The 20 best sad movies streaming on Max right now

Keep a box of tissues handy when watching these films.

Sometimes you just know a movie is going to make you cry. There may be hints in the plot description that point to your tear ducts getting all worked up. But more often than not, a satisfying sad movie resonates with a specific time and place in your own life.

Max has more than its fair share of sad movies; some might make you ugly cry, while others may inspire tears of joy. Whether you’re in the mood for medical dramas like My Sister’s Keeper and Still Alice or want to wallow in the tragic romances of A Ghost Story and Moonlight, the streamer has many titles to tug on your heartstrings.

Here are the 20 best sad movies on Max right now.

20th Century Women (2016)

It’s a testament to Mike Mills’ delicate directorial touch that, for a movie where one woman battles cancer and another keeps mentioning her Depression-era upbringing, 20th Century Women isn’t depressing. Instead, twinges of melancholy and loss pervade the work; it’s sad the way an old photograph or happy memories of your mom are sad. Mills’ late mother is the basis for Dorothea (Annette Bening), who raises her teenage son in 1970s Santa Barbara. His subsequent coming-of-age story feels lived-in, with gauzy nostalgia for a time, place, and group of people fading into history.

Where to watch 20th Century Women: Max

EW grade: A- (read the review)

Director: Mike Mills

Cast: Annette Bening, Greta Gerwig, Elle Fanning, Lucas Jade Zumann, Billy Crudup

Related content: Annette Bening on 20th Century Women, a role that hits close to home

Amy (2015)

Documentaries about iconic artists — many of them overly flattering or voyeuristic — are a dime a dozen. But some filmmakers resist the temptation to reshape legacies for the sake of a narrative, and Asif Kapadia’s Amy is a stunning example. (We can only hope the upcoming biopic Back to Black will pay similar heed.) It’s a blunt and intimate portrait of the sensational Amy Winehouse, a musician whose hard-knock backstory and fatal vices were known even before her untimely death at age 27. She was a generational talent who couldn’t outrun her demons, and the weight of mortality and fate hovers over every frame.

Where to watch Amy: Max

EW grade: A (read the review)

Director: Asif Kapadia

Related content: Back to Black movie reveals Industry star's transformation into Amy Winehouse

Bicycle Thieves (1948)

The defining accomplishment of Italy’s neorealist period, Bicycle Thieves is deceptively simple: A man gets a job. To do it, he needs a bike. Another man steals his bike. As a moral premise, this is easy, right? After all, Antonio (Lamberto Maggiorani) has a young son and a newborn to feed. But the film’s profundity lies in its understanding that the thief, like so much of postwar Italy’s working class, is in the same boat as Antonio. In other words, the desperation is circular. It’s inevitable that, eventually, Antonio will be desperate enough to steal a bike himself, which is just one of the film’s many brutal ironies.

Where to watch Bicycle Thieves: Max

Director: Vittorio De Sica

Cast: Lamberto Maggiorani, Enzo Staiola, Lianella Carell

Related content: 5 Italian cinema classics to watch after Master of None — and where to find them

Crazy Heart (2009)

There’s no “new” way to tell a story like Crazy Heart, just like there’s no “new” way to write a sad country ballad. But this movie, which earned Jeff Bridges his first Oscar, knows the storytelling traditions it belongs to: the boozy, past-his-prime crooner with a chance at a comeback and maybe a shot at love. One of the film’s costars, Robert Duvall, won his Oscar for a variation of that same story, Tender Mercies (1983). But thanks to the performances by Bridges and Maggie Gyllenhaal, Crazy Heart doesn’t feel like a retread. And when it goes to dark places, they never feel unearned.

Where to watch Crazy Heart: Max

EW grade: B+ (read the review)

Director: Scott Cooper

Cast: Jeff Bridges, Maggie Gyllenhaal, Robert Duvall, Colin Farrell

Related content: Jeff Bridges: (Finally!) An Oscar winner

Definitely, Maybe (2008)

Deadpool has occasionally shown some sensitivity. That side of Ryan Reynolds has never been put to better use than in Definitely, Maybe, which is equal parts tearjerker and romantic comedy. Will (Reynolds) is a soon-to-be-divorced dad telling his daughter Maya (Abigail Breslin) about how he met her mother. With refreshing honesty, the film focuses on failures and what-ifs — unexpected breakups, missed connections, bad timing. It’s about the unromantic reality that, more often than not, things don’t work out. But there are silver linings, like a precocious daughter you get to share your stories with. The film earns its tears, but they’re happy tears.

