The nominees:
1) Alanis Morrisette: "You Oughta Know"
No suspense here. The hardest part is figuring out what lyric is the most cringe-worthy, making you wish she'd written it on a napkin and then thrown it away rather than share this with the world. It's a three-way tie between "Is she perverted like me?/Would she go down on you in a theater?", "Does she know how you told me /You'd hold me until you died/Till you died, but you're still alive", and "And every time I scratch my nails/Down someone else's back I hope you feel it". Just as the happenings in the song "Ironic" are not ironic, blow jobs in movie theaters aren't really perverted. The second set of lyrics are classic to the genre---an embarrassing admission that you took a lover's exclamations of affection as if it was a ironclad contract. The third is just embarrassing, because the answer is clearly, "He can't feel it, and he obviously doesn't care."
2) The Supremes: "You Keep Me Hangin' On"
This one is hard to enter, because it's such a great song, unlike the first selection. But despite being a near-perfect pop song, the narrator seems to be unaware that women are permitted to dump men. Example:
You say although we broke up
You still wanna be just friends
But how can we still be friends
When seeing you only breaks my heart again
And there ain't nothing I can do about it
We've all seen or been in this situation, but it's hard to escape wanting to tell the narrator, "There is something you can do about it. Quit answering his phone calls, to start with."
3) ABBA: "Take A Chance On Me"
The chorus says it all:
If you change your mind, I'm the first in line
Honey I'm still free
Take a chance on me
If you need me, let me know, gonna be around
If you've got no place to go, if you're feeling down
If you're all alone when the pretty birds have flown
Honey I'm still free
Because desperation put to disco is suddenly alluring.
4) Beyonce: "Single Ladies (Put A Ring On It)
This song is in the "You Oughta Know" region, because just like the first song on this list, it packages lyrics that scream low self-esteem as if it was some kind of feminist anthem. But in reality, it's cringe-worthy, with the narrator's clinginess and desperation shining through: "Don’t be mad once you see that he want it/If you liked it then you shoulda put a ring on it ".
Look, if you actually get the nerve to say that to a guy, he's probably not going to be jealous so much as think that you're sure clingy that even when you're hanging on other guys, it's about getting that damn diamond ring from him.
5) The Clash: "Train In Vain"
Same problem with "You Keep Me Hangin' On", which is that this is a great song, and it just begs you to sing along. Which is dangerous, because you'll get into and realize you're singing this:
Say you stand by your man
Tell me something I dont understand
You said you love me and thats a fact
Then you left me, said you felt trapped....
You must explain why this must be
Did you lie when you spoke to me?
The "opt-out" clause in sweet nothings is understood. Maybe we forget it during the height of a break-up, but that's when you cry it into a pillow. This song exposes the douchebag within, which makes it pretty hard to bear.
Here's the poll:
Leave your reasons for your choice in comments, and nominate songs I didn't think of, if you'd like.
Malcolm Gladwell 
(Sorry for the brief hiatus - I was teaching all weekend. Whee!)
Very cool: 
Catching up on my blog reading, I read 
A blogger
Okay, Broadsheet has another example of what might be my least favorite trend story of all time: