Just a nitpick, but Robin Wilson sings it. He’s still alive. It was the songwriter/lead guitarist, Doug Hopkins, who killed himself (he had issues with depressions and alcoholism and was kicked out of the band).
I Hate Everyone by Go Set Go. I song full of bile* for when you’re in a really foul mood. NSFW lyrics.
- Like the title didn’t give you a clue or anything.
I’ve heard that song a million thymes and have never really heard the lyrics. What a strange song. But then, Paul Simon…
ETA: I always thought it was Scarborough Affair.
Well, it’s not really Paul Simon’s fault lyrically – it’s a traditional English ballad, dating back to at least the 19th century (in various forms), with the thematic idea going even farther back.
How about Mac Davis’ Baby Don’t Get Hooked On Me?
The songhit #1 in 1972 with such touching lyrics as:
The revolver clicked, but did it go off? Dylan was a master at letting us fill in the blanks in his stories. I liked Senor for the same reason, we don’t know 100% of the story, and that’s fine.
Manipulative, perhaps. But whoever sings it is saying, “You broke my heart, and my love is gone. If you want it back… well, then you have to do some impossible things.”
Yep. The “Canticle” lyrics being sung “behind” the main theme are Simon’s, but they’re anti-war imagery and not what the poster was referring to.
Rolling Stones, “Midnight Rambler”
Frank Zappa, “The Illinois Enema Bandit”
Oh, good point. Somehow, I always seem to forget about “Canticle” that is sung under it starting with the second verse.
I think that was a trademark of Steely Dan…the first time I realized what “Everyone’s Gone to the Movies” was really about was, wait, is he a…?
I read somewhere that Jagger said he couldn’t or wouldn’t write the lyrics to “Brown Sugar” again…pretty nasty stuff…
There’s also “Via Chicago” by Wilco. The first few lines are:
"I dreamed about killing you again last night
and it felt alright to me.
Dying on the banks of Embarcodero skies
I sat and watched you bleed
I buried you alive in a fireworks display
Raining down on me"
Counting Crows have a song called “You Can’t Count on Me.” Sample lyrics:
“I got you down in your knees again
You watch the sky
It’s a pale parade of passing clouds that cover
The bed upon which we laid in the dark, and
The memories that I made of a laughing girl
But you’re just my toy, and
I can’t stop playing with you, baby”
Nope, no “you broke my heart” in it at all, just a old love affair that might have ended for any reason, but the singer (whoever it is–did I mention Paul Simon? Did the OP ask for singers, or songs and their protagonists?-- as I thought I made clear) is the one demanding an impossible ransom for its resurrection, which is cruel no matter who does it. The age of the song merely underscores the misogyny involved, but even in the rare female artist covers, usually singing the original version, the (female) protagonist does not come across as a nice person.
That’s the first one I thought of. At least he’s not explicitly anything more than a womanizer. The real problem is Dion’s other song, “Runaround Sue” describes the exact same behavior as if it’s unforgivable cruelty.
In an interview, maybe 5 years ago, Keith Richards told Terry Gross that the words of Under My Thumb might be wishful thinking, sung by someone who is actually under another’s thumb.
An oldie but a goodie: Patches by Dickie Lee. He loves a poor girl, Daddy says no, you can’gt marry her, she kills herself, and he plans to do the same.
I can’t begin to tell you what’s wrong with that story.
But now I’ll partly contradict myself (in having said songs mean what they mean to the listener) and say that seems to me to be directed at parents by a grown up recalling his youth, and that’s what the writer says it’s about. Not to say you can’t apply it to a love affair. 
Assuming it is about an adult looking back on teenage years, teenage kids are often dicks to their parents, true (IME around 2/3’s, one definitely, two partly ). And then you do forgive them (as well as realize you made mistakes with them too).
The Night the Lights Went Out in Georgia. What a piece of work that song it.
Sister kills her cheating sister in law and (one of) the SIL’s boyfriends, and lets brother get executed for it, with apparently no guilty feelings. Unless, her whole plan was to get rid of the lot of them? Then that’s even dickish-er.
Schrodinger’s cake?