Patricia Morison, Peter Ivatts, Tina Malone

Director: Terence Davies

Such a good movie. The start is reminiscent of great, funny coming-of-age stories. However, a violent event quickly takes place and The Hate U Give becomes a powerful comment on police brutality in America, institutional oppression, and what it's like to be from a marginalized community but try to find your place in the world. But at the end, it's a 'movie' movie, directed by George Tillman Jr. who made the Barbershop movies and Men of Honor (with De Niro).

Genre: Crime, Drama

Actor: Abby Glover, Al Mitchell, Algee Smith, Amandla Stenberg, Andrene Ward-Hammond, Anthony Mackie, Brian Lafontaine, Common, Dominique Fishback, Drew Starkey, Dustin Lewis, Issa Rae, Iyana Halley, K.J. Apa, Kai N. Ture, Karan Kendrick, Lamar Johnson, Lonnie Rashid Lynn Jr., Marcia Wright, Megan Lawless, Milton Saul, Myles Evans, Rayven Symone Ferrell, Regina Hall, Rhonda Johnson Dents, Russell Hornsby, Sabrina Carpenter, Shay Mack, Susan Santiago, Tanya Christiansen, TJ Wright, Tony Vaughn

Director: George Tillman Jr.

Rating: PG-13

, 2021

In the first few minutes of Mass, hushed tones, solemn movements, and awkwardly averted eyes hint at an unspoken tragedy that haunts everyone in the film. The four main characters discuss it during a sit-down, but even then it remains unspeakable; such is the dedication of first-time full-length director Fran Kranz in depicting the reality of tragic events. Not much is done in the way of plot twists and shocks, but in place of those, Mass makes clever use of close-up shots and unmoving settings to portray the privacy and paralysis of grief. For this reason, Mass often feels like a masterful play brought to life, but also more than that, a brilliant portrait of healing—or at the very least, coping with the everlasting aftermath of loss. 

Genre: Drama

Actor: Ann Dowd, Breeda Wool, Jason Isaacs, Martha Plimpton, Michelle N. Carter, Reed Birney

Director: Fran Kranz

La Cérémonie is the kind of thriller you can watch repeatedly and glean new insight from each time. Right from its first scene, there’s something puzzling about the buttoned-up Sophie (Sandrine Bonnaire) that narrows your focus and pulls you in. What’s remarkable is that, even after the secret Sophie's keeping that seems to explain her strangeness is revealed, our intrigue never dips. Director Claude Chabrol and his cast construct a gripping twin character study and biting social commentary around that initial hook, as Sophie finds a kindred spirit in the equally uncanny Jeanne (Isabelle Huppert), who opens her eyes to the slyly patronizing way Sophie’s employers treat her.

The film’s study of class relations is always subtle, never veering into over-pronounced territory. That much is clear from the fact that, although some of Sophie’s employer’s family are quite likable, you still understand the ways they’re inextricably embroiled in the film’s quiet indictment of the power dynamics that rule this lofty mansion. More nuance comes by way of the strikingly nonchalant ways evil is depicted in La Cérémonie — just another example of the movie turning something expected (violence is foreshadowed early on) into something that remains viscerally shocking, no matter how many times you watch it.

Genre: Drama, Thriller

Actor: Christophe Lemoine, David Gabison, Dominique Frot, Isabelle Huppert, Jacqueline Bisset, Jean-François Perrier, Jean-Pierre Cassel, Julien Rochefort, Sandrine Bonnaire, Valentin Merlet, Virginie Ledoyen, Yves Verhoeven

Director: Claude Chabrol

Rating: NR

There is footage and coverage to prove that the pizza bomber story actually happened but watching Evil Genius: The True Story of America's Most Diabolical Bank Heist everything is so intriguing it is almost impossible to believe. A pizza-delivery guy shows up to rob a bank with what he says is a bomb secured around his neck, something that he claims is part of a treasure hunt. By robbing the bank, he will unlock the next set of clues that will allow him to defuse the bomb. Bank tellers comply but on the way out he is suddenly arrested by the police, who doubt his claims, handcuff him and keep him at a distance. The device he has around his neck then starts beeping. What follows is one of the most unusual investigations ever led by security forces, brilliantly framed by executive producers Duplass brothers. A perfect follow-up to their other amazing True-crime Netflix collaboration, Wild Wild Country, it’s a tight 4-episodes that is equally terrifying and intriguing.

Genre: Documentary

Director: Barbara Schroeder, Trey Borzillieri

Rating: Not Rated

Martin Scorsese — plus screenwriter Paul Schrader, editor Thelma Schoonmaker, and cinematographer Robert Richardson — reimagine nocturnal New York City as an eternally flaming circle of hell in this darkly funny fever dream. Frank Pierce (Nicolas Cage) is an insomniac paramedic who’s haunted by the ghosts of all the lives he couldn’t save and is on a nightmarish run of losing every patient he tries to help. There’s no respite for him anywhere; he’s so burnt out he begs to be fired, but the city is so desperate they won’t let him leave their tired ranks of medics, who are mostly jaded, sometimes sadistic, and yet still addicted to the euphoric high of saving a life.

As Frank is pushed ever closer to breaking point, the film takes on the hallucinatory qualities of his perspective, the cinematography growing feverish and the editing powered by a wild, manic energy. What stops the movie from feeling like a spiral into actual hell is the strange light that keeps Frank returning to work — the perpetual need for redemption and grace that prevents him from becoming cold to his job but makes his sanity fragile. In typical Scorsese-Schrader style, this is a raw, visceral, and very human search for grace in an unsparing urban hellscape.

Genre: Drama, Horror, Thriller

Actor: Afemo Omilami, Aida Turturro, Aleks Shaklin, Andy Davoli, Antone Pagán, Arthur J. Nascarella, Betty Miller, Brian Smyj, Catrina Ganey, Charis Michelsen, Cliff Curtis, Craig muMs Grant, David Zayas, Frank Ciornei, Fuschia!, Graciela Lecube, Jack O'Connell, James Hanlon, Jesse Malin, John Goodman, John Heffernan, Jon Abrahams, Joseph P. Reidy, Judy Reyes, Julyana Soelistyo, Larry Fessenden, Leonid Citer, Lia Yang, Marc Anthony, Mark Giordano, Martin Scorsese, Mary Beth Hurt, Mary Diveny, Marylouise Burke, Matthew Maher, Melissa Marsala, Michael Carbonaro, Michael Kenneth Williams, Michael Mulheren, Mtume Gant, Nestor Serrano, Nicolas Cage, Omar Scroggins, Patricia Arquette, Phyllis Somerville, Queen Latifah, Richard Spore, Sonja Sohn, Sylva Kelegian, Terry Serpico, Theo Kogan, Tom Cappadona, Tom Riis Farrell, Tom Sizemore, Ving Rhames

Director: Martin Scorsese

Rating: R

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, Arsinée Khanjian, Brooke Johnson, Bruce Greenwood, David Hemblen, Earl Pastko, Gabrielle Rose, Ian Holm, Marc Donato, Maury Chaykin, Mychael Danna, Peter Donaldson, Sarah Polley, Sarah Rosen Fruitman, Simon Baker, Stephanie Morgenstern, Tom McCamus

Director: Atom Egoyan

Rating: R