473 Best Challenging Movies to Watch (Page 26)

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.

Admittedly, being released in theaters a month after Immaculate, The First Omen can almost be accused of being derivative, with similar protagonists, plots, and themes. However, unlike Immaculate, this film captures a bit of the 1970s horror style that was best seen in the original 1976 Omen film, with the paranoia, the investigations, the Eastman Kodak-inspired color grading, and the number of the devil now depicted in striking modern images and clearer digital definition. And, considering that the Roe decision was overturned two years ago, the idea of a forced virgin conception is a great way to reintroduce Gen Z to the horror franchise, as the prequel, and today’s women, now have to deal with religion and authority reducing women only into vessels. The First Omen is a timely adaptation that takes familiar horror tropes and executes them well.

Genre: Horror

Actor: Alessandra Fallucchi, Andrea Arcangeli, Anton Alexander, Bill Nighy, Charles Dance, Dobrila Stojnic, Dora Romano, Eva Ras, Ishtar Currie Wilson, James Swanton, María Caballero, Mario Opinato, Mia McGovern Zaini, Michelangelo Dalisi, Milena Božić, Miodrag Rakočević, Nell Tiger Free, Nicole Sorace, Rachel Hurd-Wood, Ralph Ineson, Sônia Braga, Sylvia Panacione, Tawfeek Barhom

Director: Arkasha Stevenson

Rating: R

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In many ways, the 1998 film The Truman Show forecasted how we’d interact with media today. Parasocial relationships are a thing, as is the feeling of entitlement we get when prying into other people’s lives. But before all that, Japanese TV producers were already testing the ethical limits of voyeurism through the reality show Denpa Shōnen, a social experiment of sorts that broadcasted how people would react in extreme situations. It was one of the first of its kind, and so The Contestant takes us through its novelty; smartly, it explains how and why a show so brutal was a massive hit. It tries to understand Japanese media and humor, not other it, while also sympathizing with Nasubi, who sits down for an enlightening interview. The documentary itself is revealing and disturbing—except for a confusing third act, in which it completely loses its critical air and tells a story of heroism that, while inspiring, feels detached from the rest of the film. What was the aftermath of all that cruelty? Did no one file a retroactive complaint? Is Japanese media still this intense and unwittingly cruel? These are things you’d expect the documentary would tackle by the end, but it confusingly doesn’t. Still, it’s an important and educational watch, one that hopefully serves as a cautionary tale against the ever-manipulative media and always-hungry viewer.

Genre: Documentary

Actor: Fred Armisen, Nasubi, Takehiro Hira, Toshio Tsuchiya

Director: Clair Titley

Rating: R

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Shot almost entirely in one take and on a tiny budget, and yet the central performance in this movie is still better than most big-budget dramas I’ve seen this year.

Two indigenous women, one upper-class and the other impoverished, meet on the day that the rich one gets an IUD and the other one, pregnant, finds herself kicked out of her home. They spend a few hours together: they talk, they take cabs, walk, etc; and you as a viewer, follow them throughout their intimate yet difficult moments.

If you like subtle movies that showcase how people live and interact with one another, beyond plot-obsessiveness, this is for you.

Genre: Drama

Actor: Aidan Dee, Anesha Bailey, Anthony Bolognese, Barbara Eve Harris, Charles Jarman, Charlie Hannah, Elle-Máijá Tailfeathers, Elle-Maija Tailfeathers, James Angus Cowan, Jay Cardinal Villeneuve, Kathleen Hepburn, Lissa Neptuno, Paul Jarrett, Sonny Surowiec, Tony Massil, Violet Nelson

Director: Elle-Máijá Tailfeathers, Elle-Maija Tailfeathers, Kathleen Hepburn

Rating: TV-MA

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Ballet has always captivated with its grace and poise, so of course it captivated cinema as well, with classics such as The Red Shoes and Black Swan centered on the dance, the culture, and of course, the drama. The juxtaposition of the ideal feminine form and the ugliness of competition, the sabotage, and the objectification are regular topics, but The American adds the national identity into its themes, tackling the anxieties of a young American in an academy that isn't friendly to outsiders. It's stunning. It gives justice to the journey of the real ballerina Joy Womack, portrayed excellently by Talia Ryder with breathtaking ease, and given dramatic flourish through the direction of James Napier Robertson. While it doesn’t quite surpass classic ballet films, Joika proves that real life ballet can be more emotional, more traumatic than any drama made about the dance.

Genre: Drama

Actor: Andrzej Andrzejewski, Andrzej Kłak, Borys Szyc, Charlotte Ubben, Diane Kruger, Edyta Torhan, Karolina Gruszka, Maciej Nawrocki, Marek Kasprzyk, Natalia Osipova, Natasha Alderslade, Oleg Ivenko, Robert Gulaczyk, Talia Ryder, Tomasz Kot

Director: James Napier

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The movie follows Martha (Vanessa Kirby), a young wife who loses her baby in a failed home birth. She tries her best to trudge through the aftermath of loss, but her coping attempts prove to be near impossible, not least because her husband Sean (Shia LaBeouf) and mother Liz (Ellen Burstyn) continually domineer every aspect of her life.

