24. “Good King Wenceslas” — Love Actually
Don’t worry, there are other entries from this movie (one of the best Christmas movies of all time, haters to the left), but I would be remiss if I didn’t include Prime Minister Hugh Grant, his honey-throated driver, Prime Minister Hugh Grant’s reaction to the aforementioned honey throat and these little girls dancing. Seriously, all haters can bah humbug their asses off the premises immediately.
23. “12 Days Of Christmas” — Scrubs
A quick little ditty from the musical-friendly sitcom Scrubs replaced “partridge in a pear tree” with “drunk who ran into a tree.” Not their cleverest effort but I think you can agree that Turk in clingy scrubs is a present we’d all like to unwrap.
22. “The Jolliest Fat Man” — Laverne & Shirley
Before he was cranking out songs for Christopher Guest flicks (Spinal Tap, Waiting For Guffman, the Academy Award nominated A Mighty Wind), Michael McKean was one half of TV’s favorite hapless musical duo “Lenny And The Squigtones.” Here’s their entry into the Christmas music catalogue. It’s a good one.
21. “The Instrument Song” — You’ve Got Mail
You know, unlike the Love Actually hate, the You’ve Got Mail hate is one I can understand. Yes, he lied to her! Yes, he kind of stalked her a little and emotionally manipulated her and basically Catfished her before we knew Catfishing was a thing outside the bayou. But the “he” in question is Tom Hanks and the “her” is Meg Ryan so, against all odds, the premise works. But you can’t have a rom-com love triangle without a dopey third leg. (The Ralph Bellamy/Bill Pullman Special.) In this instance, the dope is provided by the lovely Greg Kinnear. Never is his unsuitability as a suitor more evident than when he bombs this holiday sing-a-long with Ryan, Steve Zahn and the late, great Jean Stapleton.
20. “Make It Home” — My So-Called Life
There’s no way you can be neutral about this episode of the short-lived teen cult classic. Either you roll your eyes at it, or you fall for it hook, line and Rayanne Graff’s a binge drinker. As a child of the 90s, I’m in the former camp. I’m not religious, but bought Juliana Hatfield as an angel. If you, like me, were invested in this episode, then Juliana’s gentle (yes, angelic) song “Make It Home” will always make you think of Christmas. And Ricky’s fabulous eyeliner. And the way Jared Leto leans. And don’t you think Claire Danes should have stuck with the red hair?
19. “Santa’s Super Sleigh” — About A Boy
Another Hugh Grant movie! In this one, Grant isn’t the PM. He’s a cranky layabout Scrooge who’s living off the royalties of a Christmas pop monstrosity his father wrote. You can hear the whole thing in all it’s mawkish glory here. There’s isn’t a clip of it from the actual movie so you’ll have to make do with
Tiny Tim Nicholas Hoult crooning The Carpenters instead.
18. “I Saw The Light” — Orange Is The New Black
One of the best new shows of the year ended on a surprisingly high note. (Only surprising because it’s hard to put a satisfactory button on something as good as Season 1 of this show.) The finale centered around the prison holiday pageant (highlighted by that nice blonde lady maybe killing? certainly maiming? the wackadoo with the bad teeth). But the nice blonde lady story comes in second to the rest of the inmates including my favorite moment of the series: Annie Golden’s Norma taking the solo on “I Saw The Light” while wearing antlers made of tampons. That video’s not available, so enjoy this one of Poussey KILLING “Amazing Grace.”
17. “Snow” — White Christmas
Not the obvious choice from this movie, no, but we’ll get to that later. In the meantime enjoy the fun four-part harmony and earnest Danny Kaye-ness of it all.
16. “River” — Ally McBeal
This was my first introduction to RDJ’s singing voice. Here he nails the Joni Mitchell holiday classic. (“It’s coming on Christmas…”) The wheels sort of fell off the McBeal wagon in later seasons but I will always treasure this moment. Apologies for the poor quality.
