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Tear Jerker: Dead Rising 2
Dead Rising 2 charges you with making sure you maintain a daily supply of Zombrex to keep Katey, Chuck's infected daughter, from turning into a zombie. Should you fail in this, the game's story missions become locked out. When you return to the safehouse in anticipation of the military's arrival, however, the sheer weight of Katey's death makes Chuck suffer a Heroic BSOD as zombies breach the safehouse. With Katey dead, and with no reason to go on anymore, he does nothing as the zombies pull him to the ground and devour him. There's a reason this ending is graded "F".
Made worse by Off the Record: Katey apparently died and Chuck went insane, becoming a psychopath thinking a doll was his dead daughter. Watch this and tell me like you didn't feel like crying.
Frank's double Lampshade Hanging after the fact may have been intended to break the tension, but it might just make everything worse depending on how much of a Chuck fan you are.
In Off The Record, if you visit the Green Room during the initial outbreak (which is where Katey was hiding in the original), you'll see that her backpack is on the ground with smears of blood near it. That is just straight up depressing.
Oddly enough, Sullivan's death in Off The Record.
Frank: Thanks for saving my ass Sullivan. You were a good man.
Also from the aftermath of that same scene, if you examine Rebecca's body:
Frank: You could have been great, kid... We could have been great...