331 Best Depressing Movies to Watch (Page 21)

Have you got the tissues ready? Some of the most memorable watches are the ones that tug at our heart strings. Here are the best depressing movies to stream right now.

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301. Man in Love, 2021

There isn't anything about Man in Love—a remake of the 2014 South Korean film of the same name—that you haven't already seen before. But this iteration of the love story between a kindhearted woman and a scoundrel in business with gangsters and creditors benefits from high production values that help Taiwan stay romantic despite the grit of the film's plot. There's also an undeniable earnestness to even the most predictable beats here, helping the love story at its center feel more like a heat-of-the-moment bond forged in desperate economic times, and less like an abrupt bout of passion.

Genre: Drama, Romance

Actor: Chih-ju Lin, Chun Hong, Hsin-Ling Chung, Lan Wei-Hua, Lin Chih-ju, LULU Huang, Peace Yang, Roy Chiu, Tiffany Hsu, Tsai Chen-Nan, Xiao Ying Bai

Director: Chen-Hao Yin

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302. Lilya 4-ever, 2002

	
Not for the faint of heart, this Russian-language Swedish film doesn't actually display anything graphic on screen, but it still makes for a difficult and distressing viewing experience. Many films similar in spirit and subject matter have been released in the decades since Lilya 4-ever's own take on human trafficking and child sexual exploitation, which might make it less effective for new viewers. But its tone is still unique enough to set it apart—all thumping electronic/rock music blocking out the pain, and naturalistic direction that allows the film's young stars to be as authentically awkward and naively hopeful as possible.Genre: Crime, Drama
Actor: Aleksandr Okunev, Artyom Bogucharsky, Bo Christer Hjelte, Elina Benenson, Herardo Contreras, Jeff Norman, Johan Åkerblom, Liliya Shinkaryova, Lyubov Agapova, Madis Kalmet, Nikolai Bentsler, Oksana Akinshina, Oleg Rogatchov, Pavel Ponomaryov, Sten Erici, Tomasz Neuman, Tõnu Kark
Director: Lukas Moodysson

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303. Always, 2011

	
Always follows the story of Jeong-hwa and Cheol-min, both very different individuals who are gentle in their own way. The story starts off by demonstrating how different the leads are in terms of their personality and their outlook on life. The plot can be a little predictable and cliche in some moments, but Always is not a complicated movie—though in addition to being a romance, it also includes some surprising violence that may intensify your viewing experience. Still, Always is about the two leads’ struggle against fate as they try to survive their tough situations, with strong chemistry between the lead actors from start to finish.Genre: Adventure, Drama, Romance
Actor: Cho Seong-ha, Goo Seung-hyun, Han Hyo-joo, Jin Goo, Jung Jae-jin, Kang Shin-il, Kim Jung-hak, Kim Jung-pal, Kim Mi-kyeong, Kim Seon-hwa, Lee Chae-won, Lee Jin-hee, Oh Gwang-rok, Oh Kwang-rok, Park Cheol-min, Park Chul-min, Park Seong-geun, So Ji-sub, Yeom Hye-ran
Director: Song Il-gon

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304. Sometimes I Think About Dying, 2024

	
While morbidly titled, there’s an unexpected playfulness to Sometimes I Think About Dying that makes a fairly mundane office relationship into a charming romance. Writer-director Rachel Lambert and lead Daisy Ridley capture Fran’s introversion in inventive ways, with score and image to make her daydreams of death more surreal than morbid, with quiet wistfulness of someone that hasn’t quite figured out how to create casual connection. Some viewers might not jive with the way the film focuses more on visual ideas rather than plot, but Sometimes I Think About Dying sweetly depicts social awkwardness and the alluring curiosity a crush can sometimes create.Genre: Comedy, Drama, Romance
Actor: Ayanna Berkshire, Bree Elrod, Brittany O'Grady, Daisy Ridley, Dave Merheje, Jeb Berrier, Marcia DeBonis, Megan Stalter, Parvesh Cheena
Director:  Rachel Lambert
Rating: PG-13

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305. Sitting in Bars with Cake (2023)

Sitting in Bars with Cake's best qualities and roughest qualities stem from the fact that the story is apparently based on true events. Screenwriter Audrey Shulman (who based the script on her cookbook of the same title) clearly wants to honor the details of this very personal year in her life, but the effect is a story that often lacks thematic coherence. When the cancer diagnosis is inevitably revealed, the rest of the film's subplots just seem frivolous and underdeveloped in comparison. But there's also a charm to having this be a story about a friendship rooted in regular, random things—suddenly interrupted by a devastating illness. The film definitely doesn't escape the cliches of a cancer drama, but they're deployed in a more sedate, mature way here. And if the filmmaking doesn't do much to tell this story in a more interesting way, the performances are enough to let the emotions land when they really need to.

