This is an odd one. There are several songs that make me sad for different reasons and in thinking through them, I tried to pick one that made me sad for nostalgic reasons as opposed to dark ones. The song that immediately came to mind was:
Lost for Words by Pink Floyd
This is certainly not a sad song, by any means. But the context for the song is nostalgically sad. The album on which the song appears, The Division Bell came out in 1994, the year I graduated from U. C. Riverside, and I remember listening to the album over and over during the spring semester of my senior year–my final quarter at college. Listening to the song reminds me of those long lost days at school when a career in the real world was little more than vapor and I was running on the successes I had built up over the previous few years, the long hours I put into my studies, the longer hours I put into my job in the dorm cafeteria. Especially, the song reminds me of wandering one final time across the campus on an early morning, with the sun rising in the east casting long, dark shadows over the ivied buildings. Those were good times, innocent times when the notion of a family and a job and all of that responsibility was an idea far in the future. They were times shared with good friends. And whenever I hear “Lost for Words” it reminds me of those now long lost times.