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I don't remember the group who did it, but "Timothy" was pretty depressing. Three guys caught in a mine shaft cave in, Timothy, Hungry Bob and the singer. Timothy doesn't make it to the rescue, cannabalized by the other two. The guy who wrote the song, Rupert Holmes, also did "Escape (The Pina Colada Song)" as a solo a few years later.
Or, there's the Beatles "No Reply." A paean to stalking from the early 60's. I mean, get a clue here! She tells you she isn't interested in you anymore, her parents lie to your face on her behalf, and she hangs up when you call. "You are being served with this restraining order . . ."
How about "Bobby's Girl":
I wanna be Bobby's Girl
I wanna be Bobby's Girl
That's the MOST IMPORTANT THING TO ME
'Cause if I was Bobby's Girl
If I was Bobby's Girl
What a faithful, thankful girl I'd be.
As for Billy Joel's oeuvre, "Piano Man" is kind of depressing, but "Los Angelenos" and "The Entertainer" are pretty bleak, too.
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