Genre: Comedy, Drama, Romance

Actor: Bette Midler, Maia Mitchell, Odessa A'zion, Ron Livingston, Yara Shahidi

Director: Trish Sie

Rating: PG-13

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306. Mast Mein Rehne Ka, 2023

	
You'd expect a film with a premise like this to make constant parallels between its two main storylines, or to at least have them intersect more often and more significantly. But impressively, Mast Mein Rehne Ka makes the jump from chance encounter to wandering slice-of-life drama with ease—becoming a portrait of Mumbai and the isolation that various people experience due to discrimination against their class, their age, or their gender. The film's tonal balance certainly isn't perfect, as the more lighthearted adventures of the widower begin to clash more severely with the literal life-or-death situations faced by the young would-be thief. But consistently solid filmmaking and heartfelt performances smooth over the rougher edges and the occasional bits of dramatic excess.Genre: Comedy, Drama
Actor: Abhishek Chauhan, Faisal Malik, Jackie Shroff, Mashhoor Amrohi, Monika Panwar, Neena Gupta, Priyadarshan Jadhav, Rakhi Sawant, Shashi Kiran, Uday Sabnis, Vijay Maurya
Director: Vijay Maurya

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307. I Used to Be Funny, 2024

	
In the same festival where she showcased her screenwriting chops, Rachel Sennott also showcased her dramatic side in I Used to Be Funny, a difficult drama that garnered less acclaim than Bottoms (2023). It’s understandable– while both films have a witty, gen-Z slant in its comedy, this drama is much harder to balance and heavy to watch, dealing with mental health and PTSD. The non-linear narrative occasionally does make the film feel a tad disjointed as well. However, there’s a care and a warmth from Ally Pankiw’s direction that makes this exploration of Sam’s complex trauma feel heartfelt, and Sennott holds each scene with compelling charisma.Genre: Comedy, Drama
Actor: Caleb Hearon, Dan Beirne, Dani Kind, Ennis Esmer, Hannah Spear, Jason Jones, Kathy Imrie, Matia Jackett, Miguel Rivas, Olga Petsa, Rachel Sennott, Sabrina Jalees
Director: Ally Pankiw
Rating: NR

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308. The Village, 2023

Yu Katayama lives in a remote village with a garbage disposal business that's slowly turning into a landfill. When his childhood friend Misaki Nakai returns to the village, she encourages Yu to make a better life for himself despite his mother's gambling and the village ostracizing him. The Village is a slow-burning film interested in Yu's struggles as an outcast and in discussing the takeover of small villages for capitalistic industrial motives. The film is shot beautifully with dark, brooding visuals and lingering shots of Yu's quiet intensity throughout the film. Unfortunately, secondary characters are not fully developed outside of their interactions with Yu, causing the film to feel flat outside of pivotal moments. An evocative idea with parts more memorable than the whole.

Genre: Drama

Actor: Arata Furuta, Daiken Okudaira, Hana Kino, Haru Kuroki, Naomi Nishida, Ryusei Yokohama, Ryūto Sakuma, Sakuma Ryuto, Shidô Nakamura, Tetta Sugimoto, Wataru Ichinose

Director: Michihito Fujii

Rating: R, TV-MA

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309. Six Schizophrenic Brothers, 2024

Even in a bloated genre like true crime, Six Schizophrenic Brothers manages to be shocking because of its horrifying premise. It’s about a family that had to deal not just with the titular illness, but with multiple and chronic cases of abuse, rape, incest, and murder. And perhaps the most amazing part of it all is that director Lee Phillips was able to gather many of the siblings and have them tell the story themselves. So it’s a baffling shame that Phillips also had to lean on cheesy visual and sound effects to sensationalize an already appalling story. Whenever someone reveals a hard truth, glass shatters and fans are flamed. Whenever one of the ill siblings is introduced, they’re accompanied by sinister sounds and backgrounds. Then there are the questions he asks them, which are more exploitative than insightful. It’s true that the documentary, like watching a fire, is an engrossing experience that’s difficult to look away from. But in this case, the terror comes both from the story and the awful editing choices.

Genre: Documentary

Rating: TV-14

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310. Hurricane Season, 2023

The atmosphere communicated within the title Hurricane Season comes off incredibly clearly on screen: this is a film that just feels humid and full of foreboding for a coming storm, with people feeling all manner of guilt while secluded in their own homes. Cinematographer María Secco's gorgeous colors and brown tones fill the 4:3 aspect ratio nicely, and director Elisa Miller lets events unfold with the stately pace of a long novel. There's something fascinating here about how each new "chapter" or perspective doesn't really lead to more answers, but simply to more anguish closing in from all sides.

So it would be understandable if some may be put off by how unrelentingly dark Hurricane Season is, especially as the trans woman whose death becomes the central event never enjoys the kind of characterization everybody around her gets. Apart from how the film illustrates that discrimination against women, against repressed "taboo" sexuality, and against access to proper reproductive health only threatens to grow under poverty, it can be difficult to grasp what point the movie is trying to make. Social realism certainly has its place in cinema, but the different perspective in this particular film still don't add up to more than the sum of its parts.

