Top o’ the heap here indisputably belongs to “Sylvia’s Mother” by Doctor Hook and the Medicine Show. Mr. Creepy Loser Ex-BF is in tears by the end and never does get past mom to actually speak with Sylvia.
Second Place goes to “I Ain’t Missing You” by John Waite. The loser in this song is not only whiney, but is also doing a half-assed job, utterly unconvincing job of denying his loserhood.
I’m not in love, so don’t forget it
It’s just a silly phase I’m going through
And just because I call you up
Don’t get me wrong, don’t think you’ve got it made
/////
I keep your picture upon the wall
It hides a nasty stain that’s lyin’ there
So don’t you ask me to give it back
I know you know it doesn’t mean that much to me
Except that “Sylvia’s Mother” is a parody. The song is hilarious.
Warren Zevon’s “Poor Poor Pitiful Me” is about a whiner, but since his problem is that women throw themselves at him, I doubt he’d a loser.
There is Elton John’s “I Think I’m Gonna Kill Myself.” Not to make light of teen suicide, but killing yourself because you’re bored is pretty self-centered and whiny.
I nominate Gilbert O’Sullivan’s Alone Again (Naturally)
In a little while from now
If I’m not feeling any less sour
I promise myself to treat myself
And visit a nearby tower
And climbing to the top will throw myself off
In an effort to make it clear to who
Ever what it’s like when you’re shattered
Left standing in the lurch at a church
Where people saying: “My God, that’s tough
She’s stood him up”
No point in us remaining
We may as well go home
As I did on my own
Alone again, naturally
Here’s the thing, though. At the time, those tortured souls were sexy to me. Although, my stepmom said I used to have a bad case of “lost puppy syndrome” (Dating guys who strongly resembled sad, lost puppies)
Isn’t this the point of the Smiths and Morrissey’s entire discography? Some of my favorites from it are: “I Know It’s Over,” “Last Night I Dreamt,” “Heaven Knows I’m Miserable Now,” and “King Leer.”
Of course, the classic song bashing whiny types is the Eagles’ “Get Over It”
Yeah you drag it around like a ball and chain
You wallow in the guilt; you wallow in the pain
You wave it like a flag; you wear it like a crown
Got your mind in the gutter, bringing everybody down
You bitch about the present and blame it on the past
I’d like to find your inner child and kick its little ass