59 Best Challenging Movies On Itunes Australia

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.

Understated in budget but lavished with praise, this semi-autobiographical drama by Daniel Destin Cretton flings its audience into the chaotic lives and personal crises of at-risk youths and the passionate social workers that aid them. In his first feature film, the young director draws the viewers into the storm of events and the emotional ups-and-downs of social work in America, going from uplifting to depressing and back – and every emotion in-between.

Set in the real-life and eponymous group home Short Term 12, devoted but troubled foster-care worker Grace is played by Brie Larson, whose shining performance in her first leading role was lauded by critics. Fans will also recognize the supporting actors Lakeith Stanfield and Rami Malek, who broke out in this movie. Short Term 12 is now considered one of the most important movies of 2013 – some say of the decade – owing to its immaculate writing, intimate camerawork, and gripping performances.

Genre: Drama

Actor: Alex Calloway, Angelina Assereto, Brie Larson, Diana Maria Riva, Frantz Turner, Harold Cannon, Joel P. West, John Gallagher Jr., Kaitlyn Dever, Keith Stanfield, Kevin Hernandez, Lakeith Stanfield, Lydia Du Veaux, Melora Walters, Michelle Nordahl, Mohammad Shiravi, Rami Malek, Silvia Curiel, Stephanie Beatriz

Director: Destin Cretton, Destin Daniel Cretton

Rating: R

Legend has it that director Derek Cianfrance had the co-stars and co-executive producers Michelle Williams and Ryan Gosling live together in the same house for a month in preparation of their roles. The fictional couple they play in Blue Valentine lived in the same house. True or not, this created the harsh proximity, intensity, and claustrophobia that is a hallmark of this production. Blue Valentine brings us painfully close to the couple's attraction as well as their agony.

In this way, Blue Valentine is a heart-breaking examination of the decaying shell of a once-bright marriage. As sad as it is sexy, it mixes intense flashbacks of past desire with the grim reality of married life's monotony. It boasts an electrifying performance from Michelle Williams and Ryan Gosling, who seamlessly combine tenderness and lust, rage and sadness. This is a guaranteed tear-jerker, so make sure you've brought your Kleenexes!

Genre: Drama, Romance

Actor: Alan Malkin, Ashley Gurnari, Barbara Troy, Ben Shenkman, Carey Westbrook, Enid Graham, Faith Wladyka, Ian Bonner, James Benatti, Jen Jones, John Doman, Joseph Basile, Mark Benginia, Marshall Johnson, Maryann Plunkett, Michelle Williams, Mike Vogel, Robert Russell, Ryan Gosling, Tamara Torres

Director: Derek Cianfrance

Rating: R

A follow-up/companion piece to the award-winning The Act of Killing, The Look of Silence is another compelling documentary from Director Joshua Oppenheimer. Both films aim attention at the Indonesian Genocide of 1965-66, when the military government systematically purged up to one million communists. While the first film's focus was on the culprits and on providing facts, the second one lets us meet the victims. One victim in particular: a soft-spoken optician named Adi Rukun, who meets with various members of the death squad who murdered his elder brother Ramli, under the guise of giving them an eye test. As he questions them about the killings, the murderers, again, show little remorse and eagerly provide the lurid details to the many executions. It's a stunning and provocative look at the legacy of historical mass killings, along with the insidious propaganda that provokes them, and continues to justify them to younger generations. A testament to the power of cinema to remember the forgotten.

Genre: Documentary, History

Actor: Adi Rukun, Amir Hasan, Inong, Joshua Oppenheimer, M.Y. Basrun

Director: Joshua Oppenheimer

Rating: PG-13

Ahmed plays Ruben Stone, a heavy metal drummer, who plays in a band and lives in a tour bus with his girlfriend Lou (Olivia Cooke). Quickly after meeting the couple, we witness the touring musician drastically losing his hearing. As recovering addicts with little financial means, they soon run out of options. Lou desperately wants to prevent Ruben's relapse into addiction and so she helps him retreat to a deaf community group home, run by the illustrious Joe, a truly amazing character played by the equally amazing Paul Raci, himself the hearing son of deaf parents. There is something deeper going on though: the question of what disability is, and how, despite how it drastically changes Ruben's life, it might not be his biggest problem. In addition to the stellar acting and delicate writing, we experience his condition through the incredible sound design used by director Darius Marder, complete with muffled conversations, garbled noises, and piercing silence. This is a movie to be taken in completely. Above all, it's about Riz Ahmed's performance. He learned to play drums, sign language, and studied deafness ahead of the shooting, and he does not strike a wrong note.

