Hi, this is Shane, and here are two moments from my past.
First, childhood. Any December; just pick one. And then pick a moment when I’m at home, trying to enjoy a videogame or a book or a TV show or something. Inevitably, the sounds you’ll hear come from one of two Christmas tapes (later CDs) that my mother plays on a constant loop from Thanksgiving until Christmas day. The first is Kenny Rogers’ Christmas, from 1981. The second is Miracles: The Holiday Album by Kenny G, from 1994 (apparently this one didn’t enter my life until age 11, thank God). As you can imagine, this was misery. Just try listening to Kentucky Homemade Christmas 300 times and see what happens to you. And look, it might be a good song; I can’t even tell at this point.
Moment two: Discovering Sufjan Stevens’ Christmas EPs in college. This was when I realized that Christmas music could be really, really good. It changed my whole outlook, and now, years later, my original hatred has been extinguished and I’m ready to make this list.
After discussing things with Paste editor and seasonal music PhD Bonnie Stiernberg, I realized there are really two categories of “Christmas music.” The first are Christmas-themed songs without any religious connotation (other than the word Christmas, I guess?). The second are the religious tunes like “O Holy Night” and “What Child is This?” and so on. So we’re making two lists. Bonnie is an expert at the former, so a lot of today’s entries come from her. Tomorrow, we’ll be tackling the absolute worst in the secular category, and next week we’ll get into the religious tunes.
Note: We’re focusing holistically on the song itself rather any particular version, though a really kicking rendition maybe kinda/sorta influenced us anyway.
Shane: I got the sense that Bonnie might kill me if I included this on the actual list, and even honorable mention was a stretch. But there’s something hilarious and wonderful about this song. It’s like someone said, hey, we need an Italian Christmas song, and then assigned the job to his half-crazed kid brother. I wish I could have been there in this fictional scenario when the kid brother came back with a song about a donkey. Anyway, it’s really fun and bizarre, so I hereby honor it!
Shane: More like BORING chestnuts roasting on a BORING fire. I’ve heard this song in far too many soulless department stores to even think about including it. Sorry, chestnut-heads.
Shane: I felt like we should start happy. Worth noting that there’s a character named Barney in this song who wants “hop-a-long boots,” which are apparently boots worn by Hopalong Cassidy, a fictional cowboy hero. So now you know that.
Bonnie: I still have no idea what this “new old-fashioned way” of dancing merrily is supposed to be, but it doesn’t matter. We can cut Brenda Lee some slack for being vague—amazingly, she was just 13 years old when she recorded this song.
Shane: Yeah, what does that mean? Modern hip-hop dance, but you wear a Roman soldier’s costume?
Shane: Charles Schulz’ main goal in life was to depress us, and in this song, Vince Guaraldi translated his vision perfectly. So, so sad. But we need something to listen to when we’re sad and lonely on the couch, after we’ve overturned the table and alienated our friends at the Christmas party. Plus, it’s pretty beautiful.
Bonnie: Added bonus: This one’s perfect for moping to year-round, as evidenced below.
Bonnie: Another huge, fantastic downer of a holiday song that just lays it all out there. I mean, it doesn’t get more matter-of-fact than “My baby’s gone, I have no friends.”
Shane: I think for this one, you really need to listen to the original Donny Hathaway version, which is awesome and has a lot of soul and a few jazzy interludes. There’s lots of maudlin potential in the wrong hands, though. Don’t even listen to the Chris Brown version.
Bonnie: Critics of this classic duet will argue its creepy message about consent is problematic, and that’s true to a certain extent (although it’s no “Blurred Lines”), but that denies the song’s female character any agency. I’ve always interpreted her part in this to be coy flirting, and some recent gender-swapped versions of this song like the Zooey-chases-M. Ward version by She & Him and the recent Lady Gaga-pursues-Joseph Gordon-Levitt take prove the male and female parts are interchangeable.
Shane: This is such a groove, and Cee Lo Green was the perfect singer to cover the iconic version sung by Stevie Wonder. Also, I like that they call tinsel “angel hair” in this song. I’m going to start using that, which means I’ll have to force tinsel into my conversations.
