33 Best Challenging Movies On Amazon Prime

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

Not one but two Oscars as well as a Golden Globe are among this movie’s never-ending list of accolades. It was the first Iranian film ever to get an Oscar and the first non-English film ever nominated for Best Screenplay. Originally titled The Separation of Nader from Simin in Persian, it homes in on the dissolving relationship of a middle-class couple from Teheran – and the unintended consequences of tragic events.

However, this film is so intense, well-acted, and well-written, it defies categorization. To be sure, the movie does offer a painful look at a deteriorating marriage. It’s also timely, dealing with the politics of theocracy, economic underdevelopment, and social alienation. It presents tense moral dilemmas without pointing a finger. If you’re curious to learn about the humans of Iran and, by cultural extension, the humans of the Middle East beyond the scope of global politics, A Separation is also for you.

But please don’t call it world cinema, because this is no Slumdog Millionaire. Above all, it is a searing portrayal of human conflict, relationships, and morals. It is an almost perfect depiction of how many bad people are simply good people running out of options.

Genre: Drama

Actor: Ali-Asghar Shahbazi, Babak Karimi, Bahareh Riahi, Kimia Hosseini, Leila Hatami, Merila Zare'i, Payman Maadi, Peyman Maadi, Peyman Moaadi, Sahabanu Zolghadr, Sare Bayat, Sareh Bayat, Sarina Farhadi, Shahab Hosseini, Shirin Yazdanbakhsh

Director: Asghar Farhadi

Rating: PG-13

Genre: Comedy, Drama

Actor: Absa Diatou Toure, Alba Gaïa Kraghede Bellugi, Alba Gaïa Bellugi, Anne Le Ny, Antoine Laurent, Audrey Fleurot, Benjamin Baroche, Camila Samara, Caroline Bourg, Christian Ameri, Clotilde Mollet, Cyril Mendy, Dominique Daguier, Dorothée Brière, Elliot Latil, Émilie Caen, François Bureloup, François Caron, François Cluzet, Grégoire Oestermann, Hedi Bouchenafa, Ian Fenelon, Jean-François Cayrey, Jérôme Pauwels, Joséphine de Meaux, Joséphine de Meaux, Marie-Laure Descoureaux, Michel Winogradoff, Nicky Marbot, Omar Sy, Philippe Pozzo di Borgo, Pierre-Laurent Barneron, Renaud Barse, Salimata Kamate, Sylvain Lazard, Thomas Solivérès, Yun-Ping He

Director: Eric Toledano, Olivier Nakache

Rating: R

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, Domenico Toledo, Ezra Marder, Hillary Baack, Jamie Ghazarian, Lauren Ridloff, Mathieu Amalric, Michael Tow, Olivia Cooke, Paul Raci, Rena Maliszewski, Riz Ahmed, Sean Powell, Shaheem Sanchez, Tom Kemp, William Xifaras

Director: Darius Marder

Rating: R

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

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: Al Vandecruys, 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, Clarice Byrne, Craig Thomas, Daniel Richard Giverin, 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, Hélèna Laliberté, Holly Uloth, Ivan Freud, Jane Gilchrist, Jane Wheeler, Jason Cavalier, Jean-Loup Yale, Jennifer Rae Westley, Jesse Todd, Jessica Kardos, Jim James, Jodie Resther, Joe Cobden, Joey Burns, John Koensgen, Julianne Moore, Kathleen Fee, Kathryn Kostlivy, 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, Max Walker, Melantha Blackthorne, Michelle Williams, Mike Caruso, 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, Shaun Balbar, 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

As an adaptation of a story written to commemorate the Louvre’s comics-focused exhibit, Rohan at the Louvre expands the short story into a riveting, nearly two-hour supernatural mystery film that contemplates Japanese art in context with the world. The original story is a spin-off of the popular manga Jojo’s Bizarre Adventure, so this film adaptation may shock fans expecting the same plot points and the vibrant, colorful style of the manga. However, the shadow-heavy cinematography, alongside Issey Takahashi’s performance, casts the eeriness needed to make this story work on film. It’s a change that fits a story all about art as a depiction of pain and desire, severing the self from the past, and escapism through stories.

