Jerkish characters (beginning with The Beatles) in songs

That is absolutely true, and definitely applies to “I Saw her Standing There,” which genuinely sounds like its from the POV of a teenage boy experiencing his first crush.

“You’re Sixteen” sounds like its from the POV of a middle aged guy who is absolutely stoked to be dating a sixteen year-old.

The Who have some lowlife characters in their catalogue, yet none more despicable than “Uncle Ernie” from “Tommy”

Entwistle wrote “Fiddle About” and was lead vocal on the original album, while Keith Moon wrote “Tommy’s Holiday Camp” though Townshend oddly sings vocals.

The perfect person to play Uncle Ernie is your drummer and Moon performs both songs in the movie.

I really love the Violent Femmes, and I trust that IRL they are nice people, but they have some really messed up songs, especially in their earlier work.

Country Death Song is about a guy who murders his child for no particular reason, then hangs himself.

Sweet Misery Blues is about a guy stalking and harassing a girl he likes: “Yeah, I’m gonna corner you in an elevator. Then you won’t be able to put me off till later.”

Mother of a Girl: “The way that I treated her was totally a disgrace. I wanted to permanently wipe that smile off her face.”

Keith Moon had the idea for the song, but Townshend wrote it and had it credited to Moon. IIRC he was afraid of what Moon would come up with.

Of course, Moon plays Uncle Ernie in the film version and turns the character into a weird comic relief bit.

Dixie Chicks…Goodbye Earl

They planned and carried out a murder, sunk Earl in the lake.
They had a good reason, but the law wouldn’t think that’s a still the thing to do.

Queen Bohemian Rhapsody “Mama, just killed a man…put a gun to his head, pulled a trigger and he’s dead”

Hey, come on. When you got right down to it, Earl was a missing person who nobody missed at all.

Yeah, he needed to die. :wink:

Was this guy in Reno at the time? Did the singer kill him just to watch him die?

Paul McCartney was barely 20 when he wrote “I Saw Her Standing There”.

Papa in “Papa Was a Rollin’ Stone” was pretty awful: a deadbeat dad who had three children outside his marriage, hustled people for money as a storefront preacher, would beg, borrow and steal to pay his bills. . .

The guy in “I Gotcha” by Joe Tex seems like an outright predator.

If we’re going with murder as a form of “jerkishness,” we got Springsteen’s character in “State Trooper” hoping said trooper doesn’t stop him on the road because he’ll (the character) will have to kill him (the trooper) because . . . well, for reasons having to do with something the character did. Very unsettling song.

Two fairly upbeat songs where the main character are fairly optimistically presented, but shot and/or killed innocent people.

Take the Money and Run by the Steve Miller Band

Billy Joe shot a man while robbing his castle
Bobbie Sue took the money and run

The Road Goes on Forever by Robert Earl Keen

Sherry drove the pickup through the alley on the side
Where a lawman tackled Sonny and was readin’ him his rights
She stepped out in the alley with a single-shot .410

Of course, later she let’s Sonny go the the electric chair for her crime.

Plenty of songs have murderers as characters, but both of these songs are often interpreted with their protagonists in a favorable light.

Cowboy Junkies’ “Black-Eyed Man” has the singer framing her lover for poisoning the town well…

Black-eyed man, he took the blame, for the poisoning of the well
They found his shoes by the pulley
They found his fingerprints all over the pail
With a noose around his neck, cicadas trilling everywhere
He says to the people gathered round him
‘It ain’t the water that’s not right around here’

…basically for not giving her the life he promised…

I always meant to say I’m sorry for the things I said and did
“Sorry”. I feel better now, do you?
But you promised me the sky and fell short a star or two
What else did you expect me to do?

Everyone’s Gone to the Movies by Steely Dan begins with:
Kids if you want some fun
Mr. Lapage is your man
He’s always laughing, having fun
Showing his films in the den

Come on, come on
Soon you will be eighteen
I think you know what I mean
Don’t tell your mama
Your daddy or mama
They’ll never know where you been

And so forth.

90% of Steely Dan material is about creeps and jerks.

Tom Jones - Delilah

At break of day when that man drove away, I was waiting
I crossed the street to her house and she opened the door
She stood there laughing
I felt the knife in my hand and she laughed no more

Or Miss Otis Regrets
Or Cell Block Tango

Or even a couple of old music-hall songs:

There was I, waiting at the church,
Waiting at the church,
Waiting at the church;
When I found he’d left me in the lurch,
Lor, how it did upset me!
All at once, he sent me round a note
Here’s the very note,
This is what he wrote:
“Can’t get away to marry you today,
My wife, won’t let me!”

And

Oh Oh Antonio he’s gone away
Left me alonio, all on my ownio
I want to meet him with his new sweetheart
Then up will go Antonio and his ice-cream cart.

I never really thought about it, but that interpretation makes sense. On the surface it seems like the narrator doesn’t want to get pulled over yet this particular fella has nothing to lose, so…

Lots of terrible people on Nebraska. From the title track:

I saw her standing on her front lawn
Just a-twirling her baton
Me and her went for a ride, sir
And ten innocent people died

And Johnny 99:

He came home too drunk from mixin’ Tanqueray and wine
He got a gun, shot a night clerk, now they call him Johnny 99

On Highway Patrolman, it’s the title character’s no good brother, Frank:

There was a kid lyin’ on the floor lookin’ bad
Bleedin’ hard from his head
There was a girl cryin’ at a table
And it was Frank, they said

Nebraska is one dark album.

Richard Thompson singing “I feel so good, I’m gonna break somebody’s heart tonight…” is a great portrait of a jerk.

Stagger Lee, on the other hand, is more a straight-up murderer than an insensitive twit.

Frank Zappa…take your pick. The emcee of “Wet T-Shirt Nite” comes to mind. (“Yes, that water is cold, kind of feels like an ice pick to the forehead. And now the ice pick to the forehead!”)

But why would you write “just seventeen,” implying she is young, if you’re singing from the persepective of another teenager?

Taylor Swift’s “no body, no crime” where the protagonist murders her friend’s killer.