101 Best Challenging Movies On Itunes (Page 3)

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.

Find the best challenging movies to watch, from our mood category. Like everything on agoodmovietowatch, these challenging movies are highly-rated by both viewers and critics.

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

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

Danish writer-director Lars von Trier concludes his so-called Depression trilogy with the two parts of Nymphomaniac, an elaborate retelling of the life of a young woman (played by Stacy Martin and then, by Charlotte Gainsbourg) lived from one libidinous pleasure to another. The film's elaborate subplots have a life of their own and flashbacks often take center stage in Joe's auto-narration. Nymphomaniac I introduces the audience to adolescence and early adulthood, through disappointments, adultery, death drive, and extreme ambivalence. Joe's process of self-actualization seems contested and inspiring at the same time, and Gainsbourg is really given the screen time to shine; even more so than in Trier's previous psycho-social drama, Antichrist. Typically for the rich treasury of cultural references, Bach, Edgar Allan Poe, and Fibonacci play crucial parts in reconstructing the symbolic planes in Joe's story. Oh, and Part One opens with Rammstein's "Führe mich", which in itself is an perfectly valid reason to give it a go.

Genre: Drama

Actor: Ananya Berg, Anders Hove, Andreas Grötzinger, Charlotte Gainsbourg, Christian Slater, Christoph Jöde, Christoph Schechinger, Clayton Nemrow, Connie Nielsen, Cyron Melville, Hugo Speer, James Northcote, Jamie Bell, Jeff Burrell, Jens Albinus, Jesper Christensen, Jesse Inman, Mia Goth, Michael Pas, Nicolas Bro, Peter Gilbert Cotton, Saskia Reeves, Shia LaBeouf, Simon Böer, Sofie Kasten, Sophie Kennedy Clark, Stacy Martin, Stellan Skarsgård, Tomas Spencer, Uma Thurman, Willem Dafoe

Director: Lars von Trier

Rating: Not Rated, NR

I’m Not There is an unusual biopic in that it never refers to its subject, Bob Dylan, by name. Instead, Todd Haynes’ portrait of the singer mimics his constant reinvention by casting six separate actors to play as many reincarnations of the same soul. It’s an ingenious spin on a usually stale genre, one that liberates the film from the humdrum restrictions of a literal retelling of Dylan's life.

If there’s anyone who warrants such an inventive approach to biography, it’s Dylan, whose public and private personas are so numerous that it’s only by angling six different mirrors at him that Haynes can hope to catch some of his essence. Impressionistic editing toggles freely between these vignettes, each visually distinct: from the 11-year-old Woody Guthrie-obsessive (Marcus Carl Franklin) and the black-and-white Super 16mm-shot poet (Ben Whishaw) to the aging cowboy outlaw (Richard Gere), all by way of Christian Bale, Heath Ledger, and Cate Blanchett’s incarnations. To be sure, this is a somewhat challenging film, reflecting, in places, the enigmatic surrealism of Dylan’s lyrics and his refusal to be pinned down to one thing. But, as Blanchett’s embodiment says, “Mystery is a traditional fact,” and that’s no more true than of Dylan, making Haynes’ film a fascinatingly fitting spiritual biopic.

