Holiday Halfway, put out by various NFL teams around 1969, would be up there. Someone recorded a bunch of standard pop-orchestra backgrounds to a bunch of Christmas standards, and got football teams to have their players sing along (at very slow speeds to make sure they could keep up). I have the NY Jets and NY Giants versions, and they reek.
My parents bought it when I was a kid and my sister and I played it to death. About 5 years ago I bought a copy on EBay (yes I paid stupid money for it) just so I could surprise my sister with it.
It truly is awful. My wife won’t let me play it when she’s in the house.
So bad, that when I played it in the music store I worked in, I had several customers come racing to the register to find out what album that was, so that they could buy it and torture someone with it.
Probably not the worst (not counting all the gimmick records listed, it would be hard to outdo Bob Dylan’s album for pure shittiness), but the most recent PoS I’ve heard was the Justin Bieber Christmas record. It’s almost bafflingly horrible to my ears. I understand he grew up on top 40 crap from the 2000s, for which I pity him, but goddamn is that ever some soulless corporate crap. That “Mistletoe” song almost makes me laugh, it’s so moronic.
This album is particularly fun if you have cats. I bought it awhile ago to see what my cats thought of it, and it freaked them the hell out. Half of them just sat there staring glassy-eyed at the speaker while the others ran for the hills.
I don’t play it anymore. I love my cats, and I think this album qualifies as cruelty to animals.
I was in Best Buy several Christmases ago and one of his songs was playing over the PA. I told the cashier I was very sorry he had to listen to that. He said “Yeah, I don’t get paid enough for this!”
I have some Christmas CDs that have awful songs on them (The Three Tenors sing Feliz Navidad, anyone?) but I don’t think I have any CDs that are awful from start to finish.