I’d also nominate the same band’s “Berlin Chair” - it’s more imagery than an obvious narrative, but the entire song is basically from the viewpoint of a guy who’s telling a girl who likes him that he’s a whining loser.
If she waits around he’ll give all his aches to her. He’s the rerun that she’ll always have to force herself to sit through. He likens himself to a sculpture that’s too fragile to serve as the furniture it’s named after.
But, if she really wants to, she can get involved with him and “lean on me 'til I break”.
The first time I heard it I assumed that I missed the “…but I love you and that makes it all O.K.” section. Nope. Just whining.
This kid is so whiny that, when he just turned two, he felt so betrayed by his parents (when they had a daughter) that he left home when he was 17, hoping “to find all the love that he had lost in that earlier time.”
Who knew that two year-olds had such delicate hearts and perfect memories!
Frank Sinatra / Billie Holliday’s “I’m a Fool to Want You” goes near the top of the list:
*Time and time again I said I’d leave you
Time and time again I went away
But then would come the time when I would need you
And once again these words I had to say
Wasn’t there a TAXI episode where Louis DePalma stood at a jukebox with a beer in hand playing it over and over (and singing to it) because he got dumped by his girlfriend?
No one knows what it’s like to be the bad man,
To be the sad man behind blue eyes.
No one knows what it’s like to be hated,
To be fated to telling only lies.
The Spin Doctors’ “Jimmy Olsen’s Blues” isn’t about a loser per se, but c’mon - Jimmy competing with Superman for Lois’ attention? At least when he tries to do something about it he goes armed with a pocket full of kryptonite.