The title is self-explanatory, so I will begin by stating the two rules, which, though I have just come up with them now, are rock solid:

  1. No song may hold more than one place on the list
  2. No musician or band may hold more than one place

You may feel the need to argue with my list. That’s fine, but this is the final word. And the final word does not include the Pentatonix.

10_Jessica_Simpson10.  “Baby It’s Cold Outside” — Jessica Simpson and Nick Lachey


This is the most abused Christmas song. Studios often slap people together whose voices are entirely incompatible (e.g. Norah Jones and Willie Nelson — WOOF) because they know it will widen their audience and rake in some serious dough. And it works because I unabashedly love this song.

There is only one other version I considered, and that was by James Taylor and Natalie Cole. They lost because James’ rich voice is too much for Natalie to handle — she only brings him down.

So considering how many marvelous talents have had a go at our only holiday duet (including the lovely—but predictably uninventive—new version by Michael Buble and Idina Menzel), why do Jessica Simpson and Nick Lachey, the Hollywood ex-couple no one cares about anymore, get top dog here? First of all, I’m with you. They both respectively suck. I will grant you that. I will also grant you that Lachey’s voice isn’t deep enough—not like Leon Redbone’s glorious baritone opposite Zooey Deschanel. And STILL this one wins. Why? Taking all the factors into account, I attribute this song’s greatness to the producers. The snare work is pronounced and peppy, there’s a bunch of saxes in the band that are just getting down, and Simpson and Lachey, if nothing else, have got some wild sexual tension.

Now you’re probably wondering why “wild sexual tension” is a positive attribute. Well, let me tell you: when a song has lyrics like “gosh, your lips look delicious,” the listener needs to be emotionally prepared to couple these two people together in their imaginations. So I’m sorry, but this absolutely rules out Zooey and Leon. It also rules out Dean Martin and his CHORUS OF GIRLS.

Note: Jessica’s breathy vocals make it very clear that she’s flirting with Nick and not being held captive—though their divorce may beg to differ.

9_Home_Alone9.  “Main Title from Home Alone” — John Williams

You may have negative opinions about Home Alone, but we can all agree that the score is a masterpiece of Christmas lovin’. It helps that staples like “White Christmas” by The Drifters accompany it, but even without the help, we’re left in John Williams’ more than capable hands.

A part of me wanted to put “Christmas at Hogwarts” in this place, but there’s that really uncomfortable bit with the ghosts mumbling “merry Christmas” over and over again, so that went out the window. BUT, that song still exemplifies a wonderful truth: John understands Christmas. He understands the warmth, the love, and the yearning that this holiday brings. Those realizations left me no choice: he had to make it onto this list.

But “understanding” is not enough to give you unarguable top ten status! There are plenty who understand Christmas—like Kenny G, of all people. He doesn’t make the list, but if I told you to listen to his album, I wouldn’t regret it. Anyways, what puts this track at number nine? It makes you long for Kevin to be back with his family more than the plot does.

8_Kenny_Loggins8.  “Celebrate Me Home” — Kenny Loggins

Now, this one is odd because it doesn’t even originate from a Christmas album. It was thrown in the middle of Kenny’s first solo debut of the same name. Anyone coming to it now in hopes of hearing some comforting Christmas sounds will be horrified when they listen to “Lady Luck” and hear Kenny growling over some guitar riffs that can only be described as very ‘70’s—which also adequately describes the cover art.

I can only assume this song made it onto people’s Christmas radars because it has the word “holiday” in it. Which led some genius at some point in time to pluck this song from Kenny’s album and pop it onto a Christmas playlist. Now we’re all stuck with the notion. It doesn’t even have a glockenspiel, for crying out loud! Regardless, it is now, unarguably, a Christmas song. And it is the eighth best one.

Given the holiday vaguery of “Celebrate Me Home,” many have been surprised, coming back home to their families, when this song comes on and suddenly THERE’S THE CHRISTMAS SPIRIT sitting right next to them, filling them with sweet memories of family adorned in ugly sweaters and holding snowman-shaped mugs full of hot chocolate. How? They wonder. There’s no mention of Christmas! To which I can only say: Santa Claus works in mysterious ways.

7_Whitney_Houston7.  “Joy to the World” — Whitney Houston

There is one person who could have overtaken Whitney here, and that’s Mariah Carey. Too bad for Mariah, though, she put a cheesy-as-all-hell electronic drum kit into the song and kept the vocal work oddly restrained. Sorry, Mariah, Whitney got it right: get a choir of the sassiest women you can find and then let them rip.

Let me be clear—this song was not that good before Whitney. No version of this song would have made the list without her. Not Percy Faith’s instrumental version, not Nat King Cole’s, and DEFINITELY not Three Dog Night’s piece of heresy. With Whitney’s finely tuned, powerhouse vocals riffing along with her choir and band, we finally heard what this song was meant to sound like. No one has done it better since.

