Goin’ on a Date with Santa* as sung by Dr. Elmo (of “Grandma Got Run Over by a Reindeer” fame).
*small PDF
Different sort of creepy: “Zat You Santa Claus” as performed by Louis Armstrong.
In the animated show “Santa Claus is Coming to Town” Kris Kringle sings a song called “A Kiss A Toy” with the lyrics (courtesy of The Bradford Exchange – Limited Edition Collectibles, Figurines, Jewelry And More):
I know what he means but it has always creeped me out!
“Baby, It’s Cold Outside,” flipped to either make it creepier or, if you are a male geek, immeasurably hotter.
She’s continuing her history of questionable judgment. 
Creepy Christmas songs?
Grandma Got Run Over By a Reindeer, of course.
Let’s face it: Grandpa offed the old lady and is blaming it on St. Nick. And bringing his grandchild into the fiction! Bastard!
Song’s not so creepy, but the accompanying cartoon is: Suzy Snowflake. A Chicago TV tradition for decades, it was being played on WGN’s Bozo Christmas specials well into the 1990s, and an ex-girlfriend from the Pittsburgh area tells me it was a tradition there as well.
Also a tradition in Chicago was this other creepy song/cartoon, Hardrock, Coco, and Joe.
shellofmyformerself, please don’t post more than a small sampling of lyrics; link to the full version elsewhere. (Your link didn’t work for me, BTW.)
Thanks,
twickster, Cafe Society moderator
I can’t find the lyrics on-line, but I Don’t Remember Christmas is creepy.
The singer lists about 97 things not remembered about a past relationship.
I don’t remember sprintime
I do not remember fall.
So it’s possible December
Never happend after all.
Did we trim the tree together?
I can’t get the image through.
Cause I don’t remember Christmas,
And I don’t remember you.
The impression I had is that the guy is heartbroken and trying to make himself forget the memories of his lost love. Or he has dementia. Or something.
Not that it creeps me out particularly, but Rudolph the Red-Nosed Reindeer has always pissed me off. All of Rudolf’s playmates ostracized and teased him unmercifully because he looked different, but sang a different tune once he demonstrated that his genetic abnormality actually had some utility in pulling Santa’s nuts out of the fire. If I had been Rudolf and Santa asked me, “Rudolph with your nose so bright, won’t you guide my sleigh tonight,” my response would have been “Bite me.” I would have been one bitter reindeer.
I’m only half joking.
Why is it creepy? I actually quite like it!
You’re right about that. That’s why I (sort of) hate the Rankin Bass one. I mean, I love it in a love to hate/nostalgia kind of way but it is a TERRIBLE message.
Some department store…maybe Macy’s or Belk’s, I can’t remember…was running an ad earlier this month with a little girl singing this song. Eww.
I personally think Joseph Spence singing and playing Santa Claus is Comin to Town is delightful, but others I have played it for have thought it a bit creepy, if not just weird.
It’s…an acquired taste?
Is it meant to be weird or was he going for sincere?
Perhaps it’s an acquired taste. He’s influenced some well known musicians and his recordings have been released by several record labels.
Judging from some of the other recordings, his style is just his style, and not meant to be weird, IMO. This is pretty down and dirty folk music, and not in the “Mighty Wind” sense.
The minds that brought us the musical Urinetown wrote a ditty abotu Davey Dinckle, a child who likes to pee in the snow. He gets arrested, but the judge lets him off because it’s close to Christmas, as long as he agrees not to do it again.
Davey gave his word, but on Christmas eve a blizzard occured.
Which wrapped the twon in a blanket of white, that kept the town from Santa’s sight.
If Santa was to make to through, Davey knew what he must do
And then Davey Dinckle, no retreater, drank a liter of root beer.
Climbed to the roof and with a strong hand, peed in longhand"
WE’RE DOWN HERE
Santa saw the yellow glow and let out a big whole “HO HO HO”
And Santa’s sleigh set down, with presents for all the town.
Yes, Davey Dinckle he tinkled on the roof, and what was left was golden proof
That a chld could make the Chrstimas spirit fow (Christmas spirit flow).
Cause he tinkled on the roof and saved Christmas.
I vote “immeasurably hotter”.
I’ll be in my room now…
Dance of the Sugar Plum Fairy sounds kinda creepy.
Why all the debate about “Baby, it’s cold outside?” I thought we were talking about Christmas songs. 
That’s clearly a winter song, much like “Jingle Bells,” and “Walking in a Winter Wonderland.” (It’s just a personal pet peeve of mine that once the holidays are over, you never hear songs about winter and that have no holiday reference after Christmas, even though winter still has a couple of months left.)
My vote for creepy Christmas song goes to “Carol of the Bells,” which to me sounds like something from an “Omen,” type of movie with evil children.