319 Best Depressing Movies to Watch (Page 4)

The story of the Von Erich family is excruciatingly sad, but Iron Claw doesn’t dive right into the tragedy. Instead, it takes care to paint a picture of a close-knit family that’s filled with just as much warmth, jealousy, affection, and resentment as the next bunch. Durkin masterfully draws you into their circle so that everything that happens next is sure to cut deep. The choreography, chemistry, color—everything is carefully and beautifully set up, but the casting is what stands out the most. This wouldn’t have worked as well if it weren’t for the inspired move to pair Zac Efron, Jeremy Allen White, Harris Dickinson, and Stanley Simons as brothers and partners. On the internet, people have been dubbing The Iron Claw as “Little Women and The Virgin Suicides for men” and it’s not hard to see why. Apart from the sibling bond over glory and growing pains, all these films are also powerful explorations of gender. Iron Claw is a vicious takedown of toxic masculinity, while also being a searing family drama and an incredible showcase for Efron and company.

Genre: Drama, History

Actor: Aaron Dean Eisenberg, Brett Beoubay, Brian Hite, Cassidy O'Reilly, Cazzey Louis Cereghino, Chad Governale, Chavo Guerrero Jr., Chelsea Edmundson, Christina Michelle Williams, Ernest Marsh, Garrett Hammond, Harris Dickinson, Holt McCallany, Jeremy Allen White, Jim Gleason, Jullian Dulce Vida, Kevin Anton, Kristina Kingston, Lily James, Maura Tierney, Maxwell Friedman, Maxwell Tyler Friedman, Michael Harney, Michael Papajohn, Mike Dell, Ryan Nemeth, Scott Innes, Stanley Simons, Timothy Hinrichs, Zac Efron

Director: Sean Durkin

Rating: R

You've probably watched and heard about enough Holocaust films to expect a formula, but you might want to put all that aside going into The Boy in Striped Pajamas. Bruno, the son of a WWII Nazi commandant forms an unlikely friendship with a Jewish kid his age in his father's concentration camp. The film is World War II told through Bruno's eyes, and while you might not get why this movie is so highly praised in its first scenes, the twisting and profound second half will have you recommending it to everyone in need of a moving story well executed, or quite simply a good cry.

Genre: Drama, Family, History, War

Actor: Amber Beattie, Asa Butterfield, Béla Fesztbaum, Cara Horgan, Charlie Baker, David Hayman, David Thewlis, Domonkos Nemeth, Gábor Harsai, Henry Kingsmill, Iván Verebély, Jack Scanlon, Jim Norton, Julia Papp, László Áron, László Nádasi, Mihály Szabados, Richard Johnson, Rupert Friend, Sheila Hancock, Vera Farmiga, Zac Mattoon O'Brien, Zsolt Sáfár Kovács, Zsuzsa Holl

Director: Mark Herman

Rating: PG-13

While the film adapts some of Shakespeare’s histories, you don’t need to know Shakespeare to appreciate My Own Private Idaho. In fact, instead of focusing on the Prince Hal character, Scott Favor (Keanu Reeves), the film centers on his narcoleptic friend Mike Waters (River Phoenix). Both of them are young street hustlers in Portland. However, unlike Favor, Waters has no reliable family, inheritance, or support system waiting for him to give up his job. Waters only has his body. Writer-director Gus Van Sant doesn’t really focus on the sex or the narcolepsy - these flash by us only as a state-of-mind experience, with time-lapses and freeze-frames to impart to us Waters’ detachment. Instead, Van Sant cares more about Waters’ seeking connection. It’s why the surreal shots speed by us so fast, and why the natural, lived-in scenes remain in our heads. It’s why Waters’ campfire confession, crackling under Phoenix’s earnest voice, feels so powerful. And it’s also why his later rejection feels so painful.

Genre: Comedy, Drama

Actor: Chiara Caselli, Eric Hull, Flea, Grace Zabriskie, Gus Van Sant, James Russo, Jessica Makinson, Jim Caviezel, Keanu Reeves, Mickey Cottrell, Pao Pei Andreoli, Pat Patterson, River Phoenix, Robert Egon, Rodney Harvey, Scott Patrick Green, Tom Troupe, Udo Kier, Vana O'Brien, William Richert

Director: Gus Van Sant

Rating: R

Done entirely in candid conversation and quiet walks around the city, End of the Century may at first come across like another mumblecore romance, but director Lucio Castro brings such a delicate touch to this story that every idle moment feels like it means the world. An unspoken longing hangs suspended between characters Ocho and Javi, and it's their little dance of disclosing more and more parts of themselves to each other that drives everything forward. And as the film reaches its miraculous third act, where hope and regret are articulated in such a painful—but kind—manner, it transcends its mumblecore inspirations and becomes its own vision of how our relationships change the way we grow.