Pieces of a Woman is harrowing and heartbreaking, with the actors giving their all in this realistic and revealing drama. But it's Kirby's performance as the unraveled yet apathetic Martha that is the film's immediate standout, rightfully earning her a Best Actress nomination at the 2021 Academy Awards.

Genre: Drama

Actor: Alain Dahan, Benny Safdie, Domenic Di Rosa, Ellen Burstyn, Frank Schorpion, Gayle Garfinkle, Harry Standjofski, Harry Strandjofski, Iliza Shlesinger, Jimmie Fails, Leisa Reid, Molly Parker, Sarah Snook, Sean Tucker, Shia LaBeouf, Steven McCarthy, Tyrone Benskin, Vanessa Kirby, Vanessa Smythe

Director: Kornél Mundruczó, Kornél Mundruczó

Rating: R

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Where Palm Trees and Power Lines may stumble in its depiction of lower-middle class ennui among American teenagers (who are all made to seem not just bored, but boring), it more than makes up for in its delicate handling of power dynamics in its central relationship. To an outsider, Lea's decisions to let a stranger get so close to her are maddening, but co-writer and director Jamie Dack is careful to emphasize that the teenager ultimately isn't to blame. And Lily McInerny's entirely naturalistic performance communicates a fear of both missing out on life experiences and of being totally out of her depth.

Genre: Drama

Actor: Armani Jackson, Auden Thornton, Gretchen Mol, John Minch, Jonathan Tucker, Kenny Johnston, Lily McInerny, Michael Petrone, Timothy Taratchila, Yvette Tucker

Director: Jamie Dack

Rating: R

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There are horrors in the world that people have faced, and if they survive, they live with the trauma for a long, long time. But what happens when the perpetrator of that trauma has moved on? What happens when they resolve to be better, and pursue a different path? Our Father, the Devil is a psychological drama where an African refugee has to deal with seeing the warlord that once destroyed her entire village, but it unfolds in such a unique way, with the riveting Babetida Sadjo living a split life between her chef and caretaking career in the day, and being tormented by the past at night. It’s a fascinating portrait, one that we haven’t seen in a while, of a traumatized refugee granted the rare opportunity to exact retribution.

Genre: Drama, Mystery, Thriller

Actor: Babetida Sadjo, Franck Saurel, Jennifer Tchiakpe, Martine Amisse, Patrice Tepasso, Souleymane Sy Savane

Director: Ellie Foumbi

Rating: NR

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In certain heartbreaking instances, children are separated from their parents by the State, supposedly in hopes of finding them a better home. But for plenty of British and commonwealth orphans, the government process is, at worst, systematically designed to separate families to support the Kingdom’s colonies. While the film isn’t really focused on the details and the rationale behind the program, Oranges and Sunshine is much more concerned with the fact that it happened– that it has harmed hundreds of thousands of children for hundred years, and that it only took someone who cared enough to pay attention for things to actually change. It’s a decent depiction of Margaret Humphreys’ work, and it does a great job in promoting the Child Migrants Trust.

Genre: Drama, History

Actor: Aisling Loftus, Barbara Marten, Carolina Giammetta, Chrissie Page, David Wenham, Emily Watson, Geoff Morrell, Greg Stone, Harvey Scrimshaw, Hugo Weaving, Kate Rutter, Lorraine Ashbourne, Mandahla Rose, Marg Downey, Molly Windsor, Richard Dillane, Robert Purdy, Russell Dykstra, Stuart Wolfenden, Tanya Myers, Tara Morice

Director: Jim Loach

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Aspiring writer-director Vita of My First Film is insufferable. When she starts out making her first feature, she’s pleasantly surprised by the people who came to help her, but the repetition of the shoot, the scene not matching the idea in her head, which she tries to put into image and word, but can’t quite make the vision clear, the anxiety and pressure to be a professional filmmaker blinding her from the concerns of her cast and crew all combine to an inevitable failure of her first feature, which also happens to inspired by Vita’s actual life. Vita is insufferable, but writer-director Zia Anger manages to make her real in an eclectic meta multimedia patchwork that won’t work for everyone, but uniquely depicts an experience filmmakers, aspiring or otherwise, haven’t wanted to talk about.

Genre: Drama

Actor: Cole Doman, Devon Ross, Eamon Farren, Eléonore Hendricks, Jane Wickline, Joanna Fang, Odessa Young, Philip Ettinger, Sage Ftacek, Zia Anger

Director: Zia Anger

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In Tina Mabry’s first full length feature film Mississippi Damned she tells the story of three poor, Black adolescents as they advance into adulthood. The story is mostly centered on Kari Peterson, portrayed by Tessa Thompson, who has fallen witness and victim to violence/abuse since her childhood. As she navigates her trauma while facing poverty and familial issues, we begin to understand the inner machinations of Kari and those who have harmed her.

While Mississippi Damned isn’t particularly easy to digest, I consider it essential. As unflinchingly brutal as this film is, it taught me a lot about trauma and how to navigate my own. With performances as powerful as these, it’s impossible to forget this film.

Genre: Drama

Actor: Adam Clark, Cynthia Addai-Robinson, D.B. Woodside, Malcolm David Kelley, Malcolm Goodwin, Michael Hyatt, Simbi Khali, Tessa Thompson

Director: Tina Mabry

Rating: TV-MA

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