Where to watch Definitely, Maybe: Max

EW grade: B+ (read the review)

Cast: Ryan Reynolds, Isla Fisher, Elizabeth Banks, Abigail Breslin, Rachel Weisz, Kevin Kline

Related content: The 25 best romantic comedies on Max

Dope Sick Love (2005)

Dope Sick Love gets its power from its powerlessness. This unfiltered depiction of two drug-addict couples on the streets of New York — hustling, scoring, surviving — isn’t framed by an inspiring message of recovery. There are no talking-head interviews putting addiction into a moral context, nor are there romanticized vagabonds. Instead, the camera simply observes these lives, which are astonishing in their ugliness, danger, and dread. The very idea of intervention — by filmmakers, by medical professionals, or by family members on the periphery of these addicts’ lives — is a no-go. What makes the documentary so affecting is that it simply refuses to look away.

Where to watch Dope Sick Love: Max

Director: Felice Conte, Brent Renaud, Craig Renaud

Related content: Filmmaker Brent Renaud shot and killed in Ukraine while making refugee documentary

Eighth Grade (2018)

The sense of not belonging — and wanting to fit in, be seen, and be accepted — is never more pronounced than in mid-adolescence, that awkward middle school era which, for many, contains the most painful years. Few films capture that feeling better than Bo Burnham’s Eighth Grade. The story follows Kayla (Elsie Fisher), a timid teenager still trying to find herself during the final week of school. No pain hits quite like eighth-grade pain. No embarrassment hits quite like eighth-grade embarrassment. This is the sad, ugly truth that Burnham — and his lead actress — seem to understand implicitly.

Where to watch Eighth Grade: Max

EW grade: A (read the review)

Director: Bo Burnham

Cast: Elsie Fisher, Josh Hamilton, Emily Robinson, Jake Ryan

Related content: Bo Burnham originally thought no one would ever take Eighth Grade seriously

Every Brilliant Thing (2016)

Every Brilliant Thing, the HBO recording of British comedian Jonny Donahoe’s one-man show, takes pleasure in the little things. The conceit is simple and strangely moving: a young boy creates a list of things that make life worth living to cheer up his depressed mother who attempted suicide. The performance invites the audience to participate, reading out various bits from the list — “the smell of old books” is one, “sunlight” another — and finding joy in the small things that populate our daily lives. The show’s inherent sorrow is alleviated by Donahoe’s sense of hope, humor, and the notion that being alive is beautiful.

Where to watch Every Brilliant Thing: Max

EW grade: A- (read the review)

Director: Fenton Fox Bailey, Randy Barbato

Cast: Jonny Donahoe

Fruitvale Station (2013)

A year before the deaths of Eric Garner and Michael Brown gave racialized police violence the mainstream visibility it had long lacked, and seven years before George Floyd’s killing took that awareness to another level, Ryan Coogler teamed with Michael B. Jordan to tell the story of Oscar Grant, a 22-year-old who was killed by a transit officer in Oakland in 2009. What makes Fruitvale Station sting so much is Coogler’s doggedly ordinary slice-of-life approach. He paints a realistic portrait of a young man going about his day — running his errands, visiting his daughter — which ultimately ends with his death under painfully avoidable and unjust circumstances.

Where to watch Fruitvale Station: Max

EW grade: A (read the review)

Director: Ryan Coogler

Cast: Michael B. Jordan, Melonie Diaz, Kevin Durand, Chad Michael Murray

Related content: Michael B. Jordan and Ryan Coogler on the harrowing tragedy of Fruitvale Station

A Ghost Story (2017)

C (Casey Affleck) died in a car accident, leaving behind his wife, M (Rooney Mara). Covered in a white sheet, he lingers and watches as she moves on, moves out, and makes way for new tenants to move in. The more temporal distance he gets from life on Earth, the more slippery the idea of time becomes. Years, decades, and centuries pass. Still he remains — still in the same physical space, still in that white sheet — but lost and confused. There’s a specific wrinkle that should go unspoiled, but suffice it to say David Lowery’s approach to loss and memory is not purely linear, as A Ghost Story finds an entirely new way to mourn and understand mourning.

