I was going to avoid this one…
but When She Loved Me from Toy Story 2,
and Coming Up Close by Til Tuesday. I thing a song about a relationship that failed is no where near as sad as for one that never even got started.
eta: why is “coming up” highlighted in blue, at least on my screen? eata: it did it again!
I saw Toy Story II once. Once.
Fast Car, by Tracy Chapman. Gets me every time.
I’m shocked, shocked I tell you, that nobody on this message board has mentioned “Honey.”
The preceding sentence is not to be taken seriously.
“Johnny Has Gone for a Soldier” covered by James Taylor and Mark O’Connor.
“Love Has No Pride” Linda Ronstadt covered this in the '70s, but the Bonnie Raitt version backed by Crosby, Stills and Nash destroys me every time.
“Danny Boy”.