"Santa Baby" by Eartha Kitt
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Case for creepy: It's not just that the song is about an adult asking Santa for an increasingly extravagant list of gifts (convertible, yacht, etc.), it's also that they call Santa "baby" and make sexual overtures with lines like "come and trim my Christmas tree" and "hurry down my chimney tonight."
Case for classic: It's a cute novelty song that adds some much needed fun and flirt to the Christmas season. And, of course, Eartha Kitt is a legend!
"Baby, It's Cold Outside" written by Frank Loesser and popularized by the 1949 film Neptune's Daughter (seen below).
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Case for creepy: Let's start with the lyrics about a guy pressuring a woman to stay at his place. Hearing the woman sing "I ought to say no, no, no" and the man quickly respond, "Mind if I move in closer?" definitely makes you go "Yikes!" And then when she asks, "Say, what's in this drink?" and he complains that she might hurt his pride, well, it is way too reminiscent of horrible experiences women have had.
Case for classic: Didn't you see Zooey Deschanel and Will Ferrell sing it so charmingly in Elf? And the melody is a delightful ear worm. As for the lyrical criticism, some think that, when viewed through the lens of when it was written, the song is actually about a woman trying to exercise her sexual agency.
"Last Christmas" by Wham!
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Case for creepy: So the guy in this song gives someone his heart but the very next day they gave it away, which means their hookup or whatever lasted just one lousy day! And yet a year later he's still obsessing over this person! And then there's the part where he sings, "if you kissed me now I know you'd fool me again." Sheesh! Bro, give it up! Move on! It was one day!
Case for classic: George Michael sings the heck out of this total Christmas bop. And the song's conflicted, hurt narrator is what makes the lyrics so interesting and unique for a Christmas song!
"Santa Claus Is Comin' to Town" written by J. Fred Coots and Haven Gillespie
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Case for creepy: Santa comes off like a vengeful stalker in this song. The lyrics: "He sees you when you're sleeping / And he knows when you're awake / He knows if you've been bad or good / So be good for goodness sake" feel more like a threat than cute. And then there's "You better watch out! / You better not cry!" Who is this Santa? Robert De Niro?
Case for classic: This song has been making people feel good for almost 100 years, regardless of whether its sung by Fred Astaire or BTS! And when that chorus hits, I defy you not to feel a rush of excitement.
"The Christmas Shoes" by NewSong
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Case for creepy: This song is literally about a desperate boy trying to buy his near-death mother a Christmas gift of shoes because he wants "her to look beautiful in case she meets Jesus tonight." Oof. And the narrator is the man in line behind the boy who tosses in a few bucks so the kid has enough for the shoes, then says he knows God sent the little boy to remind him what Christmas is all about. So...God is putting this kid through all this suffering so the bearded guy in the baseball cap can remember the meaning of Christmas? That's...a lot to take in.
Case for classic: Come on! There is sadness in the world — even at Christmas — and the man's gesture helping the boy give his mother one last happy Christmas is beautiful! How can you not be moved? Is your heart made of stone? Good melody too!
"I Saw Mommy Kissing Santa Claus" by Jimmy Boyd
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Case for creepy: Even when you don't think too hard on this song, its concept — that a little boy doesn't recognize his dad dressed as Santa so he thinks his mom cheated on his dad with Santa — is creepy. But when you think on it a little longer and realize the parents didn't intend for the boy to see them, then you have to wonder: why was dad wearing the Santa suit? Is his dressing up some weird kink the mom and dad get off on every year?
Case for classic: Ugh! Why does everything have to be looked at from some weird, sexual angle? This is just a cute song where the listener understands what's going on more than the narrator — that's clever! Old school songcraft! And the melody works whether it's done country (like Boyd) or R&B/pop like in The Jackson 5's literally perfect cover.
"Grandma Got Run Over by a Reindeer" by Elmo and Patsy
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Case for creepy: Yeah, it's supposed to be funny, but a song about a grandma who gets drunk on egg nog, then goes out alone without her medication — only to get killed in a hit and run (by Santa, no less) — is a little dark. And then the song goes on, describing her funeral, their first Christmas dinner without her, how her husband doesn't seem to care...it makes me feel more unsettled than amused.
Case for classic: Yeah, it IS supposed to be funny, and it is! Details like the hoof prints on grandma's head and the table settings made to match grandma's wig are specific and clever, and having a song so out of left field play between the endless by-the-numbers Christmas songs every year is more than welcome!
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