6 Best Challenging Movies On Max (HBO Max)

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.

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

Sometimes you can just tell a movie means way too much to the people who made it. That makes me want to watch it more than once, which is what I wanted to do with The Tale. But while I think it's such an amazing movie and everyone should watch it, I don't think I can stomach a second watch.. It is based on the director/writer Jennifer Fox's own story - recounting her first sexual experience at a very young age. It's about the stories we tell ourselves to deal with trauma, and in that sense, and with utmost honesty, it invites grief and closure for similar experiences. A powerful movie led by a powerful performance by Laura Dern as Jennifer.

Genre: Drama, Mystery, TV Movie

Actor: Chelsea Alden, Common, Daniel Berson, Deana Deatherage, Elizabeth Debicki, Ellen Burstyn, Emily Sandifer, Frances Conroy, Grant James, Gretchen Koerner, Isabella Amara, Isabelle Nélisse, Jaqueline Fleming, Jason Ritter, Jenson Cheng, Jered Meeks, Jessica Sarah Flaum, Jodi Long, John Heard, Juli Erickson, Katie Fairbanks, Laura Allen, Laura Dern, Lonnie Rashid Lynn Jr., Madara Jayasena, Madison David, Matthew Rauch, Mobin Khan, Noah Lomax, Paul Riley Fox, Pixie Hankins, Rebecca Chulew, Ricki Bhullar, Russell Bradley Fenton, Scott Takeda, Tarek Bishara, Thom Bishops, Tina Parker, Vincent Washington

Director: Jennifer Fox

Rating: Not Rated

Twisted yet deep. Sad yet interesting. Slow yet exhilarating. A Ghost Story is an incredible artistic achievement. With hardly any dialog, and breathtakingly long takes in its first half, it manages to bring you in its own creepy world and not let go until you feel completely lonely. Starring Rooney Mara and Casey Affleck as a loving couple who are hit with a horrible tragedy, the beginning is slow, and it's not a plot driven movie, but if you give it a chance it will blow your mind.

Genre: Drama, Fantasy, Romance

Actor: Augustine Frizzell, Barlow Jacobs, Brandi Price, Brea Grant, Carlos Bermudez, Casey Affleck, Chris Gardner, David Lowery, David Pink, Giovannie Cruz, Grover Coulson, Jonny Mars, Kenneisha Thompson, Kesha, Kesha Rose Sebert, Liz Cardenas, Liz Cardenas Franke, Liz Franke, McColm Cephas Jr., Nikita Patel, Rob Zabrecky, Rooney Mara, Sonia Acevedo, Will Oldham, Yasmina Gutierrez

Director: David Lowery

Rating: R

You may have heard about this 2019 critic-favorite from clips like this one of a kid running to flee the movie theater during a screening. “little billy ran the f**k out the door”, the caption reads.

You will want to do the same. Recovering from losing her sister and her parents in a single incident, a young girl goes on a trip to Sweden to observe a ritual within a bizarre commune that occurs every 90 years. This cult’s idea of death and their traditions intersect with the girl’s grief to create unthinkable monstrosities.

Note: while some readers praise the movie for its depiction of anxiety, I highly recommend against watching Midsommar if you suffer from panic attacks.

Genre: Drama, Horror, Mystery

Actor: Agnes Westerlund Rase, Anders Back, Anders Beckman, Anki Larsson, Anna Åström, Anna Berentzen, Archie Madekwe, Austin R. Grant, Björn Andrésen, Ellora Torchia, Florence Pugh, Frans Cavallin Rosengarten, Gunnel Fred, Hampus Hallberg, Henrik Norlen, Isabelle Grill, Jack Reynor, Julia Ragnarsson, Katarina Weidhagen, Klaudia Csányi, Lars Väringer, Lennart R. Svensson, Levente Puczkó-Smith, Liv Mjönes, Louise Peterhoff, Mats Blomgren, Mihály Kaszás, Rebecka Johnston, Tove Skeidsvoll, Vilhelm Blomgren, Vilmos Kolba, Will Poulter, William Jackson Harper, Zsolt Bojári

Director: Ari Aster

Rating: R

For the longest time, American media coverage was skewed to justify the presence of US forces in Arab states. Control Room unveils that bias by following Al Jazeera at the start of the Iraq War in 2003. One of the biggest Arab media outlets at the time, Al Jazeera dared to cover both sides of the war, but by doing so put a target on its back. It was vilified by both the US government, which called it an Osama mouthpiece and the Arab world, which called it a Bush ally. 

Control Room shows the difficulty (if not sheer impossibility) of achieving journalistic balance, objectivity, and integrity. Through interviews with Al Jazeera reporters and US military officers, we witness how lines are blurred, loyalties are tested, and purpose is shifted in a state of war. A seminal work on media bias and press control, Control Room is vital and enlightening, a must-watch to understand the inner workings of the fourth estate. 

Genre: Documentary, War

Actor: Donald Rumsfeld, George W. Bush, Josh Rushing

Director: Jehane Noujaim

With its wildly different shifts between the film’s chapters, Bad Education feels like it doesn’t know what to do with itself, like plenty of newly graduated teenagers. The first chapter holds such visceral revulsion that it first feels like it would be a serious cautionary tale, commenting on how, without guidance, teenagers will led each other astray. However, its next chapter takes a more comedic route as the kids try to escape from gangsters and the police. While director Kai Ko reveals an excellent sense of direction and imagery, his style feels like it’s been wasted on ill-thought intentions and a poorly written script. Bad Education at least has stunning visuals and a short runtime to get through it all.

Genre: Crime, Drama, Mystery, Thriller

Actor: Berant Zhu, Cheng Chih-wei, Edison Song, Hong Yu Hong, Huang Hsin-Yao, Kai Ko, Kent Tsai, Kurt Hsiao, Leon Dai, McFly Wu, Ning Chang, Tzu-Chiang Wang

Director: Kai Ko