Bonnie: “Silver Bells” is admirable for attempting to chronicle that “feeling of Christmas” that finds its way into the air every year. The imagery it tosses our way, like “Strings of street lights / Even stop lights / Blink a bright red and green / As the shoppers rush home with their treasures,” is familiar, making it capable of getting even the Scroogiest of us in the holiday spirit.
Shane: Only Elvis could make sadness on Christmas day sound so sexy.
Bonnie: There’s a real elegance to “The Christmas Waltz,” some lovely imagery (“Frosted windowpanes, candles gleaming inside”) and warm-and-fuzzy sentiments (“It’s that time of year when the world falls in love”). Plus, it’s impossible to hear it now without thinking of one of my favorite Mad Men scenes of all time.
Shane: This is the opposite of Elvis’ “Blue Christmas” in that it sounds nice when you just read the title, and yet when you listen it’s seriously sad. Every single positive sentiment is either sung with extreme melancholy (“From now on our trouble will be miles away”) or has a qualification written into the very line (“Through the years we all will be together/If the fates allow”). It’s like watching your sad unemployed uncle stare into the fireplace after five Christmas mimosas and say something like, “yeah…things are really looking up for ole Russ.”
Bonnie: Don’t forget “until then, we’ll have to muddle through somehow,” a line that’s such a buzzkill, it’s removed from a lot of versions of this song and replaced with the cheerier “hang a shining star upon the highest bough.” I think that realism is what makes “Have Yourself a Merry Little Christmas” so remarkable, though. Not everyone’s Christmas is all gumdrops and merriment, and “Have Yourself a Merry Little Christmas” is an oddly comforting stiff upper lip of a song.
Shane: I’m officially intimidated by your Christmas song knowledge.
Bonnie: “Merry Christmas Baby” just feels…easy. Those sleigh bells and that groove take us to the best kind of Christmas morning: sipping egg nog in PJs and lazily opening presents with loved ones. And the lyrics confirm all this, with lines like “I feel mighty fine/I got music on my radio” and “I feel like I’m in paradise.”
Bonnie: I was doing some holiday shopping a few years ago when this song came on over the department store PA—as it surely did several hundred other times that December, and will every December until the end of time—and the entire store started singing along to it. The ENTIRE. STORE. Not a single person was unaware of the words, and everyone was smiling and bopping along to Mariah Carey’s modern classic and giving each other knowing “we’re all about to butcher this, but here goes nothing” grins when that insane high note kicks in. It was like something out of a cheesy made-for-TV movie, except it was real life, and it was great. And that’s the true meaning of Christmas, kids.
Shane: For everyone complaining that this isn’t the no. 1 song, I want you to know that Bonnie had it even lower. I fought for this, so please direct all your negative comments to her. Thank you. Anyway, the subtext of this song, which is that a soldier is writing a letter home from the war (that wasn’t Irving Berlin’s original meaning, but it was released in 1942 and resonated with the troops abroad) is still pretty gutting even after hearing it thousands of times. A classic. It also led to a hilarious quote from Bing Crosby, who gave credit to Berlin’s writing with some interesting self-deprecation: “A jackdaw with a cleft palate could have sung it successfully.”
Bonnie: I’m not saying this isn’t a great song. It is. I also wouldn’t be fulfilling my duties as an Otis Redding obsessive if I didn’t point everyone to his lovely version.
Bonnie: Okay, so yes, he turned out to be a crazy murderer, but man, no one put together a Yuletide tune quite like Phil Spector. Despite this song’s insistence that “they’re singing ‘Deck The Halls,’ but it’s not like Christmas at all,” nothing screams “Christmas” quite like Darlene Love belting it out over that famous Wall of Sound. Like “Have Yourself a Merry Little Christmas,” “Christmas (Baby Please Come Home)” is kind of a bummer, lyrically—not even the cheeriest-sounding bari sax solo can mask our narrator’s yearning for a love lost—but it manages to still sound festive. The strings, the bells, the choir of backup vocals…they all add up to a blast of seasonal sounds that’ll make your heart grow the proverbial three sizes.