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Tear Jerker: Rival Schools
Rival Schools 2 and its Bad Gedo High ending. It has Daigo dead, Akira breaking down in tears as she mourns him, and both Edge and Gan screaming and swearing revenge on Kurow...
The Taiyo High ending is just as bad, with Hyo's death in his brother Kyosuke's arms as he pleads him to not die, and then Kyosuke disappearing from Taiyo in despair.. It gets even worse when you remember that Hyo's seiyuu, Kaneto Shiozawa, had died before the game was finished.