6_Jars_Of_Clay6.  “Wonderful Christmastime” — Jars of Clay

I know, I know. This has got to be a frustrating experience for you. Aside from “Joy to the World,” I haven’t picked any classic carols. And when I did, I gave it to a remake by Whitney. Now, on top of that, you’re probably thinking: What! He picked a remake of a Paul McCartney song? He’s got no respect for the tradition!

You could not be more wrong! You could not be more flat-out wrong. I love the tradition. And one of the most wonderful facets of the tradition is the creativity that artists find year-to-year working with same material that’s been around for a century, sometimes more. It just so happens that McCartney wrote a great Christmas song, and Jars of Clay made it better. That is the way of Christmas music.

For the life of me, I couldn’t tell you why McCartney’s original is so good. It just is. It vibrates with holiday ambience. What Jars of Clay did better is fairly obvious: they took McCartney’s synthesized work and gave it real instrumentation. This created a fuller, more inviting sound. And when it comes to Christmas music, “more inviting” is a universal trump card. 

5_Winter_Song5.  “Winter Song” — Ingrid Michaelson and Sarah Bareilles

Ugh. Winter song?

That is probably this song’s only flaw. I don’t care what Ingrid and Sarah think, this is a Christmas song. It is reserved for that precious time after Thanksgiving and before December 26.

Evidence that it is a Christmas song: an entire segment is devoted to the lyrics “bum bum bum bum bum bum bum bum.”

Sarah is sad because she won’t be spending Christmas with her unnamed lover. Not December. Puh-leez.

Regardless, this song is a phenomenal piece of work. Every note is instilled with the patterns of Christmas music without being derivative. The simple piano work touches like falling snow. And Ingrid and Sarah have a very natural vocal chemistry that weaves the song together. Neither one is ever an over-powering presence. “Winter Song” is a modern Christmas classic, and rightfully so.

4_Hanson4.  “Merry Christmas Baby” — Hanson

YES. That’s right. I’m speaking of the Hanson—the very same beautiful, effeminate boys of “Mmmbop” fame. They kept making music? Yes. They kept making music. In fact, Hanson fans know it to be true that “Middle of Nowhere,” their first album, pales in comparison to their later work. Oh, you haven’t heard “Penny and Me?” What about “Been There Before?” YOU HAVEN’T HEARD “THINKING ‘BOUT SOMETHIN’?” I’m out of words.

In a rather odd move following their wild success, they penned a Christmas album. As far as I know, no one has been ever been foolish enough to do that. Mariah Carey waited four albums and she barely survived it—Merry Christmas still and will always cast a long shadow over the rest of her rather insubstantial work (yes, that includes her obligatory follow-up, Merry Christmas II You). While Hanson’s Snowed In is a quintessential Christmas album, without which no Christmas music library can claim to be complete, it may have been the fatal blow to their fame. Few people even knew Hanson attempted to keep going, let alone continued on to have a successful run as an indie band.

Yes, it’s true, the Hanson boys created a Christmas album to treasure. On the opening track, “Merry Christmas Baby,” you will hear exactly what makes it so good. It is, to quote from the journal I wrote when I was eight, “gamin,” which I take to mean “jamming.” The Hanson boys have voices with real soul, and effortlessly weave riffs together that jingle and jangle with Christmas spirit. It played like a classic seventeen years ago, and it plays like a classic now; hence number four status.

3_Relient_K3.  “Sleigh Ride” — Relient K

Oh, I’m sorry, you think Fun.’s version of “Sleigh Ride” is the greatest? That’s just too bad. It’s all sugar and no sentiment. Fun. does not understand Christmas. UNARGUABLE. Refer to rule number one and weep. Relient K made a far superior version back in 2007.

If any one band understands Christmas, it’s Relient K. Truly. I know they were pigeonholed as a Christian-youth-group-gathering music from days past, but they have grown and grown and grown. No band captures both the whimsy of Christmas music and its fill-your-heart-up-warmth, staying true to the tradition but adding enough quirks to continually surprise you like an official Red Rider carbine-action 200-shot range model BB rifle with a compass in the stock.

I can think of no comparable album to Let It Snow, Baby… Let it Reindeer that captures beauty, hilarity, and the raw, energetic passion that Christmas morning singly offers. “Sleigh Ride” exemplifies all of that. Listen to that jangly guitar tone, Matt Theissen’s silky vocals, and tell me that the Christmas spirit doesn’t burst into the room and dump a bucket of love over your head. If you need further proof, listen to their rendition of “Have Yourself a Merry Little Christmas.” Then listen to “Good King Wenceslas.”

