Not sad as in "that was unfortunate/stupid" but sad as in tearjerker-moment sad.
Given their background stories and method in which they died I would probably pick (in no particular order)
Naruto's parents (specifically Kushina), Haku, and Nagato
Given their background stories and method in which they died I would probably pick (in no particular order)
Naruto's parents (specifically Kushina), Haku, and Nagato
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