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Dark Era gives enough reasons to cry a river:
The photo made at the start becomes Harsher in Hindsight when Ango realizes that he probably will never see them again. Although he later meets Dazai again, but the context is far from friendly.
Continuing on that, this line from Dazai when asked why they should take a photo. Oh, Dazai...
Dazai: Because I feel like, if we don't do it now, there won't be any evidence of our continuous presence here in the first place.
The scream at the end of Episode 15 Oda gives when he loses everything.
Oda: Suddenly, I hear someone screaming. Then I realize that I am the one screaming due to my throat being dry...
The last Buraiha meetup. This scene is tragic because of a couple of reasons: 1) Up to then, Ango still had hope that they would stay friends even when times get rough, and it worsens when Odasaku says that it's impossible. 2) This is the last meeting between Ango and Odasaku before the latter dies, so there is no reconciliation.
In the season 3 ending, Dazai confronts Fyodor again, smiling all smug as Fitzgerald reveals to have tracked him down with the Eyes of God. However, when Ango arrives, this smile immediately dies down.
We see Dazai trying desperately to reach out to Odasaku by reminding him of the ideals he once had only for him to be rewarded by his former friend walking away to his death.
More about this particular scene. Odasaku runs away during Dazai's breakdown. It's partly because he wants to find Mimic and partly because he is freaked out by Dazai's words and how they're coming from The Stoic of the cast. This leads to Dazai begging for Odasaku to come back.
Episode 16 makes the peppy ending theme, "Kaze Ga Fuku Machi" note Town Where The Wind Blows a tearjerker...Take a look at the lyrics, and you realize that the song is all about Dazai and his resolve to fulfill the promise he made to a dying Oda.
A very subtle example occurred in April 2019, on the Japanese version of BSD's smartphone game Mayoi. On April Fools' day, every character in the game turned into kids or a kindergarten teacher, and so did the Buraiha trio...
The ending of the Dark Era is even worse in the stageplay.
Good news, the bar where the trio met up really exists (Lupin at Ginza, Tokyo). Now you can go there yourself and relive the sadness! The best thing? There is a shelf with the books of the authors who frequented the bar. Among them are two copies of the Dark Era Light Novel.
It has been confirmed that in every timeline/universe, Oda will die and he is not to be saved. When Dazai rewrites The Book to circumvent this, it results in Oda not even being his friend. Really makes you think...
Then we have a Light Novel set in a universe where Oda lives! ...Because he was never Dazai's friend, to begin with.
Notice the place where Odasaku is buried in Dead Apple. It's placed higher than the other graves, overlooking the sea. What was his wish again?
Despite its cheerful and lighthearted tune, Dazai's character song has some really depressing lyrics, which fit his character perfectly. Not to mention, these lines, which are, without any doubt, dedicated to Odasaku:
" Days darkening in the setting sun are endless. In a world like that… I found you. Suddenly, that hand pulls and stops the cuff of my reckless heart."
The entirety of chapter 40/episode 18. Fyodor meets a boy who is a slave of Ace, a mafia executive with the power to convert his subordinate's lifespan into gemstones. The boy shares some of his deepest desires with Fyodor, who acts kind to the boy. He curses his powerlessness and one day wishes to overthrow the mafia and even fantasizes about it. Fyodor drives Ace into madness, which leads to the executive performing suicide. But because the boy was a witness, Fyodor kills him.
Despite him only appearing in one chapter/episode, we know quite a lot about this boy. He became a slave of Ace before he could even walk and has to wear a gem-encrusted collar for the rest of his life. This was fertile ground for his contempt for Ace to grow on, and he is confident that Fyodor will be his way to salvation because he hopes that Fyodor will kill Ace. He's entirely devoted to his dream, believing that one day he will escape. But it's exactly because we know a lot about him that his situation becomes very tragic; in the end, he doesn't matter.
Regardless of how you feel about Atsushi dwelling on it, his Dark and Troubled Past is genuinely sad. Orphaned from infancy, raised in an Orphanage of Fear where he's abused and bullied by both kids and adults over mundane things, cursed and slapped around just for existing. Atsushi's gone through a lot of trauma, from constantly being told he's worthless and has no place in the world, being chained and locked in a dark cell, to having a nail hammered into his foot. You can't help but want to give him a hug.◊
Chapter 78 delivers one big gut punch, to say the least, about Kunikida's situation. He's lost both of his hands and is in the Hunting Dogs custody. Jouno decides to visit, only to mock him. Oh, and before he leaves, Jouno tells him that Yosono's execution is today before tossing Kunikida his torn notebook. THAT finally causes Kunikida to break down into tears.
Chuuya's backstory is this combined with a good helping of Nightmare Fuel. Originally, the military kidnapped a boy who couldn't have been older than seven and faked his death to prevent anyone from looking for him. He was then cloned, creating another Chuuya, who was modified and made to act as a vessel for Arahabaki. Rimbaud and Verlaine eventually showed up to capture him but disagreed about what to do with him. Despite being good friends, Verlaine could not allow the clone to be handed over to be experimented on and Verlaine betrayed his partner to save the boy. This resulted Arahabaki blowing up the facility and the surrounding area, allowing one of the Chuuyas to escape though he had no memory of his time there. He eventually joined the Sheep who used him as a weapon for a while before being tricked by Dazai into betraying Chuuya, who was extorted in joining the mafia. After that, he struggled with the fact that he did not even know if he was human, and when the friends he made in the Port Mafia tried to help him learn about his past, he found soon after the information they found for him was false and soon after they were killed by Verlaine. However, in the end, it's left up in the air as to whether or not Chuuya is the original or the clone, but he ultimately decides it doesn't matter.
If you add on the events of the Dragon's Head Conflict, Chuuya lost another group of friends less than a year later.
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