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The 45 Saddest Movies of All Time (Esquire)

Sometimes, when you're feeling low, the only way to cheer yourself up is to sulk. Yes, sulk. Rot. Brood. Whatever you want to call it. I'm not here to tell you to lift your chin up and persevere. All that does is delay the inevitable—and we know you don't have time to waste. Just feel your feelings!
What better way to get your sad juices flowing than by curling up on the couch and pressing play on a truly devastating film? Watching sad movies has a uniquely cathartic effect. If you can relate to a character's issues, you'll find that there's always light at the end of the tunnel. (That's the power of a three-act structure, people!) And if you can't? Well, hey! At least your problems aren't that bad.
In all seriousness, we're here to help you get through whatever has you down. Below, we've rounded up the saddest movies of all time. Whether you're in the mood for a sad history lesson, romance, or tale of redemption—we have you covered.
516 users · 920 views
 
from esquire.com · made by Konehead Cokehead
avg. score: 14 of 45 (31%)
required scores: 1, 7, 11, 14, 20 

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1
Still Alice (2014)
Still Alice (2014)
2
May December (2023)
May December (2023)
3
The Pursuit of Happyness (2006)
The Pursuit of Happyness (2006)
4
Past Lives (2023)
Past Lives (2023)
5
Dallas Buyers Club (2013)
Dallas Buyers Club (2013)
6
Cinema Paradiso (1988)
Cinema Paradiso (1988)
7
50/50 (2011)
50/50 (2011)
8
Lost in Translation (2003)
Lost in Translation (2003)
9
Steel Magnolias (1989)
Steel Magnolias (1989)
10
Can You Ever Forgive Me? (2018)
Can You Ever Forgive Me? (2018)
11
Into the Wild (2007)
Into the Wild (2007)
12
Manchester by the Sea (2016)
Manchester by the Sea (2016)
13
Remember the Titans (2000)
Remember the Titans (2000)
14
The Banshees of Inisheer (2022)
The Banshees of Inisheer (2022)
15
Midsommar (2019)
Midsommar (2019)
16
Moonlight (2016)
Moonlight (2016)
17
Son of Saul (2015)
Son of Saul (2015)
18
Dead Poets Society (1989)
Dead Poets Society (1989)
19
In the Mood for Love (2000)
In the Mood for Love (2000)
20
The Florida Project (2017)
The Florida Project (2017)
21
Love Story (1970)
Love Story (1970)
22
Schindler's List (1993)
Schindler's List (1993)
23
Requiem for a Dream (2000)
Requiem for a Dream (2000)
24
Brokeback Mountain (2005)
Brokeback Mountain (2005)
25
My Girl (1991)
My Girl (1991)
26
Sophie's Choice (1982)
Sophie's Choice (1982)
27
Precious (2009)
Precious (2009)
28
The Green Mile (1999)
The Green Mile (1999)
29
Life Is Beautiful (1997)
Life Is Beautiful (1997)
30
Roma (2018)
Roma (2018)
31
Fruitvale Station (2013)
Fruitvale Station (2013)
32
Loving Vincent (2017)
Loving Vincent (2017)
33
The Umbrellas of Cherbourg (1964)
The Umbrellas of Cherbourg (1964)
34
Lenny Cooke (2013)
Lenny Cooke (2013)
35
Umberto D. (1952)
Umberto D. (1952)
36
The Farewell (2019)
The Farewell (2019)
37
Grave of the Fireflies (1988)
Grave of the Fireflies (1988)
38
Call Me by Your Name (2017)
Call Me by Your Name (2017)
39
Twenty-Four Eyes (1954)
Twenty-Four Eyes (1954)
40
Titanic (1997)
Titanic (1997)
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