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Tear Jerker: Sam & Max
The end of Sam & Max: The Devil's Playhouse. Sam's slow, sad walk through the credits after Max's death is just depressing. Especially the part where he walks past a mugging without paying it any attention.
For me, the waterworks turned on in "crimefighting" ending, when Sam and Max start to excitedly discuss their next case, reunited again after briefly losing each other.