1) Baby, It's Cold Outside - I've linked to the Dean Martin recording because I really like it. I love this song, actually. It makes the list because IT'S NOT REALLY A CHRISTMAS SONG! See also: Let It Snow.
2) Jingle Bells - I've linked to a Sinatra rendition. Again, it's a good version of the song. It makes the list because Jingle Bells is not only not a Christmas Song, it's been done badly more times than anybody can count. Seriously, searching 'jingle bells' on YouTube yields over 87,000 results.
3) Over the River and Through the Woods - I've linked to Danny Kaye and the Andrews Sisters. I like this version because it's actually "Over the River and Through the Woods" not the verses of "Over the River" with Jingle Bells for the chorus (see above), but this song was written for Thanksgiving, and singing 'Merry Christmas' over and over at the end doesn't change that.
4) The Little Boy That Santa Claus Forgot - This is the Phyllis Robbins version, a somewhat less depressing version of the most depressing song ever. About a poor boy. Who "hasn't got a daddy." And Santa didn't bring him anything. Isn't this supposed to be the time for Good Cheer??
5) Santa Baby- Eartha Kitt. This one makes the list because she basically says, 'I wasn't slutty this year, so you should bring me a pony and a million dollars." Wow, that's a great way to look at things.
6) My Favorite Things - Coltrane. I love this version of the song. I look forward to hearing it at Christmas, actually. But guess what! Show tune! Not a Christmas song. You may remember it from a little show called "The Sound of Music" which was about Nazis and a nun who falls in love. And about a million kids, wearing clothes made out of the curtains.
7) Every loud, rock, or disco version of Silent Night - I picked the "We wish you a Metal Xmas" version because it illustrates my point perfectly. If I remember the story correctly 'Silent Night' was written by the pastor of a church who discovered that an animal had chewed a hole in the organ bellows. Meaning no music for Christmas Eve, therefore a SILENT NIGHT. It was written for acoustic guitar and solo voice. If you're doing this song loud, you missed the whole point.
8) Grandma Got Run Over by a Reindeer - because it's AWFUL!
9) The Man with All The Toys - I have a huge soft spot in my heart for the Beach Boys, I really do, but the harmony is a guy going "bop" at the end of every line. Really????
And last but certainly not least:
10) Christmas Without You - Dolly Parton and Kenny Rogers. Beautiful song, beautiful sentiment. Their voices are great together. But every time I hear the line "Christmas songs that we knew, and used to make love to" I want to throw up a little inside my own head. Nothing ruins a song like the mental image of Dolly Parton having sex to Christmas carols. Eeeewww!
These aren't necessarily bad songs. I've purposely including the versions that I like quite a bit for most of them. They're mostly just really bad at being Christmas songs, but nobody plays them except at Christmastime.