The 5 Most Unsettling Holiday Songs Of All Time

It’s the holiday season, and in the immortal words of Andy Williams, “Whoop-de-doo and dickery dock, and don’t forget to hang up your sock.” Yes, it’s the time of year when the limited daylight starts to get to us and we go a little nuts. As a result, we do weird things like stick a tree in the middle of our living room, wear retina-damaging sweaters, and drink egg-nog (which is pretty gross, let’s be real). But we also sing songs that we’d probably find pretty creepy at any other time of the year. So with that in mind, let’s walk together in a winter wonderland of wayyyy unsettling holiday songs!

5. “I Saw Mommy Kissing Santa Claus” (originally sung by Jimmy Boyd, 1952)

Lyrical Evidence:

She didn’t see me creep
Down the stairs to have a peek
She thought I was tucked
Up in my bedroom fast asleep…

Oh, what a laugh it would have been,
If Daddy had only seen

Verdict: There is no way you can convince us that this track isn’t about adultery. How is the boy not traumatized by the sight of his mother mackin’ it with some old beardy dude in his own living room? On Christmas, no less! Sure kid, it’s “Santa”...keep on telling yourself that.

Bonus Points: The original version by Jimmy Boyd was banned by the Catholic Church for associating kissing with Christmas.

4. “Santa Baby” (originally sung by Eartha Kitt, 1953)

Lyrical Evidence:

Santa cutie, and fill my stocking with a duplex,
And checks.
Sign your ’X’ on the line
Santa baby, so hurry down the chimney tonight.

Santa honey, there’s one thing I really do need,
The deed
To a platinum mine…

Verdict:  Honestly, we really don’t want to hear about Santa coming down some demanding woman’s chimney, slipping a sable under her tree, or any of the other thinly veiled euphemisms for him getting his bells jingled. And where the hell is Mrs. Claus!? The track paints a portrait of St. Nick as a sugar daddy to some gold-digging ho-ho-ho, and we aren’t gonna stand for it! *this face*

3. The Nutcracker (by Tchaikovsky, 1892)

Lyrical Evidence:

Da da dum dum dum dum
da da da da da da da da da da da
dum de dum de dum

Verdict: It’s not so much the words (or lack thereof) that make the ballet so unsettling, but the plot. It’s about a knife-wielding toy that comes to life in the middle of the night. Didn’t they make a horror movie about that? Factor in the battle with a giant rodent king, and you’ve got a recipe for holiday fear.

2. “Baby, It’s Cold Outside” (originally sung by Ricardo Montalban and Esther Williams, 1948)

Lyrical Evidence:

The entire song.

Verdict:  Here’s a song about a holiday date from hell. Sure, it started off nice, but now the evening is winding down and the girl wants to head home. This isn’t what the guy wants to hear, and he tries every trick in the book to keep her there. These include guilt (“What’s the sense in hurting my pride…how could you do this to me?”), drugging (“Say, what’s in this drink?”) and finally implying that he might die if she leaves. This song could be an episode of CSI. Someone needs to tell this dude that no means no.

1. “If You Sit On My Lap Today” (originally sung Mickey Rooney, 1970)

Lyrical Evidence:

If you sit on my lap today
A kiss a toy is the price you’ll pay
When you tell what you wish for —
In a whisper
Be prepared to pay.

If you sit on my lap today
A kiss a toy is the price you’ll pay
When you sit on my left knee
Don’t be stingy
Be prepared to pay!

Verdict: Somebody call Chris Hansen! This song always struck us terribly wrong, from the moment we first saw it on the stop-motion holiday special, Santa Claus Is Coming To Town as kids. Any way you slice it, there’s no getting around the fact that a large man is inviting children to sit on his lap and making vaguely threatening demands to kiss him. That’s more than enough to vault this tune to the top of our unsettling Christmas songs list.

Bonus Points: The song is now cut from most airings of the television special, allegedly to make room for more commercials. This is one case where the commercialization of Christmas is probably a good thing.

[Photo: MGM]

VH1 Music Editor + Seltzer Enthusiast