It's odd, how some songs sound so beautiful, but when you listen to the actual words, they're incredibly sad.
Here's one: "Too Many Times" by Earl Thomas Conley and Anita Pointer.
The song is all about regret--a son who'd hurt his late father, a woman who abandoned her lover and misses him, etc.
And here's "Picture Postcards from LA" by Joshua Kadison.
Rachel the waitress dreams of going to Hollywood to be an actress or singer, but she always recoils at the last minute, even when she's got her bag packed and a bus ticket. It's become so routine all her co-workers, even the protagonist of the song who seems to love her, joke about it.
"In the Living Years" by Mike and the Mechanics.
A man doesn't get along with his father due to their differing opinions on unnamed issues (the video makes it sound like something to do with war, given how the son looks at a picture of his father in a military uniform) and not being able to understand the other's opinion. They never reconcile. To the point he isn't there when his father dies, something he regrets. Hell, of the three songs, this is the saddest one of all.
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