Genre: Drama, Music

Actor: Alan Resnic, Bill Thorpe, Chelsea Lee, Chris Perfetti, Ezra Marder, Hillary Baack, Jamie Ghazarian, Lauren Ridloff, Mathieu Amalric, Michael Tow, Olivia Cooke, Paul Raci, Rena Maliszewski, Riz Ahmed, Tom Kemp, William Xifaras

Director: Darius Marder

Rating: R

Nothing about Saint Omer is easy. A female Senegalese migrant (Guslagie Malanga) is put to trial for committing infanticide, but throughout the film, it becomes clear how much of a victim she is too, of an uncaring and deeply prejudiced society. “What drove her to madness?” Her attorney asks at one point. We’re not sure. We're not necessarily asked to side with her, nor answer the many hard-hitting questions brought up in the film, but we sit with the uneasiness of it all and, in that silence, confront our ideas about motherhood, womanhood, personhood. 

This confusion is what makes the film so compelling. Despite the court’s best efforts, Laurence isn’t meant to be understood. She’s meant to be an example of the ever-ambiguous, forever-complicated, always-hurt person. It’s human nature after all to be this complex and messed up. The film shows us that the best that we can do in situations like this is to listen, understand, and as our protagonist Rama (Kayije Kagame) does, make peace with the noise. 

Genre: Crime, Drama

Actor: Aurelia Petit, Guslagie Malanda, Kayije Kagame, Louise Lemoine Torrès, Salimata Kamate, Valérie Dréville, Xavier Maly

Director: Alice Diop

In a world where mortality has been overcome, people watch in awe as the as the 118-year-old Nemo Nobody, the last mortal on Earth, nears his end. He is interviewed about his life, recounting it at three points in time: as a 9-year-old after his parents divorced, when he first fell in love at 15, and as an adult at 34. The three stories seemingly contradict each other. Utilizing non-linear cinematography, Belgian director Jaco Van Dormael presents each of these branching pathways as a version of what could have been. The result is a complex, entangled narrative. That and the movie's ensemble cast, featuring Jared Leto, Sarah Polley, and Diane Kruger, have turned Mr. Nobody into a cult classic. The soundtrack, featuring several of the beautifully restrained music by Eric Satie, is also considered a masterpiece. While it is surely not for everybody, this is trippy, intimate, and existential sci-fi at its best.

Genre: Drama, Fantasy, Mystery, Romance, Science Fiction

Actor: Aaron Landt, Alice van Dormael, Allan Corduner, Andrew Simms, Audrey Giacomini, Ben Mansfield, Carlo Mestroni, Catherine Demaiffe, Christelle Cornil, Christophe Beaucarne, Clare Stone, Daniel Brochu, Daniel Mays, David Kennedy, David Schaal, Diane Kruger, Dominique Warnier, Harold Manning, Harry Cleven, Hugo Harold-Harrison, Jan Hammenecker, Jared Leto, Jenna Wheeler-Hughes, John Churchill, Juliette Van Dormael, Juno Temple, Laura Brumagne, Laurent Capelluto, Leni Parker, Linh Dan Pham, Lola Pauwels, Manfred Andrae, Marc Zinga, Marie-Ève Beauregard, Martin Swabey, Natasha Little, Nicholas Beveney, Olivier Bony, Pascal Duquenne, Philippe Godeau, Philippe Lévy, Pierre Chaves, Rhys Ifans, Roline Skehan, Sandrine Laroche, Sarah Gravel, Sarah Polley, Serge Larivière, Stéphane Taillasson, Sylvie Olivé, Tedd Dillon, Thomas Byrne, Toby Regbo, Vincent Dupont, Virginie Bordes, Vito DeFilippo