Genre: Drama, Music

Actor: Alison Folland, Andrew Shaver, Andrew Simms, Angela Galuppo, Arthur Holden, Ben Whishaw, Benz Antoine, Bill Croft, Bob Dylan, Brett Watson, Bruce Greenwood, Cate Blanchett, Catherine Colvey, Charlotte Gainsbourg, Christian Bale, Craig Thomas, Danny Blanco Hall, David Cross, David Gow, Dennis St John, Dominic James, Don Francks, Emmanuel Schwartz, Eric Newsome, Eugene Brotto, Fanny La Croix, Garth Gilker, Gordon Masten, Graham Cuthbertson, Greg Kramer, Heath Ledger, Holly Uloth, Ivan Freud, Jane Gilchrist, Jane Wheeler, Jason Cavalier, Jennifer Rae Westley, Jesse Todd, Jessica Kardos, Jim James, Jodie Resther, Joe Cobden, John Koensgen, Julianne Moore, Kathleen Fee, Kim Gordon, Kim Roberts, Kris Kristofferson, Kristen Hager, Kyle Gatehouse, Kyle Switzer, Larry Day, Leif Anderson, Leigh Ann Taylor, Lina Roessler, Lisa Bronwyn Moore, Lorne Brass, Maggie Castle, Marcus Carl Franklin, Marie-Julie Rivest, Mark Camacho, Matt Holland, Matthew Boylan, Matthew Harbour, Melantha Blackthorne, Michelle Williams, Nathalie Girard, Noel Burton, Patrick Costello, Paul Cagelet, Paul Johnston, Paul Spence, Pauline Little, Peter Friedman, Phyllis Gooden, Pier Paquette, Pierre Leblanc, Pierre-Alexandre Fortin, Richard Gere, Richard Jutras, Richard Robitaille, Richie Havens, Rob Burns, Roc LaFortune, Sharlene Royer, Shawn Baichoo, Steve Godin, Susan Glover, Terry Haig, Thiéry Dubé, Tim Post, Trevor Hayes, Tyrone Benskin, Vito DeFilippo, Wyatt Bowen, Yolonda Ross

Director: Todd Haynes

Rating: R

On the one hand, Godland is a film about nature’s unforgiving beauty. Like the photographs the priest Lucas (Elliott Crosset Hove) takes, these quietly superb scenes speak for themselves. The Earth moves in mysterious and harsh ways, and we are but mere specks, organic matter to be folded in and absorbed, in the grand scheme of things. It would’ve worked with just this message alone, but Godland also treads on political ground. Through Lucas, who is Danish, and his travel guide Ragnar (Ingvar Sigurdsson), who is Icelandic, we sense a palpable tension that electrifies the film with a colonial strain. There are layers to their deep aversion (and dependence) on one another, and director Hlynur Pálmason does well to pair this with imagery that is just complex, profound, and packed with meaning.

Genre: Drama

Actor: Elliott Crosset Hove, Ída Mekkín Hlynsdóttir, Ingvar E. Sigurðsson, Jacob Ulrik Lohmann, Vic Carmen Sonne, Waage Sandø

Director: Hlynur Palmason

In the movie Brazil, our hero Sam Lowery (Jonathan Pryce) lives in a dystopian world that relies on the cold productivity grind of machines. He’s in a constant battle between the high-level dominating powers that be and the low-level beatdown scums of society. Saving him from complete misery is a recurring dream he has of a beautiful woman. There, nothing else matters but love, which fills his draining soul and makes his life seem worthwhile. 

The way director Terry Gilliam handles a serious matter in such a comedic way is fantastic, and the amount of thought and effort he puts into creating every single bit of existence in this film is mind-boggling. With Brazil, he succeeds in establishing his own style, making a mark for himself in an age when plenty of auteurs compete for mere recognition.

Genre: Comedy, Drama, Science Fiction

Actor: Ann Way, Barbara Hicks, Bill Wallis, Bob Hoskins, Brian Miller, Bryan Pringle, Charles McKeown, David Gant, Derek Deadman, Derrick O'Connor, Don Henderson, Gorden Kaye, Harold Innocent, Howard Lew Lewis, Ian Holm, Ian Richardson, Jack Purvis, James Coyle, Jim Broadbent, John Flanagan, John Grillo, John Pierce Jones, Jonathan Pryce, Katherine Helmond, Kathryn Pogson, Kim Greist, Michael Palin, Myrtle Devenish, Nigel Planer, Oscar Quitak, Patrick Connor, Peter Vaughan, Ralph Nossek, Ray Cooper, Robert De Niro, Roger Ashton-Griffiths, Sheila Reid, Simon Jones, Terence Bayler, Terry Gilliam

Director: Terry Gilliam

Rating: R

This coming-of-age story based on the bestseller by the same name starts fun but veers towards darker territory. It's about a high-schooler who makes two older friends, played perfectly by Ezra Miller and Emma Watson. But as he gets closer to one of them, his anxieties and past trauma come to the surface. The impressive depth to which the makers of The Perks of Being a Wallflower were able to take it is what elevates it to greatness. It's the perfect mix between easy and challenging. If there is ever such a thing, it's this movie.

