Top Five Saddest Films of All Time
#5: “Marriage Story”. This is the only film in my top five that isn’t based, in some fashion, on a true story, though it is painfully relatable. It’s a story about a divorcing couple and their pained attempts at maintaining their friendship, and as it makes my personal top five, it should spoil nothing to say that relations get considerably strained. The climax of the film has been memed considerably, but this film had brought me to tears several times before then and that climax hurts to watch; if you found that moment unrealistic, I envy you because that means you’ve never seen that happen in real life and I assure you it happens in real life.
#4: “Fruitvale Station”. This is a semi-biographical film chronicling the last day in the life of Oscar Grant, who died after being shot by a police officer under conditions that, to put it mildly, did not warrant Grant being shot. It’s the sort of material that could have been milked for award-baiting shlock, but director Ryan Coogler opts for a surprisingly simple approach, allowing the audience to get to know Grant (played by Michael B. Jordan) and grow to like the guy before ramping up to the gut punch of its climax. Easily the saddest film of the past decade.
#3: “Dear Zachary: A Letter to a Son About His Father”. This is the only documentary on my list and the only thing keeping it this low is that the top two are basically untouchable. Following the murder of Andrew Bagby at the hands of his ex, his childhood friend and frequent filmmaking partner, Kurt Kuenne, turns to interviewing friends and family so Bagby’s child, Zachary, can know what his father was like. Kuenne’s goal changes, however, when the ex, who is also Zachary’s mother, causes hell for Bagby’s surviving parents through legal shenanigans, and that’s about as far as a responsible synopsis can go because that’s when STUFF GOES DOWN. If you want to be in the mood to punch everything, watch this documentary. If you are a parent, have something on hand to calm your nerves before watching this documentary because you’re going to need it.
#2: “The Diving Bell and the Butterfly”. This is a biographical drama based on the memoir of the same name written by Jean-Dominique Bauby, a journalist who suffered a stroke that left him with a form of locked-in syndrome, rendering him mentally fit but unable to move any part of his body save his left eye. You might read that description and think, “Gee, that doesn’t sound like a fun movie to watch,” and you’re right! It isn’t! It’s terribly wrenching! There’s one scene where he tries to have a phone conversation and it’s the second-saddest thing I’ve ever seen in a film! The film eventually threads the needle to being aspirational, but this is about as sad as live-action films get.
#1: “Grave of the Fireflies”. This is an anime adaptation of a semi-biographical short story of the same name, about siblings who try to survive in the Japanese countryside during the final days of World War II. Basically, take every story you’ve ever experienced about kids living on their own and throw all of them in the bin because “Fireflies” is a million times more heartbreaking than all of them combined will ever be, climaxing with the saddest goddamn thing I’ve ever seen in any media, ever. There’s an English dub, but it can’t hope to capture the magic of the original Japanese voiceovers considering the young sister is portrayed by an actress roughly the same age as the character and some of the most powerful moments in the film(/the history of cinema) are greatly informed by that creative decision.
Adapted from a Facebook post dated November 2020, edited for context and language.