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The 9 Most Devastatingly Sad Documentaries of All Time

By Dustin Rowles | Lists | August 15, 2011 |

By Dustin Rowles | Lists | August 15, 2011 |

9. The Cove: Psihoyos and Barry assemble a crack team like some sort of Clooney to infiltrate and record the goings-on. They gather world champion free divers to plant underwater cameras and microphones. They get Industrial Light and Magic to craft hidden HD cameras in realistic boulders and shrubbery. They get high-tech night vision and heat-sensitive cameras to scope out for guards and danger as they go all Spy Tech on the fishermen. It’s a tense and dangerous operation because they’re going espionage on a multi-million dollar industry. Water park dolphins sell for a minimum $150,000. But their efforts work. We see the butchery first-hand, and it’s unnerving. Essentially, the dolphins are harpooned to death, as the cove fills with blood. By the finish, they’re hooking carcasses out of the water, and the cove itself is drenched with sanguine waters.

8. Grizzly Man: Your view on whether Werner Herzog’s Grizzly Man is devastating or not may depend on your opinion of Timothy Treadwell, who is either a goofball who got what he deserved or a idealistic animal lover who became a tragic casualty of nature and a bear’s instinct to kill. In either respect, Herzog allows the viewer to come to that conclusion himself. Grizzly Man is chilling, engrossing and provocative, and from my point of view at least, Timothy Treadwell was a sad figure whose desperation for love cost him his life.

7. The Times of Harvey Milk: If you thought the feature film based on the life of Harvey Milk was devastating, this documentary is sadder still, as it focuses on the real Harvey Milk, his inspirational political life, his valiant (and often successful) fight for gay rights, and his differences with Dan White, who eventually takes the life of Milk. That is where tears of sadness turn to tears of indignation, as White is spared a heavy sentence in part because the jury found the act was not premeditated, despite the fact that Dan White carried a gun with 10 extra rounds and avoided security on the day of the shooting.

6. Silverlake Life: The View from Here: Silverlake is Tom Joslin’s 1993 video diary of he and his lover Mark Massi’s experiences in the year following their diagnosis of AIDS. The deeply emotionally affecting film takes an unsentimental look at the way in which AIDS takes a ravaging physical toll on the body, but more than that, it’s a tragic romance about two men facing death together.

5. How to Die in Oregon: As much potential as this film has for being emotionally manipulative, it mostly avoids the almost expected gut-punches usually associated with “serious” documentaries. Pathos abounds, but it never feels manufactured; the people in the stories come off as whole, with as much humor as there is black despair and pain. As much as How To Die In Oregon could have been a political or philosophical diatribe, Richardson takes the harder route with minimal editorialization or sensationalism, and just lets these people be. And what they are is sad, real, and still questioning why death is never easy. It can only be eased.

4. Restrepo: Heatherington and Junger follow the platoon from deployment. So we get to see the boys in the shit, fooling around, and getting fired on. It’s horrible and hilarious, touching on so many levels. These guys are soldiers. These are boys, these are men with families who risk getting killed every day, these are swinging-dick meatheads who make gay jokes and hoot and holler as they blast away with artillery. These guys wrestle and throw dance parties. They blow a guy apart with heavy machine guns and high-five each other when they destroy him. These guys cry hysterically when they find the body of a fallen friend. They fight on, because as he lays there bleeding, Taliban rebels are still gunning down on them. They don’t win, they don’t save the world. Those that survived go home. And leave OP Restrepo to the next batch of grunts.

3. My Flesh and Blood: Part inspirational, part heartrending, Jonathan Karsh’s documentary follows Susan Tom, a super-mom who adopted 11 kids, all with - -mostly major — disabilities. It’s essentially a treatise on selflessness; somehow, the woman is able to devote, voluntarily and mostly complaint free, her entire life to the care of these children. The doc focuses not just on the remarkable woman, but takes an emotionally heartbreaking look at many of the children in her care, and the death of one in particular is almost too much to bear, particularly given the suddenness.

2. Senna: By focusing on the real-life drama, the intense rivalry, the backroom politics, the life-and-death stakes of those races, and the effect they had on the people of Brazil, Kapadia manages to relate the themes and ideas to anyone that has an interest in compelling stories about remarkable people. Not that Senna was a particularly compelling person in the humanitarian sense, but he is a fascinating person for how he approached racing. He was an aggressive driver, a man who often put winning ahead of his own safety and that of the other drivers, so sure of himself that his ability and his religion would save him from disaster. He took losses hard, and even when he was winning, he rarely looked exuberant. There was something sad and foreboding about Senna, and even if you aren’t familiar with the story of his life, you’ll feel an ominous sense of what is coming. Even still, when it happens, it doesn’t make that ache in the pit of your stomach any less gnawing.

1. Dear Zachary: Dear Zachary is one messed-up motherfucking documentary, people. And the less you know about it, perhaps, the better. Or maybe not. I knew nothing about it going in, and made the mistake of forcing Mrs. Pajiba-hyphenate to watch it with me. Within 11 minutes, she was sobbing, begging me to turn it off. Before I could find the remote, however, she’d been sucked back into an all-too engrossing story of a man’s freakish, tragic murder. But by minute 32, Mrs. Pajiba-hyphenate was inconsolable but transfixed, watching the next 45 minutes of the documentary with bleary, tear-filled eyes. Before the documentary ended, those tears turned to silent shock. And, for the both of us, it was perhaps the first time we’d ever been completely paralyzed by a film. It is an experience unlike almost any other, and your emotions will run the gamut, from sadness, to pride, to despair, to anger, to ache, and to complete disbelief, and unbelievable, mess-you-the-fuck up shock.