Well there's a couple that make me cry for different reasons)
Main 3 though that I can name are
Dancing Crabs (from the Sims 2 Castaway ost) mostly because nostalgia and memories..
Home - Resonace mostly because some how it mostly makes me feel empty inside and sad at the same time in an indescribable way.
And Professor E. Gadd's lab theme from the GC Luigi's Mansion (although I'm listening to it rn and it's not making me sad at all somehow) due to same reason of the first but way in a more direct painful way because I'll never get to experience them ever again for reasons. (Some of which are quite personal..)
Edit: Came back here because I realized I mixed the 2nd one's title and song artist up.