Director: Jaco Van Dormael

Rating: R

Winning him Best Director at the Academy Awards, Kenneth Lonergan's drama Manchester By the Sea is a delicate and profound study of loss and grief—and a true triumph. Its focus on characters, well-paced unfolding as well as world-class acting are only equal to the very best of European dramas. This type of quiet exploration of the possibility that grief cannot be overcome has rarely been successful in American cinema, if ever. The last best attempt was probably You Can Count on Me. Originally a playwright, this is Lonergan's third film and Manchester by the Sea is where he unveils his full potential. It follows a depressed handyman, Lee Chandler (Casey Affleck), who leads a quiet but angry life. After his brother dies, he returns to his hometown only to discover that he is the only left to take care of his teenage nephew. There, he is confronted with his past and the blue-collar community from which he was raised. Co-produced by Matt Damon, it grossed around $80 million on a budget of $8.5 million. One of the most noted films of 2016.

Genre: Drama

Actor: Allyn Burrows, Anna Baryshnikov, Anthony Estrella, Ben Hanson, Ben O'Brien, Brian A. White, C.J. Wilson, Carolyn Pickman, Casey Affleck, Christian J. Mallen, Danae Nason, Ellie Teves, Erica McDermott, Frank Garvin, Gretchen Mol, Heather Burns, Ivy O'Brien, Jackson Damon, Jami Tennille, Joe Stapleton, Josh Hamilton, Kara Hayward, Kenneth Lonergan, Kt Baldassaro, Kyle Chandler, Lewis D. Wheeler, Liam McNeill, Lucas Hedges, Matthew Broderick, Michelle Williams, Missy Yager, Nellie Lonergan, Oscar Wahlberg, Quincy Tyler Bernstine, Richard Donelly, Robert Sella, Ruibo Qian, Shawn Fitzgibbon, Stephen Henderson, Stephen McKinley Henderson, Susan Pourfar, Tate Donovan, Tom Kemp, Wendy Overly, William Bornkessel, Zain Ullah

Director: Kenneth Lonergan

Rating: R

, 2011

It might seem like a no-brainer that trying to make a comedy movie featuring a character with cancer is not a great idea. And while there may be a good share of failed attempts in that category, 50/50 is not one of them. And then it might come as a surprise that this subtle attempt at cancer comedy comes courtesy of Superbad creators Seth Rogen and Evan Goldberg. It also stars indie cutie Joseph Gordon-Levitt as the young and fit Adam Lerner, who works as a writer for public radio before learning that he has malignant tumors all along his spine. Between his overbearing mum (Anjelica Huston), slightly obnoxious but good-hearted bestie (Seth Rogen), self-help groups, and his therapist (played by Anna Kendrick), he struggles to find a way of acquiescing to his 50/50 chance of survival. Similarly, 50/50 strikes a delicate balance between the bromance gags, the date-movie elements, and the grave subject matter at its heart. It manages to mine humor, pathos, and simple honesty from a dark situation, and is not afraid to “go there”. The result is truly compassionate comedy.

Genre: Comedy, Drama

Actor: Adrian Glynn McMorran, Amitai Marmorstein, Andrea Brooks, Andrew Airlie, Anjelica Huston, Anna Kendrick, Beatrice King, Brent Sheppard, Bryce Dallas Howard, Cameron K. Smith, Chilton Crane, Christopher De-Schuster, D.C. Douglas, Daniel Bacon, Donna Yamamoto, Jason Vaisvila, Jessica Parker Kennedy, Jonathan Levine, Joseph Gordon-Levitt, Laura Bertram, Lauren Miller, Luisa D'Oliveira, Marie Avgeropoulos, Matt Frewer, Matty Finochio, P. Lynn Johnson, Peter Kelamis, Philip Baker Hall, Sarah Smyth, Serge Houde, Seth Rogen, Stephanie Belding, Stephen Colbert, Sugar Lyn Beard, Tom MacNeill, Veena Sood, Will Reiser, William 'Big Sleeps' Stewart, Yee Jee Tso

Director: Jonathan Levine

Rating: R

Nebraska is a poem distilled into a film. Peter Travers from Rolling Stone says "is it a comedy or a drama? Both at the same time, as life itself." Everything about it is perfect: the acting, the photography, the story. In case that's not enough and you need to know the plot to get convinced, I'll tell you that it's a road movie about a senile old man and his son. If you still want more information, you can Google it, but come on! You'll just be wasting time that would be better spent on watching this masterpiece.