Genre: Comedy, Drama

Actor: Adam Hagenbuch, Brian Balzerini, Chelsea Zhang, Dihlon McManne, Dylan McDermott, Emily Marie Callaway, Emma Watson, Erin Wilhelmi, Ezra Miller, Joan Cusack, Joe Fishel, Johnny Simmons, Jordan Paley, Julia Garner, Kate Walsh, Landon Pigg, Leo Miles Farmerie, Logan Lerman, Mae Whitman, Mark McClain Wilson, Melanie Lynskey, Morgan Wolk, Nicholas Braun, Nina Dobrev, Patrick de Ledebur, Paul Rudd, Reece Thompson, Stacy Chbosky, Stephen Chbosky, Tom Savini, William L. Thomas, Zane Holtz

Director: Stephen Chbosky

Rating: PG-13

The Dardenne brothers deliver one of their characteristic tests of empathy with this social realist tale centered around an apparently irredeemable soul. Bruno (Jérémie Renier) and his girlfriend Sonia (Déborah François) are childish teenagers who have just welcomed their first baby, a boy named Jimmy. But the fact that he’s now a father and jointly responsible for a new life doesn’t seem to register with Bruno, a small-time criminal whose thoughts don’t extend beyond his next job and what he’ll buy with the takings.

Sickeningly, Jimmy’s birth gives the vacant-headed, impulsive Bruno an idea for a quick buck: he’ll use the black market to sell the baby to a family hoping to adopt. This awful act sets in motion a frantic set of events as Sonia’s horrified reaction signals to Bruno that he might have gone too far this time. Strikingly, though, we’re never sure if Bruno is experiencing a moment of genuine reflection — perhaps the first of his life — even up to the film’s dam-break of a final scene. The ghastliness of Bruno’s actions makes this a challenging watch, but the Dardenne brothers’ restraint and resolute refusal to moralize about their easily condemnable protagonist open it up to being a compelling reflective exercise on the limits of redemption.

Genre: Drama

Actor: Déborah François, Fabrizio Rongione, François Olivier, Jérémie Renier, Jérémie Segard, Mireille Bailly, Olivier Gourmet, Stéphane Bissot

Director: Jean-Pierre Dardenne, Luc Dardenne

This Oscar-nominated drama tells the story of the events leading up to the Srebrenica massacre, in which 8372 Bosnian Muslims were killed. It focuses on one U.N. worker who was caught between trying to protect her family, herself, and helping people in need.

The film is as horrific as it is relevant: up until the actual killing starts, people are constantly being assured that everything is under control and that there is no reason to panic. This gives an eerie feeling of resemblance to the tone many minorities in distress receive nowadays.

Still, Quo Vadis, Aida? stops at depicting any of the acts that were committed that day. Instead, it focuses on Aida’s unrelenting race against the clock to save whatever she can.

Genre: Drama, History, War

Actor: Alban Ukaj, Boris Isaković, Boris Ler, Dino Bajrović, Dražen Pavlović, Emina Muftić, Emir Hadžihafizbegović, Ermin Bravo, Ermin Sijamija, Izudin Bajrović, Jasna Đuričić, Job Raaijmakers, Joes Brauers, Johan Heldenbergh, Juda Goslinga, Micha Hulshof, Raymond Thiry, Reinout Bussemaker, Rijad Gvozden, Sanne den Hartogh, Sol Vinken, Teun Luijkx