WARNING: A lot of older material resides in that behemoth of an album, most of which was carried over from their previous Christmas offering Deck the Halls and Bruise Your Fist. It’s the newer material I’m speaking of here, not the older—very important clarification to make before you stumble upon the sins of their youth.

2_Mindy_Smith2.  “Santa will Find You” — Mindy Smith

Picking one Mindy Smith song from her album My Holiday is a chore. The record is a cold, snowy kiss on a rosy cheek. It makes your heart sad it passed so quickly.

Every song on it is perfectly done. If not for rule number two she would take up half this list. Her version of “The Christmas Song” is the only one I can claim to love more than Nat King Cole’s. Likewise, her “I’ll Be Home For Christmas” is as special as Bing Crosby’s ever was. In fact, every classic she covers is on par with the originals. She’s a classic, and barely anyone knows about her.

But her album isn’t special because of her covers; it’s special because of her originals. They’re SO good. They should be added to the Christmas canon. This is a claim I cannot make for Relient K and Hanson. Relient K has a few good originals, but they are not “canon” material outside of the Relient K-verse. And Hanson’s originals are undeniably the weakest part of Snowed In.

One of Mindy’s standout originals is “Santa Will Find You,” a beautiful song for lonely hearts. It seeks out the lonely and loves them. But really, you should just listen to the whole album so you can find treasures like “I Know The Reason” and “It Really is (a Wonderful Life).” Marvelous, marvelous stuff.

1_Cambridge1.  “Candlelight Carol” — Cambridge Singers

Do you feel misled? You probably should. Here I’ve been leading you to believe that I only listen to relatively modern Christmas music, and suddenly I drop this on you— a traditional carol, and a rather obscure one at that, sung by a choir. It is what it is. Sometimes the best Christmas music is older than the hills and just as immovable. If you aren’t familiar with “Candlelight Carol,” it really is my pleasure to share it with you.

This is the perfect Christmas song—and by that, I mean this: it is the best Christmas song ever written and performed by anyone, hence the irrefutable number one status. I hold this song dearest to my heart.

This song is a night of thick flurries. It is reading a book by a crackling fire and a Christmas tree. It is starlight on a field of snow. It is a wink from Santa Claus. It is touched with bittersweet and glowing with heart. It is filled with Holy Spirit. This song, dare I say, resonates around the grand walls of the Hogwarts dining hall during Harry’s first Christmas there. At least, it should.

As with the past three contenders, the entire album is superb, and no Christmas music library is complete without it.

Gather with your family on Christmas Eve, tell them you love them, bundle up and look at the Christmas tree, and listen to this song. If nothing else, love them. That is why we listen to Christmas music, I think. It reminds us how much we love.


Honorable Mentions (no order)

Driving Home for Christmas” — Chris Rea
Believe” — Josh Groban
Marshmallow World” — Bing Crosby
Christmas, Why Can’t I Find You” — James Horner and Taylor Momsen
Jesus, Oh What a Wonderful Child” — Mariah Carey
Oh, Holy Night” — Josh Garrels and Mason Jar Music
Last Christmas” — Jimmy Eat World


  1. Elaine

    ….your Christmas joy makes me uncomfortable. But at least there is no Pentatonix on this list. I suppose you have a soul. Still, no Vince Guiraldi trio??

    • Will

      Great suggestion! I DID consider them. But the two rules stopped them from making it on. For instance, if one musician or group has a better version of another musician or group’s best song — e.g. the Cambridge Singers version of “O Tannenbaum” is better than VInce Guiraldi’s — but say, The Cambridge Singers are already on the list for another song, I still cannot put Vince Guiraldi on the list, or even that song. A lot of great songs are missing on this list because of the Cambridge Singers and Mindy. Also, most of the songs, even though excellently conceived and performed, end up becoming background music.
      There is my crazy long response.

      • Elaine

        Appreciated. My favorite thing about this post was the rigorous methodology. Seriously, I’m turning in a *research paper* this semester with less justification for my methods.

  2. Avatar

    Quick comments:

    — can’t have a list with the date rape song on it. Seriously bugs me. (Sorry to be crass. But that song drives me crazy.)

    — What?! No Sufjan?!?!

    — sarah maclachlan and bare naked ladies ‘we three kings’ is an insta-classic, too. Love it.

    Fun list. Thanks!!!!!

    — Steph Seefeldt

    • Will

      I’ll grant you the date rape anger. I included it on the list because I’ve always interpreted the female part as flirtatious, which I do think is intended within the song. Real life situations differ, though, and this song should not be used as a template for reality.

  3. Avatar

    Ugh. I may revise my post this month to be the definitive Top 10 Worst Christmas Songs Ever — partly to cheer up Elaine, but also partly because there is a little overlap between your list and mine.

    • Avatar

      Don’t revise! Let’s go toe to toe and duke this thing out.


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