Genre: Adventure, Drama

Actor: Angela McEwan, Anthony G. Schmidt, Bob Nelson, Bob Odenkirk, Bruce Dern, Devin Ratray, Franklin Dennis Jones, June Squibb, Mary Louise Wilson, Missy Doty, Rance Howard, Stacy Keach, Tim Driscoll, Will Forte

Director: Alexander Payne

Rating: R

In Playground, we follow seven-year-old Nora as she navigates friends and school. Through her eyes (and often on her eye level), we witness her and her brother trying and often failing to fit in.

The film is an unfiltered account of their formative years, and possibly a reflection of our own. Commercials and kid-friendly media would have us believe that childhood is simple and pure, but the truth is it isn’t exempt from the major pitfalls of humanity. Children will mimic whatever they see, reasonable or otherwise, and the resulting order won’t always be ideal. Case in point: in the schoolyard, free of adult supervision, Nora and her peers push and tease and harass one another. 

It’s painful but relatable, a microcosm of our own complicated world, and though the film doesn’t shy away from the cruelties of bullying, it’s also filled with moments of empathy and warmth.

Genre: Drama

Actor: Anne-Pascale Clairembourg, Karim Leklou, Laura Verlinden, Sandrine Blancke, Simon Caudry

Director: Laura Wandel

The film stars Jake Gyllenhaal as Lou Bloom, an impromptu freelance videographer who begins covering the crime world in LA for a local TV station. Almost as dark as a mystery can get, it is disturbing, and plays out as a combination of "Drive" and "The Network". The film is visually stunning as well as immensely suspenseful. It then becomes almost impossible to look away, even when you're the most horrified by just how far Bloom is willing to go to reach success. Gyllenhaal's performance is widely compared to that of Robert De Niro in Taxi Driver, which should give you an idea of its caliber.

Genre: Crime, Drama, Mystery, Thriller

Actor: Alex Ortiz, Ann Cusack, Bill Blair, Bill Paxton, Bill Seward, Carolyn Gilroy, Chris Wolfe, Christina De Leon, Dale Shane, Dan Gilroy, Dig Wayne, Eric Lange, Holly Hannula, Jake Gyllenhaal, James Huang, Jamie McShane, Jonny Coyne, Kathleen York, Kent Shocknek, Kevin Dunigan, Kevin Rahm, Kiff VandenHeuvel, Leah Fredkin, Marco Rodriguez, Merritt Bailey, Michael Hyatt, Michael Papajohn, Myra Turley, Pat Harvey, Price Carson, Rene Russo, Rick Chambers, Rick Garcia, Riz Ahmed, Sharon Tay, Stephanie D'Abruzzo, Viviana Chavez

Director: Dan Gilroy

Rating: R

It's heartbreaking to realize that Happening, a film set in 1960s France tracking a young woman's journey to dangerously and desperately terminating her pregnancy, is still very much relevant and relatable to this day. Around the world, abortion is still inaccessible, if not completely illegal, and women still struggle to lay full claim to their bodies. A lot of girls grow up with pregnancy statistics meant to instill fear, but Happening brings all that to brilliant life in intimate and unrestrained detail. The fears and wants of our protagonist Anne (played precisely by Anamaria Vartolomei) are palpable throughout. Nothing is held back in this film, and if you find yourself sick in parts, then it has achieved its goal of realistically conveying what it's like to stay alive in a society that fails to recognize your needs. 

 

Genre: Drama, History

Actor: Alice de Lencquesaing, Anamaria Vartolomei, Anna Mouglalis, Cyril Metzger, Édouard Sulpice, Fabrizio Rongione, Francois Loriquet, Julien Frison, Kacey Mottet Klein, Leïla Muse, Louise Chevillotte, Louise Orry-Diquéro, Luàna Bajrami, Pio Marmaï, Sandrine Bonnaire

Director: Audrey Diwan

Rating: R

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

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