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Tear Jerker: Yu Gi Oh GX
Jaiden trapped in the mind of the Supreme King. The happy-go-lucky hero who's reaction to immensely powerful harbingers of doom and darkness have ranged from comedic to inspirational is trapped in a perpetual Despair Event Horizon where he's unaware of the horrible things the Supreme King is using his body to do, and where he can only wallow in self-loathing as he blames himself for his friends' apparent deaths.
The above entry is so traumatic for him that he spends almost the entirety of the final season as a cynical Hurting Hero. He rarely spends time with his friends, almost never smiles, only duels—his passion and most joy-inducing pastime—when doing so is absolutely necessary when it comes to saving the world.
The other Broken Ace, Ryou/Zane, was just as heartbreaking. Used to be respectful despite his stoic and aloof behavior, he finally snapped after a humiliating loss and willing to do anything to achieve victory even at the expense of his little brother. He gets better, but it's still sad to see the once respectable Kaiser bounded to a chair.
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