I would probably pick Haneke’s “Benny’s Video”…
I always found Pierrot le fou to be both intensely beautiful and extremely tragic at the same time. I don’t think any other film has ever left with such a strong feeling of sadness after a viewing. And it does this every time I watch. I guess I’m a glutton for punishment, but it’s such an incredible film that I can’t help but go back to it.
“21 Grams”, “The Fire Within”. But you asked for one…“The Fire Within”.
Ingmar Bergman’s work tends to depress me a lot; Shame, Cries and Whispers, Winter Light, The Virgin Spring, and a few others.
I’ve also found Ikiru to be the most emotionally affecting Kurosawa film I’ve seen.
Vivre Sa Vie (since someone mentioned Godard) was depressing.
I found In Bruges to be depressing, but not in a hopeless blackhole kind of way (unlike Bergman’s work).
Others: Withnail and I, Woyzeck (Herzog’s version in particular), The Proposition, The Pledge.
Breaking the Waves
Open City ain’t no lollipop.
Todd Solondz’s HAPPINESS.
Capturing the Friedmans is pretty sad.
Lost in La Mancha – that depressed me at least.
Wet Hot American Summer
Don’t Look Now
Day of Wrath
in a year with 13 moons
sympathy for mr. vengeance
ikiru and red beard have some of the saddest moments i’ve seen in film, but as a whole they’re far from depressing.
Grave of the Fireflies and the Bicycle Thieves are both fairly downbeat throughout and they allow you to leave on a wave of depression thanks to their monstrously grim endings.
“Boys Don’t Cry”
“Million Dollar Baby”
All are films that are finely crafted in every department and I’ve tried to re-watch them but I just can’t.
A.I. was really depressing. the ending is just so sad :(
i also found Mean Creek to be really depressing.
ThinChildren of ParadisePierrot Le FouAu Revoir Les EnfantsPaper Covers RockIrreversibleHungerThe Elephant Man
& Tideland put me in a melancholy head-space, but I don’t think it is depressing in itself.
“Requiem for a Dream” and “The End of Evangelion.”
In a Year of 13 Moons
Dancer in the Dark (because of the last ten minutes and because you always think this does not have to happen), lots of Ingmar Bergman of course and with Fassbinder you can pick almost everything. I’d suggest In einem Jahr mit 13 Monden (In a Year with 13 Moons) or Angst essen Seele auf (Ali, Fear Eats Soul), his Sirk-Remake where neighbours, work mates and family are much more meaner than in What Heaven Allows .
Empire has a top 10 list of depressing movies with Requiem for a Dream on position 1.
oh i forgot umberto D
Begotten and 21 Grams.
They Shoot Horses, Don’t They?
Electra Glide in Blue
Johnny Got His Gun
One Flew Over the Cuckoo’s Nest
The Seventh Continent
Come and See
The War Zone
I Only Want You to Love Me
The Barbarian Invasions (Denys Arcand, 2003). Extremely depressing in that I wasted 100 min. watching this piece of crap.
Au Revoir Les Enfants because unlike so many other films (i’ve seen) that people have listed, there’s no hope at the end of this film. the tragedy isn’t made better by a reaffirmation of life, or some heroic sacrifice—its more realistic. it is what happened, and its haunted the memory of the filmmaker ever since, and its depressing because of the helplessness that you feel when you watch the ending. one of the saddest and most depressing films i’ve ever seen.
Elephant (Hated this movie, thought it was bullshitty, depressing nevertheless)
Grave of the Fireflies (Great film, one of the best animated films of all time)
Dancer In The Dark (Another good film, although I generally dislike Lars Von Trier. It might be because of my love toward Bjork)
Autumn Sonata never ceases to bum me out for a few days. And yeah, I agree that nearly all of Fassbinder’s films are quite depressing given his absurdly banal and down-right negative outlook on the world. I also found Satantango to be extremely depressing in the end.
It’s interesting though, these are some of my favorite films. I guess that says a lot about me.
Au hasard Balthazar
Grave of the Fireflies, but each time I watch it (nearly 10 times now) I find myself more and more touched by the spirit of the main characters.
@Pajamas I always cheer myself up with the fact that I also love Happy-Go-Lucky.
Eric Rohmer is always nice for cheering up too.