Gaara, naruto, and sasuke, when showing flashbacks of they childhood straight up f**king sad, A FATHER WHO WANTED YOU DEAD, A ENTIRE VILLAGE LOOK AT YOU WITH SUCH NASTY EYES AND SEEN YOUR ENTIRE CLAN FALL DOWN TO A HAND FULL, sad indeed
Kakashi or tsunade. Kakashi because everyone he loved died. And tsunade because she was supposed to be a world known medical ninja but she couldn't save her loved ones. And they both had long term effects.
-Obito when he saw Kakashi Raikiri Rin
-Konan last moment before she died
-Guy when he want to open 8 gate. That he know this is his last moment or to be precisely Youth moment before he die.
-Zabuza last moment with Haku.
-Minato and Kushina final moment
-Itachi last moment before he going vanish after edo tensei release