The saddest video game music I've ever heard was during the water stages of Wario Land: Super Mario Land 3. Every time I hear that music it reminds me of a friend of mine leaving and me never seeing that friend again. One friend in particular was an intern teacher I met from another class when I went to middle school during the 1986/'87 semester. Early the next year she left and I never saw her again. When I hear that particular music it makes me miss her.