10 of the Most Awkward Christmas Songs of All Time

Olivia Newton-John, John Travolta, This ChristmasUMe

Ah, the holidays. A time for family togetherness, the warm embrace of friends, and crippling awkwardness.

With nearly every artist who has access to a microphone and some jingle bells deciding to put out a Christmas album, the sheer glut of holiday music makes it inevitable that we’ll have some clunkers. Or, if they’re not complete clunkers, that they’ll leave us scratching our heads over a lyric or two. Here are ten of our most favorite awkward holiday songs.

*N Sync — “Under My Tree”

“Bring along the mistletoe
Keep the music nice and low
I’ll show you how good it could be.
I wish that Santa could be here to see
It’s beautiful under my tree”

No word yet on whether or not Santa likes to watch.

Michael Bublé — “Santa Baby”

Bublé must have run out of Christmas standards to cover, because his version of the slinky Eartha Kitt classic is just confusing. This song is about flirting with Santa. Take that away and it’s just a grown man begging for presents. “Santa buddy?” No.

Dolly Parton — “Hard Candy Christmas”

Awkward mostly because it’s just so depressing, The hookers’ tale of woe from The Best Little Whorehouse in Texas is actually a pretty fantastic song. But we wouldn’t recommend it for your party playlist.

Olivia Newton John and John Travolta — “I Think You Might Like It”

Danny and Sandy reunited to bring us a cheese-covered holiday duet album, and this one’s the kicker. Olivia and John sing about “doing a little dance,” “making love all night” and then watching It’s a Wonderful Life and crying. And then someone’s drunk mother makes an appearance? It’s thoroughly unexplainable.

Lady Gaga featuring Space Cowboy — “Christmas Tree”

What is it with pop stars singing about getting it on under Christmas trees? Do people do this? Aren’t there pine needles jabbing into you? Where do you put the presents?

Liza Minnelli and Alan Cumming — “Baby, It’s Cold Outside”

Clearly, one of the more inspired versions of this predatory Christmas song. Halfway through, the parts flip and Liza is pursuing Alan. Still creepy, but at least it’s equal opportunity creepy.

Weather Girls — “Dear Santa (Bring Me a Man This Christmas)”

We have no problem with the sentiment — get yours, girls — but really, it’s just a slightly holiday-ed up version of “It’s Raining Men.”

Girls Aloud — “Not Tonight, Santa”

I have a headache. Why don’t you go play your XBox?

Clarence Carter — “Back Door Santa”


Justin Bieber featuring Mariah Carey — “All I Want for Christmas Is You (Superfestive!)”

Oh, but this time it’s superfestive? This is the real life version of Billy Mack’s “Christmas Is All Around.” A cash grab in musical form.