A Definitive Guide to the 20 Saddest Movies of All Time

Doesn't make them any less beautiful, though.

Updated on December 8th, 2023 by Louise Everitt: This article has been updated with additional content to keep information relevant. We've added some of the latest titles released in 2023 to keep things up-to-date and interesting for you. Dive in and check out what's new!

1. Shayda (2023)

In "Shayda," a brave Iranian mother, fleeing from her troubled past, finds solace and a new beginning in an Australian women's shelter, where she and her six-year-old daughter strive to rebuild their lives and identity during the Persian New Year​​.

2. Are You There God? It's Me, Margaret (2023)

The movie, based on Judy Blume's classic novel, tells the story of a young girl named Margaret. She is going through a lot of changes as she grows up, figuring out her beliefs and who she is. The film shows her experiences and thoughts in a really honest way, as she tries to understand herself better.

3. Fallen Leaves (2023)

Set against the backdrop of modern-day Helsinki, "Fallen Leaves" tells the poignant story of two lonely individuals who, seeking love and connection, find their paths unexpectedly intertwined in a local karaoke bar, only to discover that love can be as unpredictable as it is beautiful​​.

4. Rye Lane (2023)

"Rye Lane" focuses on Yas and Dom, two young Londoners who, each nursing the wounds of a recent breakup, embark on a serendipitous adventure through the vibrant streets of South London, finding laughter, healing, and perhaps a new beginning in each other's company​​.

5. Joyland (2023)

The film "Joyland" delves into the lives of the Ranas, a traditionally patriarchal Pakistani family whose deepest desire is the birth of a male heir, but their world is upended when their youngest son falls in love with a transgender woman, challenging their long-held beliefs and societal norms​​.

6. Schindler's List (1993)

Remember that haunting black and white image of the little girl in a red coat? Steven Spielberg 's historical drama tells the story of Oskar Schindler, a German businessman who saved more than a thousand Polish-Jewish refugees during the Holocaust. Using his own money and a lot of wit, Schindler convinces the Nazis to let him keep these 'essential workers'. It's one of those films that's heavy on facts but never skimps on heart.

7. Beaches (1988)

"Wind Beneath My Wings," anyone? Beaches is the quintessential story of two lifelong friends, played by Bette Midler and Barbara Hershey. Their bond starts in childhood, and we're taken on a ride through their ups and downs, their triumphs, and disagreements. The real tear-jerker? When one faces a terminal illness, and the other steps up in the most heartfelt way possible.

8. Grave of the Fireflies (1988)

An animated film? Really? But hang on, this isn't your regular Saturday morning cartoon. Set in World War II Japan, it chronicles siblings Seita and Setsuko as they fight for survival after losing their mother in an air raid. What's worse than watching kids starve? Maybe watching them light fireflies in a cave to lift their spirits. It's touching in a 'make you ugly cry' kind of way.

9. Marley & Me (2008)

It starts off all sunshine and daisies with a couple (Jennifer Aniston and Owen Wilson) adopting a mischievous golden retriever named Marley. The duo goes through the usual hiccups of dog parenting, but as Marley gets older, well, we all know where this is going. Remember that time when Marley enjoyed a beach day, running and playing? Hit me right in the feels.

10. Romeo + Juliet (1996)

You probably had to read the Shakespeare play in school, but Baz Luhrmann 's modern-ish adaptation is something else. Leonardo DiCaprio and Claire Danes? '90s heartthrob meets Shakespearean tragedy! Two young lovers from feuding families can't keep their hands off each other, leading to miscommunications, secret plans, and, yep, you guessed it, a double dose of heartache in the end. Why couldn't they just text each other?

11. Atonement (2007)

Ever told a white lie that spiraled out of control? That's kind of the vibe in Atonement. It starts with a budding romance between Cecilia (Keira Knightley) and Robbie (James McAvoy). But Cecilia's younger sister, Briony, misinterprets something she sees, leading to accusations and Robbie getting sent off to war. Years later, Briony tries to make amends, but some things just can't be undone.

12. The Green Mile (1999)

It's always interesting when something supernatural mixes with deep human emotions. Set on death row, Tom Hanks plays a guard who encounters John Coffey (Michael Clarke Duncan), a giant man with magical healing powers. As we delve into Coffey's backstory, we're left questioning the fairness of the justice system and the kindness of human nature.

13. My Girl (1991)

Childhood friendships, first kisses, and... bees? Vada (Anna Chlumsky) and Thomas (Macaulay Culkin) are inseparable. She's obsessed with death (her dad runs a funeral home) and he's allergic to everything. One day, trying to retrieve Vada's lost mood ring, Thomas has a run-in with a beehive. You can guess the aftermath. A somber lesson on life and loss, wrapped up in a coming-of-age bow.

14. Brokeback Mountain (2005)

Mountains, cowboys, and forbidden love. Ennis (Heath Ledger) and Jack (Jake Gyllenhaal ) are two ranch hands who form a bond one summer. Despite going their separate ways, getting married, and having families, their connection remains strong. But the 60s wasn't the friendliest time for LGBTQ+ relationships. It's about loving deeply and the personal sacrifices we sometimes make.

15. Terms of Endearment (1983)

Ever have those moments when you just can't stand your mom but love her to pieces at the same time? This one's a roller coaster ride (not to use that term lightly) through 30 years of a mother-daughter relationship. With stars like Shirley MacLaine and Jack Nicholson, it's got humor, it's got drama, but when a health crisis strikes, well, make sure you've got tissues nearby.

16. The Boy in the Striped Pajamas (2008)

Set during the Holocaust, this film revolves around the unlikely friendship between an eight-year-old German boy, Bruno, and a Jewish boy named Shmuel who wears the "striped pajamas" of a concentration camp inmate. The two meet at a fence where they begin their secret chats. The ending? Just a word of advice, it's not a 'watch-with-kids' kind of movie.

17. Million Dollar Baby (2004)

Boxing isn't all about the punches. Clint Eastwood is a trainer, and Hilary Swank is a fighter with a dream. She's fierce, she's ambitious, and she's quickly rising to the top. But a tragic accident in the ring changes everything. If this doesn't tug at your heartstrings, I don't know what will.

18. Manchester by the Sea (2016)

Can you imagine being forced to take care of your nephew after your brother's death? That's the situation Casey Affleck's character faces. Oh, and did I mention he's dealing with immense personal guilt over a past tragedy? It's not just about loss, but about finding a way (or not) to live with it.

19. Sophie's Choice (1982)

Set in post-WWII Brooklyn, Meryl Streep plays Sophie, a Polish immigrant with a haunting secret from her past in Auschwitz. Through flashbacks, we get to see the heart-wrenching decision she had to make between her two children. The title isn't just catchy; it's deeply, profoundly sad.

20. The Pianist (2002)

Adrien Brody stars as Władysław Szpilman, a Polish-Jewish pianist during WWII. This film paints a detailed picture of his survival amidst the Warsaw Ghetto Uprising. The scene where he plays the piano after years, in an abandoned home? Bone-chillingly sorrowful.