Genre: Drama, Romance

Actor: Helen Celia Castro-Wood, Juan Barberini, Mariano López Seoane, Mía Maestro, Ramón Pujol

Director: Lucio Castro

There are moments in our childhood that we deeply regret, even if we didn’t know better, even if innocence can excuse us, and even if we weren’t the ones primarily responsible for the mistake. The memory of it can be haunting, but none has been as devastating as the memory depicted in Louis Malle’s semi-autobiographical period drama Au Revoir les Enfants. Malle brings us to the boarding school rhythms with ease, straightforwardly depicting it as is, but with the camera and the sequencing recognizant of the implications. With the natural dynamic between the unthinking Julien (Malle’s younger self) and the alert and afraid Jean formed through subtle moments, Au Revoir les Enfants culminates into the heartbreaking coming-of-age moment that Malle personally lived through in World War II.

Genre: Drama, War

Actor: Arnaud Henriet, Francine Racette, François Berléand, François Négret, Gaspard Manesse, Irène Jacob, Luc Etienne, Pascal Rivet, Peter Fitz, Philippe Morier-Genoud, Raphael Fejtö, René Bouloc, Sergio Kato, Stanislas Carré de Malberg

Director: Louis Malle

Rating: PG

The Kings of the World is a surreal coming-of-age movie that follows Rá, Culebro, Sere, Winny, and Nano, street kids who are on their way to claim land that’s rightfully theirs. Their one goal is to finally make a home after living without one for so long, but they’re hindered by the inevitable tragedies that befall kids of their kind: impoverished, alone, and abandoned.

The title is ironic, but it also hints at their state of mind: these boys are unstoppable, rabble-rousers who live like there’s no tomorrow. They tear down private property and invade inns not out of spite, necessarily, but out of a knowledge that whatever they do they’re gonna be put down anyway, so they might as well live without rules.

Tackling powerful themes like land restitution and youth neglect, The Kings of the World is one of the most agonizing movies you'll ever see. It’s also Colombia’s official Best Foreign Language Film entry in the 2022 Academy Awards.

Genre: Adventure, Drama

Actor: Brahian Acevedo, Carlos Andrés Castañeda, Cristian Campaña, Cristian David Duque, Davison Florez

Director: Laura Mora

Rating: TV-MA

Prophet’s Prey is a documentary on the sect known as Fundamentalist Latter-Day Saints and its leader, Warren Jeffs. Claiming to have inherited a direct connection to God, Jeffs has used this pretext to control a closed society of thousands of individuals on a shockingly personal level, as well as marry dozens of underage girls and harvest the community’s financial resources on behalf of “the church.”

The subject is deftly handled by filmmaker Amy Berg (Deliver Us From Evil). Here she presents most of the story via interviews with the people whose tenacity was instrumental in exposing  Jeffs. Woven throughout the film, too, is the haunting, disembodied voice of Jeffs himself, in recorded words to his followers, along with film footage of present-day FLDS communities. What emerges is the picture of a terrifying madman who still wields a disturbing amount of power over thousands of active congregants. Absolutely riveting.

Genre: Crime, Documentary, History

Actor: Nick Cave

Director: Amy J. Berg

Rating: TV-14

Told with grace and maturity without sensationalizing its subject matter, Dead Man Walking expertly walks the line between taking a moral stand and keeping the messy humanity of its characters intact. Though it may seem just like a legal drama or prison film on the surface, writer/director Tim Robbins weaves in commentary on class and the role religion is expected to play in middle class Southern communities—especially in the context of justice and crime. Sean Penn and Susan Sarandon (in the role that won her her Oscar) play every side to this drama with remarkable control, building an unlikely rapport that culminates in a finale that's as moving as any great tear-jerker. It may be tough to watch at times, given the raw emotions that are laid bare, but Dead Man Walking remains relevant even today.

Genre: Drama

Actor: Adam Nelson, Adele Robbins, Anthony Michael Frederick, Arthur Bridgers, Barton Heyman, Celia Weston, Clancy Brown, Codie Scott, Cortez Nance Jr., Dennis Neal, Eva Amurri, Eva Amurri Martino, Helen Prejean, Jack Black, Jack Henry Robbins, Jenny Krochmal, Jeremy Knaster, Joan Glover, Jon Abrahams, Kevin Cooney, Larry Pine, Lenore Banks, Lois Smith, Marcus Lyle Brown, Margo Martindale, Michael Cullen, Miles Robbins, Missy Yager, Molly Bryant, Nesbitt Blaisdell, Pamela Garmon, Pete Burris, Peter Sarsgaard, R. Lee Ermey, Ray Aranha, Raymond J. Barry, Robert Prosky, Roberta Maxwell, Scott Sowers, Scott Wilson, Sean Penn, Steve Boles, Steve Carlisle, Susan Sarandon, Thomas McGowan

Director: Tim Robbins