Some SPOILERS lurk beyond this point.
10. Philadelphia (1993)
I'd call Jonathan Demme's bittersweet courtroom drama the closest thing to an uplifting film on the list. After all, Andrew Beckett wins the case, marking a huge triumph against sexuality-based discrimination, but the gradual and inevitable deterioration of his condition over the course of the movie due to AIDS is an agonizing, almost dirge-like march. The final scene – his wake, set to Neil Young's Oscar-nominated song “Philadelphia” – is five-hankie filmmaking.
9. Hud (1960)
Paul Newman's portrayal of Hud, the self-centred central character of Martin Ritt's dusty drama, is hardly a sympathetic one, but the arc of his father, the principled old cattleman who clings to the traditions of the past, always wins my pathos. Melvyn Douglas is heartbreaking in this role, and is especially moving when forced to exterminate his beloved cattle due to foot-in-mouth disease. One can't help but wonder if the shots he personally fires at his last two Texas longhorns isn't some form of suicide.
8. Au revoir, les enfants (1987)
While the Holocaust has been depicted through the eyes of children in several literary works, few motion pictures have managed to capture that juxtaposition of innocence and atrocity with the same dramatic essence. This is the exception, a highly personal account from Louis Malle that recalls his memories of a Catholic boarding school in Nazi-occupied France. The unimaginable conclusion unfolds with nuance and restraint, but also a heavy undertone of guilt and regret.
7. Biutiful (2010)
Truth be told, I could have included a few films from just this past year on the list (Blue Valentine and Another Year were plenty depressing as well), but I decided to pick one, and it's Alejandro Gonzalez Innaritu's stiflingly unhappy Biutiful. The Job-like sufferings of Uxbal (played with devastating sincerity by Javier Bardem) get laid on thick and fast, almost to the point of excess. While the film reaches for poignancy with limited success, it'll succeed completely in bringing you down.
6. Rome, Open City (1945)
You could probably fill a list like this entirely with Italian neo-realist cinema, but while much revered classics like Paisan and The Bicycle Thief conclude with secretly hopeful denouements, Roberto Rossellini's Open City sticks in my mind as an irredeemably mournful elegy for Italy and its working class as it is torn open by WWII. The third act that sees three of our heroes held at the mercy of Nazi interrogators is at first unnerving, then riveting, and finally intensely sad.
5. No Country for Old Men (2007)
As previously argued on this blog, the Coen brothers' hopelessly dire No Country for Old Men is the most entertainingly depressing film of the decade. The entertainment stems from the Coens' quietly exciting storytelling technique, but the depression comes from the story that they tell; a bleak morality tale about good people fighting a losing battle against the implacable forces of violence and chaos. The ambiguous ending perfectly drives home that crushing sensation of futility.
4. Love Story (1970)
Tragic love affairs are not all that uncommon on the cinematic landscape. Some of them (especially of the musical variety) are among my favourites, but are remembered mostly for their moments of joy and unbridled romance than their weepy finales. Not so Arthur Hiller's 1970 melodrama, the lingering mood of which is a sombre one. In spite of its oft-quoted (and completely false) axiom about love and not having to say you're sorry, for me, Love Story is a splash of cold water in the face of Hollywood romanticism.
3. Das Boot (1982)
Arguably the best World War movie told from the German perspective, Wolfgang Peterson's claustrophobic saga spends three hours familiarizing us with the intricate workings of a German U-boat and its crew, but only to set us up for an emotional gut-punch at the end, one that speaks to the pointlessness of war and the insignificance of your effort if you're on the losing side. It would make an interesting companion piece with the similarly disheartening Vietnam War pictures made around the same time.
2. Waterloo Bridge (1940)
Each scene of this romantic melodrama carries a pang of sadness. That's because we know how the movie will end right from the beginning, and Mervyn Le Roy takes care to remind us of that throughout the picture with foreshadowing dialogue and Herbert Stothart's lovely orchestrations of the theme from Swan Lake. Vivien Leigh gives a heartrending performance (possibly her finest work), and Robert Taylor is appropriately dashing as the naïve man in love. Always makes me misty.
1. Grave of the Fireflies (1988)
Isoa Takahata's anime masterpiece is a sensitive but devastating expose of the effects of war not often seen in mainstream film, let alone animation, focusing on two innocent victims in Japan during WWII. The heart of this film is in the fleeting but earnest joy that the orphaned boy finds for his sister in the simplest of things, trying his best to keep the hardships of their war-torn existence from affecting her the way they affect him. This juxtaposition of the children's happiness against our grim foreknowledge of what's to come makes this as harrowing as any live-action war film you can name. It's a deceptive type of grief that sneaks up on you and slowly seeps in over the course of the film, leaving you so emotionally drained by the end that even to cry doesn't quite seem adequate enough.
