“Luau Cha Cha Cha” by Annette Funicello (not quite as horrible, but awfully kitschy)
Nowadays I would also include:
“It Ain’t Me, Babe” by Johnny Cash – great song but Cash fails miserably in his attempt to interpret it. Then there’s that female harmony, just to make things a bit more surreal.
Dave Barry’s original articles and book bemoan the fact that some songs aren’t well known enough to be widely hated. In particular, he points out a song called “Hooty Sapperticker” by Barbara and the Boys, which is a truly appalling song.
Since then, however, I’ve found one that’s even worse, although it may be disqualified as a “novelty” song: “I’m Gonna Spend My Christmas With A Dalek” by The Go Gos (not Belinda Carlisle and her bunch, it’s some earlier English pop band).
Yep, that’s what I came here to nominate. But another poster mentioned Having My Baby by Paul Anka, and I’d have to say those two would be neck and neck.
Having managed to forget about this song, I came in to mention Madonna’s cover of “American Pie”. You win the thread though…here, have a palate cleanser (animation of a Patton Oswalt routine - NSFW!)
“Muskrat Love” by the Captain & Tennille. Granted, there was plenty of terrible stuff put out in the '70’s, but this takes the cake for sheer awfulness. What do I win?
I was a freshman in high school when this song came out. I heard about it from a close friend who told me about how hilariously bad it was, and after I heard it myself I remember the two of us having a great time mocking it. How stupidly bad does your song have to be if 9th grade boys thingk it’s unintentionally funny?
But I don’t think it’s among the all time worst of the worst. Charlene could sort of sing OK, and musically there’s certainly worse out there. (Not lyrically, though- the lyrics are the dumbest of all time.)
No, the songs that make me want to dig my eardrums out with the nearest fork are “Shattered” by the Rolling Stones, “Everybody Must Get Stoned” by Bob Dylan, and “The Lion Sleeps Tonight” by The Pieces of Shit. Those songs grate on me like few other sounds this side of Hell do.