Where to watch A Ghost Story: Max

Director: David Lowery

Cast: Rooney Mara, Casey Affleck, Will Oldham

Good Will Hunting (1997)

Good Will Hunting follows the brilliant, stubborn Will Hunting (Matt Damon) who learns to embrace his potential with the help of a kind-hearted therapist (Robin Williams). There are too many crowd-pleasing moments for this to be a total downer, but it doesn’t shy away from pain and trauma. Dr. Maguire’s memories of his late wife hit both hilarious and devastating notes, and the resentments between him and his old friend, Professor Lambeau (Stellan Skarsgård), strike a painful chord. Will’s life will probably turn out alright, but the film’s lingering sadness concerns those he leaves behind — namely best friend Chuckie (co-writer Ben Affleck) — even though they know it’s for the best.

Where to watch Good Will Hunting: Max

EW grade: B (read the review)

Director: Gus Van Sant

Cast: Matt Damon, Ben Affleck, Minnie Driver, Robin Williams, Stellan Skarsgård

Related content: Ben Affleck and Matt Damon credit Kevin Smith for saving Good Will Hunting

In the Mood for Love (2000)

No film has ever ached quite like In the Mood for Love. Mr. Chow (Tony Leung) and Mrs. Chan (Maggie Cheung) are doomed, seeking each other’s company because their unfaithful spouses aren’t around. A shared loneliness evolves into an overwhelming need, but their love can never be spoken or acted upon, hiding underneath a thin façade in polite society circa 1962. There's a good reason this is considered one of the best movies ever made, and if any romance is likely to consume you with regret for the one that got away, this is it.

Where to watch In the Mood for Love: Max

EW grade: B+ (read the review)

Director: Wong Kar-wai

Cast: Tony Leung, Maggie Cheung, Rebecca Pan

Related content: Wong Kar-wai was in the mood for conversation at MOMA book chat

The Iron Claw (2023)

The true story of the Von Erich wrestling family was so unrelentingly tragic that when The Iron Claw finally got made, director Sean Durkin opted to leave one brother out entirely. (He later told EW that call was “one of the toughest decisions I had to make.”) The film has more than its share of anguish, but that’s no reason for audiences to avoid it. There’s joy in the bonds of brotherhood shared between the Von Erichs, in and out of the ring, even amid their darkest moments. And the movie makes room for hope, particularly embodied by Kevin (Zac Efron in a career-best performance).

Where to watch The Iron Claw: Max

Director: Sean Durkin

Cast: Zac Efron, Holt McCallany, Harris Dickinson, Lily James, Jeremy Allen White, Maura Tierney

Related content: Into the ring: The Iron Claw stars talk dropkicks and their emotional wrestling drama

Leaving Las Vegas (1995)

That the writer of Leaving Las Vegas took his own life is sadly informative about the film his book became. The novel, as EW wrote in 1995, is essentially a “189-page suicide note.” True to that spirit, Ben (Nicolas Cage) has only one ambition: to drink himself to death. He’s lost his family and his purpose and sees no reason to keep going. Even when he bonds with the kind, beautiful sex worker Sera (Elisabeth Shue), he makes it clear that he’s not meant for this world. Though there’s a surprising degree of levity, this is ultimately a bleak, unrelenting film.

Where to watch Leaving Las Vegas: Max

EW grade: A- (read the review)

Director: Mike Figgis

Cast: Nicolas Cage, Elisabeth Shue, Julian Sands

Related content: The best Nicolas Cage roles

Mid90s (2018)

Jonah Hill’s coming-of-age drama manages to capture all the joys and sorrows of a certain time, place, and adolescent stage. The film follows Stevie (Sunny Suljic), a 13-year-old who finds acceptance with a group of older skateboarders. In his directorial debut, Hill nails the ecstatic but intimidating feeling of finding a social group when every other support system fails you. Stevie doesn’t fit in with other kids, his older brother isn’t nice to him, and his mom is, like many single mothers in movies, overworked and time-deprived. What distinguishes Mid90s from its predecessors is the lack of romanticized nostalgia; it accepts the hardships — and bruises, and broken bones — of growing up.

Where to watch Mid90s: Max

EW grade: A- (read the review)

Director: Jonah Hill

Cast: Sunny Suljic, Lucas Hedges, Na-Kel Smith, Olan Prenatt, Katherine Waterston

Moonlight (2016)

It says a lot about how attuned Moonlight is to its protagonist that one small, poignant revelation arguably hits harder than anything else. Having reunited with Kevin (André Holland), the man who was his first romance years ago, Chiron (Trevante Rhodes) admits: “I haven’t touched anyone since.” In that moment, we see the same scared boy from the film’s opening chapter — the child found and cared for by Juan (Mahershala Ali) because his drug-addicted mother couldn’t. The scene gets to the heart of what makes Barry Jenkins’ Best Picture winner so special: There’s misfortune, betrayal, and violence throughout Chiron’s life, yet it’s the small, intimate details that reveal his true vulnerability.

Where to watch Moonlight: Max

EW grade: A (read the review)

Director: Barry Jenkins

Cast: Mahershala Ali, Trevante Rhodes, Naomie Harris, Ashton Sanders, André Holland, Janelle Monae

Related content: Moonlight: Mahershala Ali on why the movie matters

My Sister’s Keeper (2009)

My Sister’s Keeper is built on a certain moral, medical calculus. A couple (Cameron Diaz and Jason Patric) has a daughter (Sofia Vassilieva) who was born with leukemia. To help save her life, they decide to have a “savior sister” (i.e. a child conceived through IVF to be a genetic match for donating blood and stem cells). That sister, Anna (Abigail Breslin), is the film’s emotional and ethical centerpiece, as her bodily autonomy becomes the basis of a lawsuit against her own parents. The film does not have easily satisfying answers or solutions. Simply by the nature of its premise, it rarely lets its characters or their emotional contradictions off the hook.

Where to watch My Sister’s Keeper: Max

Director: Nick Cassavetes

Cast: Cameron Diaz, Abigail Breslin, Jason Patric, Alec Baldwin, Joan Cusack

Related content: I'm Still Not Over... the ending switch in My Sister's Keeper

Ordinary People (1980)

Ordinary People’s inciting incident is every parent’s worst nightmare: the death of a child… followed by the attempted suicide of another child (Timothy Hutton). Robert Redford’s directorial debut only gets thornier from there, if only because, perhaps for the first time in this otherwise privileged family’s life, they have to confront certain harsh truths about themselves and each other. The film’s authenticity allows it to go to uncomfortable places. Here, even the things we take for granted — a couple’s understanding of one another; a mother’s feelings toward her child — aren’t as simple as we expect.

Where to watch Ordinary People: Max

Director: Robert Redford

Cast: Donald Sutherland, Mary Tyler Moore, Judd Hirsch, Timothy Hutton

Related content: Robert Redford shares stories about his most iconic roles

Room (2015)

There’s no comfortable way to tell a story like Room. Even as Joy (Brie Larson) and her 5-year-old son Jack (Jacob Tremblay) escape after years of being held in captivity by her abductor and rapist, their triumphant freedom brings a bittersweet realization: The life that awaits them won’t be easy. Trauma doesn’t just go away like a flipped switch once the worst is over. Joy wants to create a beautiful life for her son, but he has no understanding of the world. They’re back at square one. It’s a testament to Tremblay and Larson, who won the Oscar for Best Actress, that there’s so much light within one of the darkest films in recent memory.

Where to watch Room: Max

EW grade: A (read the review)

Director: Lenny Abrahamson

Cast: Brie Larson, Jacob Tremblay, Joan Allen, William H. Macy

Related content: Make Room for Brie Larson

Still Alice (2014)

Weepy dramas about terminal illnesses are common, but Still Alice is sentimental without being saccharine. Alice Howland (Julianne Moore in an Oscar-winning turn) is a successful professor who’s still arguably in her prime — until she’s diagnosed with early-onset Alzheimer’s at age 50. The film doesn’t lay on the melodrama too thick, but accepts the situation as a matter-of-fact, if terrifying, reality. Alice has to reckon with her fading memory (which is to say, her fading identity) in a way that underscores the cruel, random frailty of our minds, bodies, and mortality.

Where to watch Still Alice: Max

EW grade: B+ (read the review)

Director: Richard Glatzer, Wash Westmoreland

Cast: Julianne Moore, Alec Baldwin, Kristen Stewart, Kate Bosworth

Related content: Julianne Moore talks with EW's Nicole Sperling about her research for Still Alice

Read the original article on Entertainment Weekly.