Director: Jasmila Žbanić

Martin Scorsese’s Killers of the Flower Moon isn’t a whodunnit; in fact, it’s closer to a who-didn’t-do-it. We know from the very beginning who is responsible for committing the brutal serial murders of wealthy Osage Native Americans in 1920s Oklahoma that the film chronicles: pretty much every single one of their white neighbors, spearheaded by William Hale (a skin-crawling Robert De Niro). Scorsese, most often associated with mafia stories, stealthily suggests here that the most dangerous gang of all is the one into which all these perpetrators have been born. That’s an idea he investigates through the confused loyalties of Leonardo DiCaprio’s Ernest Burkhart, the Judas-like husband of Mollie (movie-stealer Lily Gladstone), an Osage woman who owns lucrative oil headrights that William wants to fatten his own pockets with. This searing epic — based on a harrowing chapter of real American history — is an unsparing and self-implicating look at complicity and greed in the eye, a monumental movie that cements its maker as one of the greatest to ever do it.

Genre: Crime, Drama, History

Actor: Barry Corbin, Ben Hall, Brendan Fraser, Cara Jade Myers, David Born, Elden Henson, Eric Parkinson, Gabriel Casdorph, Gary Basaraba, Gene Jones, J. C. MacKenzie, Jack White, James Healy Jr., Jason Isbell, Jay Paulson, Jesse Plemons, Jo Harvey Allen, Joe Chrest, Joey Oglesby, John Lithgow, Joshua Close, Justin France, Katherine Willis, Larry Fessenden, Larry Jack Dotson, Larry Sellers, Lee Eddy, Leonardo DiCaprio, Lily Gladstone, Louis Cancelmi, Marko Costanzo, Martin Scorsese, Michael Abbott Jr., Nathalie Standingcloud, Nathaniel Arcand, Nick W. Nicholson, Norma Jean, Pat Healy, Paul Woodiel, Pete Yorn, Robert De Niro, Scott Shepherd, Steve Eastin, Steve Routman, Steve Witting, Sturgill Simpson, Tantoo Cardinal, Tatanka Means, Ted Welch, Victor McCay, Vince Giordano, Wally Welch, Welker White, William Belleau

Director: Martin Scorsese

Rating: R

Wendy (Michelle Williams) is a drifter driving up to Alaska in hopes of finding work. When her car breaks down, she and her dog Lucy are stranded and forced to scrounge for food and repairs, hitting one roadblock after another on her path to an uncertain dream. This sympathetic and solemn look at poverty from director Kelly Reichardt serves as a reminder of how easy it is to fall through the fragile American safety net.   

Reichardt’s uncompromising approach paired with Williams’s restrained performance makes the experience authentic and intense, recalling the work of Ken Loach. This natural sharpness makes for an engrossing watch that builds in power until the emotional release of the film’s heartbreaking conclusion. 

Genre: Drama

Actor: Ayanna Berkshire, David Koppell, Deirdre OConnell, Gabe Nevins, Jeanine Jackson, John Breen, John Robinson, Larry Fessenden, M. Blash, Marilyn Faith Hickey, Michelle Williams, Wally Dalton, Will Oldham, Will Patton

Director: Kelly Reichardt

Rating: R

To plenty of countries around the globe, democracy has become so ubiquitous that we forget it’s relatively new, at least relative to the rest of human history. Bhutan is one of the last countries that became a democracy, and writer-director Pawo Choyning Dorji chose to depict a slice of how they made the shift in The Monk and the Gun. As Tashi sets out to obtain two weapons for his mentor, and Ron seeks a specific antique gun, Dorji presents slice-of-life moments of the beautiful Bhutan countryside, intercut with the subtle ways tradition still persists amidst modernity, and the funny ways change can clash with culture. It’s no wonder The Monk and the Gun was chosen as the Bhutanese entry for the Best International Feature at the 96th Academy Awards.