Genre: Crime, Drama, Thriller

Actor: Andrés Cordaz, Edgar Treviño, Flor Eduarda Gurrola, Guss Morales, Kat Rigoni, Mónica Martínez, Norma Reyna, Paloma Alvamar, Rodrigo Corea, Said Sandoval

Director: Elisa Miller

Rating: R

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311. A Thousand Cuts, 2020

The level of access that A Thousand Cuts gets to both the side of the press and of the administration is ultimately what makes it valuable. By being on the ground with journalists doing honest-to-goodness hard work, the film reframes Duterte's war on drugs (really a campaign to terrorize the poor into submission) as an information war between news outlets and government propaganda. Unfortunately, in the process, the film also winds up excluding the voices of working class people and how they both engage and are engaged by all this information. There should be a way to honor the work of these journalists without accidentally positioning them above the public they serve.

Genre: Documentary

Actor: Amal Clooney, George Clooney, Leni Robredo, Maria Ressa, Patricia Evangalista, Pia Ranada

Director: Ramona S. Diaz

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312. Scouts Honor: The Secret Files of the Boy Scouts of America, 2023

Depressingly, Scout's Honor isn't necessarily an exposé about the crimes of the Boy Scouts of America because—as the documentary reminds us—this institution has been caught red-handed many times over since its inception, and yet it evades real accountability. The film is more like a renewed call for justice, with its approach being one of blunt force. This means that the documentary can be sloppy, piling on one case after another without much synthesis, and taking out its anger on one current representative of the Boy Scouts, whom the filmmakers constantly interrupt and interrogate during his interview, That said, it's also hard to object to this kind of approach, as the patterns of abuse become too damning to ignore. Maybe a different film will be able to unpack the systems that allow the Boy Scouts to get away with this, but for now this cry of rage is enough.

Genre: Crime, Documentary

Director: Brian Knappenberger

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313. Phoenix: Eden17, 2023

	
Based on an arc of the classic Space Age manga, Phoenix: Eden17 reimagines the future of space exploration into a contemplation of human nature. While the show’s pacing speeds through its plot points within four episodes, each reveal feels gut wrenching, as Romi consistently has to deal with changes in Eden, Earth, and what happened to her loved ones. Modern-style animation is used, but inspired the original style of its time, creating a modernized version of the original mangaka Osamu Tezuka’s stunning images. But it’s the series’ ideas that make the show unique. Greed, betrayal, isolation, and human error causes all the disasters in this show’s universe, and even when you know it’s coming, it’s still hard not to feel the devastation the characters feel. Despite being based on a manga created decades ago, Phoenix: Eden17 still feels like an entirely singular work. Given modern animation, the ideas of the father of manga feel like it’s something never seen before.Genre: Animation
Actor: Honoka Yoshida, Issey Ogata, Rie Miyazawa, Ryohei Kimura, Shintaro Asanuma, Yosuke Kubozuka
Director: Shoujirou Nishimi
Rating: TV-MA

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314. The Beast in the Jungle, 2023

	
Transporting the Henry James novella to the nightclub, The Beast in the Jungle turns the Edwardian era story into a surreal, escapist drama spanning the last decades of the 20th century. As John and May wait for that all-important event, they lose the importance of everything else, like love, friendship, and family, all to the decadence they only acknowledge as patience. This concept paired with the visuals are interesting, especially since the film also makes the viewer wait with them, drawing out the existential frustration, the fear of a life not lived, and the self-absorption, but the film struggles with the historical events, haphazardly inserting tragedies like the AIDS epidemic for what seems to be no reason.Genre: Drama
Actor: Anaïs Demoustier, Bachir Tlili, Béatrice Dalle, Mara Taquin, Martin Vischer, Tom Mercier
Director: Patric Chiha

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315. RedLife, 2023

	
There’s a sense of disconnectedness in RedLife, as the film isn’t centered on one storyline, but rather two storylines that at first don’t seem connected. Ter, a young snatcher, marries a sex worker named Mild, while Som is a student who aspires to escape her prostitute mom’s poverty, especially after she falls for the more affluent Peach. At first, the film depicts their lives in stunningly framed, slice-of-life moments that captures a different side of Bangkok, one that’s tough to depict, but one people know about. But they do intersect, later on in the movie, in a series of events that leads them trapped in tragedy, despite all they did to escape it. The unexpected twist makes their lives surprisingly poignant, though RedLife’s journey might take too long to get there.Genre: Drama, Thriller
Actor: Banlop Lomnoi, D Gerrard, Karnpicha Pongpanit, Krongthong Rachatawan, Pimvipa Thanarapatvanich, Punyapat Wangpongsathaporn, Ray MacDonald, Sumitra Duangkaew, Supitcha Sangkhachinda, Tanapak Jongjaiphar, Thiti Mahayotaruk
Director: Ekalak Klunson

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