Six Feet Under.
I fucking bawl my eyes out each time.
If you know the format for that show then you know that each episode starts with a scene showing the death of someone and well in the ending it shows Claire driving up a highway on her own on the way to New York to start a new life with a new job and she plays the gorgeous song Breathe Me by Sia on her radio and so begins a sequence featuring the families future deaths. You watch how they all die in future years and its just horrible honestly. I mean its beautifully done, but when you've watched these characters for years on tv and you see how they will eventually die then it kinda fucking kills your heart. Ruth and Davids death are particularly painful because of who they see as they die and yeah wow I feel like crying just talking about it.