Genre: Drama

Actor: Choeying Jatsho, Deki Lhamo, Pema Zangmo Sherpa, Tandin Sonam, Tandin Wangchuk

Director: Pawo Choyning Dorji

This is the type of movie I completely fell in love with but cannot articulate exactly why. Maybe it's the mixture of beauty and pain portrayed, maybe it's the intricate sounds and beautiful imagery, maybe it's the story, maybe it's all of the above. A woman is hit with sudden disability after an accident and calls on an unlikely companion, a night club bouncer by the name of Ali. Together they explore her new predicament and its implications, while forming a special bond. This is a movie that will call upon your internal strength, while portraying how us humans can become strong together. Most of all it provides an immensely powerful, ultimately simple story that is both touching and will stay with you for a very long time. Directed by Jacques Audiard (A Prophet).

Genre: Drama, Romance

Actor: Armand Verdure, Bouli Lanners, Celine Sallette, Corinne Masiero, Fabien Baïardi, Françoise Michaud, Irina Coito, Jean-Michel Correia, Marion Cotillard, Matthias Schoenaerts, Mourad Frarema, Yannick Choirat

Director: Jacques Audiard

Rating: 15, R

It is hard to be unmoved by how Die Beautiful defies conventions and explores the essence of identity, acceptance, and resilience. Centered around the life of Trisha, a transgender woman with a passion for beauty pageants, the film takes us on a rollercoaster of emotions as we witness Trisha's life unfold, both in joyous moments and in the face of painful degradation and assault. The film seamlessly weaves together humor, tenderness, and raw vulnerability, delivered stunningly by its lead, Paolo Ballesteros. With other films such as Kalel, 15 and Bwakaw under his belt, director Jun Lana continues to meld reality with hope, injecting kindness and heart into much-needed queer stories.  

Genre: Comedy, Drama

Actor: Adrian Alandy, Albie Casiño, Cedrick Juan, Christian Bables, Eugene Domingo, Gladys Reyes, I.C. Mendoza, Iza Calzado, Jade Lopez, Joel Torre, Kokoy de Santos, Lou Veloso, Luis Alandy, Paolo Ballesteros

Director: Jun Lana, Jun Robles Lana

Rating: TV-14

Here’s a based-on-a-true-story courtroom drama that transcends the limits of its genre by virtue of an incisive and unexpectedly prescient script. Twenty years before 2016 sent us hurtling through the looking glass and into a post-truth era, the idea that you could deny the facts as you pleased teetered terrifyingly on the brink of legitimacy when author David Irving (a suitably odious Timothy Spall) brought a UK libel suit against Deborah Lipstadt (Rachel Weisz), an academic whom he claimed had defamed him for calling him exactly what he was: a Holocaust denier.

The case was complicated by the fact that, at the time, the UK placed the burden of proof on the defendant — in other words, Lipstadt’s hotshot legal team needed to prove that the Holocaust happened and that Irving had wilfully misrepresented evidence demonstrating this. Denial captures that terrifying farcicality and the defense’s cleverly counterintuitive strategy: not allowing Lipstadt or Holocaust survivors to speak. If that sounds unsatisfying — this is the rare courtroom drama with no grandstanding speech from the protagonist — that’s the point, something the film’s title cleverly alludes to. Perhaps unexpectedly, Denial’s relevance has ballooned since its release, a fact that might hobble its hopeful ending but that only makes the rest all the more powerful.

Genre: Drama, History

Actor: Abigail Cruttenden, Alex Jennings, Amanda Lawrence, Andrea Deck, Andrew Scott, Caren Pistorius, Daniel Cerqueira, Edward Franklin, Elliot Levey, Harriet Walter, Helen Bradbury, Hilton McRae, Ian Bartholomew, Jack Lowden, Jackie Clune, Jeremy Paxman, John Sessions, Lachele Carl, Laura Evelyn, Mark Gatiss, Max Befort, Mick Jackson, Nicholas Tennant, Nikki Amuka-Bird, Paul Bailey, Paul Hunter, Pip Carter, Rachel Weisz, Sally Messham, Sara Powell, Sean Power, Timothy Spall, Todd Boyce, Tom Clarke Hill, Tom Wilkinson, Will Attenborough, Ziggy Heath

Director: Mick Jackson

Rating: PG-13