Songs like Last Kiss?

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So my boss reintroduced me to an old favorite song: Last Kiss by Pearl Jam. She had forgotten the name and told me it was a depressing song and I immediately thought of it since I used to listen to the song and want to cry. And after listening to it again, the emotions it stirs are very real and powerful.

Have you heard the song and do you know of any other songs like it? Specifically about tragedy to an arpeggiated guitar riff but anything that you can feel the emotions of the singer.

Here's a couple. They aren't very similar musically, but they all focus on similar themes:

Here's another one from Pearl Jam: https://www.youtube.com/watch?v=E0JwW623n1A

A more subtle one by Simon and Garfunkel: https://www.youtube.com/watch?v=BPTOY8FrvNw

Another by Paul Simon (which you may recognize from Scarborough Fair): https://www.youtube.com/watch?v=Rirhs8O88hU

Here's one by James Taylor, that's probably the most similar thematically (all the more poignant in that it was about a close friend of his): https://www.youtube.com/watch?v=JOIo4lEpsPY

Those are fantastic songs and great suggestions. Thank you so much! I have Fire & Rain as well as Side of a Hill but forgot about them. The other two I haven't heard before. Thanks again!