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Tear Jerker: Dead Rising
Dead Rising pits you against many psychopaths as the game progresses. Most of them are just normal people who snapped and went crazy when the zombies arrived, and the player must kill them to protect other survivors. One of them is a crazed Vietnam veteran carrying a machete, who wanders around in a hardware store. Only after fighting and nearly killing him does he reveal that he has been suffering from flashbacks to Vietnam the entire time. While this was obvious to most players, what he revealed next came as a shock: He had been out on a shopping trip with his young granddaughter when the zombies arrived, and he watched as she was torn apart and eaten by zombies. He tells you this as he hands you his wallet with a bloodstained photo of his family. After his granddaughter died, his vision "flashed white" and he starting suffering from flashbacks. He tells you this after you, the player, have just ensured his death.
Ending A, watching Frank fall down in defeat at the Helipad while he gets swarmed by zombies...thank God for Overtime
No wait, forget Overtime, that ending is worse because it seems Isabella and Frank are both completely screwed. This troper hasn't played Case West yet, so hopefully Isabella will be safe...
Nope. Not only does it turn out that Isabella made a deal with the devil with Phenotrans by giving them the antidote recipe and was unable to give out the permanent cure, she was unceremoniously kidnapped under the Phenotrans CEO's orders.
Cliff's death scene. Nngh. Either Carlito's death or, more likely, as it doesn't include his Eagleland Type 2 preaching, (Isabela's reaction to it may count for some as well.)