Genre: Action, Adventure, Drama, Mystery

Actor: Fumino Kimura, Issey Takahashi, Katia Tchenko, Kayoko Shiraishi, Kazutaka Watanabe, Kei Kagaya, Kento Nagao, Kou Maehara, Léa Bonneau, Makoto Nakamura, Marie Iitoyo, Masanobu Ando, Minami, Robin Barde, Ryo Ikeda, Ryosuke Otani, Tomoya Masuda

Director: Kazutaka Watanabe

Genre: Drama, Science Fiction, Thriller

Actor: Chete Lera, Eduardo Noriega, Fele Martínez, Gérard Barray, Ion Gabella, Jorge de Juan, Joserra Cadiñanos, Miguel Palenzuela, Najwa Nimri, Pedro Miguel Martínez, Penélope Cruz, Pepe Navarro, Tristán Ulloa, Walter Prieto

Director: Alejandro Amenábar

Rating: R

Alejandro González Iñárritu's cleverly layered directorial feature film debut follows three persons whose lives are connected by a car crash in Mexico City. It directly involves two of them: a young man who enters the world of dogfighting to earn enough to elope with his sister-in-law, and a supermodel whose life is changed for the worse after she is fatally injured. The third segment of the film centers on a mysterious homeless man on the street who witnesses the crash.

The title, Amores Perros, refers to the characters’ love of dogs as well as love being a source of misery, and it’s a hint of the chaotic, unforeseen circumstances they each face. Iñárritu’s film shows his brilliance in direction. Despite the film being an early work, his ingenuity shines through and the compelling performances propel all three stories to gritty heights.

Cut-throat editing, handheld cinematography, and Guillermo Arriaga’s intricate screenplay flesh out each character. The viewers are pushed to the edge of their seats as we navigate the gripping miseries of life along with the rest of the cast. The tightly woven film is a painful must-watch, a brutal and uncompromising look at despair and animalistic aggression among humans that is also mirrored in the cruelty their dogs suffer.

Genre: Drama, Thriller

Actor: Adriana Barraza, Alvaro Guerrero, Dagoberto Gama, Dunia Saldívar, Emilio Echevarría, Gael García Bernal, Gerardo Campbell, Goya Toledo, Gustavo Muñoz, Gustavo Sánchez Parra, Humberto Busto, Jorge Salinas, José Sefami, Laura Almela, Lourdes Echevarría, Marco Perez, Mauricio Martínez, Patricio Castillo, Ricardo Dalmacci, Roberto Medina, Rodrigo Murray, Rodrigo Ostap, Rosa María Bianchi, Vanessa Bauche

Director: Alejandro González Iñárritu

Rating: R

Earnest, beautiful, and tender, Luca Guadagnino's Bones and All is many things: a road trip movie that sweeps the midwest deserts of 1980s America; a coming-of-age story that brings together two outsiders into an understanding world of their own; and a cannibal film that is unflinchingly flesh deep in its depiction of the practice. Bizarrely, these seemingly disparate elements work harmoniously to create a film that you won't soon forget, not least because of its rawness. 

As the aforementioned outsiders, Maren and Lee (Taylor Russell and Timothée Chalamet, respectively) are bewitching—individually sure but especially when they're together. They have a bond that is quite difficult to replicate onscreen, charged as it is with so much chemistry and warmth. The background players also bring their a-game when called for, especially Mark Rylance as the disturbing stalker Sully, Michael Stuhlbarg as the creepy but good-willed Jake, and Chloë Sevigny as Maren's stark mad mother. 

It's worth repeating that this movie goes all in on the gore, so steer clear if you don't have the heart for these sorts of things. But if you do, the viewing experience is rewarding. Bones and All is as romantic as they get, and rather than bury its message, the many layers on top of its core serve as a meaningful puzzle to unpack and unravel long after the credits roll.

Genre: Drama, Horror, Romance

Actor: Andre Holland, Anna Cobb, Brady Gentry, Chloe Sevigny, Christine Dye, David Gordon Green, Hannah Barlow, Jake Horowitz, Jenny McManus, Jessica Harper, Johanna McGinley, Madeleine Hall, Marcia Dangerfield, Mark Rylance, Michael Stuhlbarg, Sean Bridgers, Taylor Russell, Timothée Chalamet, Tom O'Brien

Director: Luca Guadagnino

Rating: R