15. “Jingle Bell Rock” — Mean Girls
You know for some reason I thought the girls did “Santa Baby.” That’s how slutty this performance is. “Jingle Bell Rock” became “Santa Baby” in my head. Wait. Slutty isn’t the preferred nomenclature is it? Smutty! It’s smutty! Or, er, sexually liberated! Anyway, the girls are cute, the song is great, the whole thing is bound to stuff your stocking unless you think too much about what happened to Lindsay Lohan. Don’t mess with the Lohan, focus on Seyfried and McAdams instead.
14. “O Holy Night” — The West Wing
I’m not a huge fan of the Whiffenpoofs myself, but their earnestly wholesome rendition of “O Holy Night” is the perfect background to this emotional episode of The West Wing. Note what Leo says here: “It’s four years later and there are things that are worse and things that are exactly the same. Where do you start?” That sense of defeat probably plagues every administration capable of self-reflection. How perfect, then, that there’s this tiny moment of grace.
13. “O Holy Night” — South Park
This is the diametric opposite of what The West Wing accomplishes and, yet, slightly more memorable. Maybe my second favorite Cartman musical performance.
12. “Hard Candy Christmas” — Best Little Whorehouse In Texas
This musical is such an enjoyable mess. I prefer the soundtrack version that just features Dolly, but recently rewatched this and couldn’t get over the styling on these holiday whores. So enjoy all the perms and spandex 1982 had to offer. Their ridiculousness can’t tarnish the pathos in Dolly’s voice.
11. “I Wish It Was Christmas Today” — Late Night With Jimmy Fallon
I could have picked any version of this song and I do feel a little guilty not picking one with Kattan and Morgan. But this performance elevated the song from fun SNL joke to legitimate Christmas classic. Horatio Sanz and Jimmy Fallon are great, but Julian Casablancas soars. Then it all comes back to laughter at the end when Fallon gently mocks Julian’s over-the-top crescendos. Perfection.
10. “Baby It’s Cold Outside” — Elf
Let’s leave out all the uncomfy aspects of this scene, shall we? The fact that Zooey Deschanel is showering in a department store (what? is that a thing?) by herself (creepy) and that Buddy is so socially inept and emotionally stunted (or, if you prefer, “innocent”) that he doesn’t see the problem intruding on her personal department store bathroom shower space. Then, of course, there’s the well-worn issue of the date rape subtext of the song. BUT. This was an early introduction to Zooey’s buttery rich voice before she went on to become the Queen Of Hipster Christmas. Don’t get me wrong, I like Buddy (and Will Ferrell’s sweet voice), but given his level of childlike cluelessness here, I’m not sure he should have gotten a love story.
9. “‘Tis The Season” — A Muppet Christmas Carol
I suppose there are lengthier, more polished songs from this Muppet classic I could have picked but nothing gets me quite as much as Kermit beep bopping up the street.
8. “Christmas Is All Around” — Love Actually
BILLY MACK! How could we possibly make this list without you? You folks might have done some juicy holiday chair dancing this season, but have you ever stool danced? Well, have you? Billy Mack elevates it to an art form. I feel it in both my fahngers and my toes.
7. “Adeste Fidelis” — Joyeaux Noel
I don’t have a lot of old school classic songs on this list. That is to say, for the most part, I tend to leave the Christ out of Christmas. It’s my own personal war on the holiday, if you prefer, Fox News. But it’s not that I don’t respect you or your faith, it’s that over the years the holiday has taken on such a secular meaning and I don’t like to exclude people. All that being said, this scene from the great French film about the Christmas truce of 1914 can’t help but blow your hair back. “O Come All Ye Faithful/Adeste Fidelis” has always been my favorite of the more religious carols but I never felt it as strongly as I do here with Rolando Villazón’s vocals and improbable bagpipes.
6. “Christmastime Is Here” — A Charlie Brown Christmas
One of my favorite podcasts recently did a whole segment on how this is one of the most hauntingly beautiful Christmas songs of all time. They’re not wrong. Haunting and moving and weirdly discordant for an animated show, this Vince Guaraldi classic endures.
5. “Put A Little Love In Your Heart” — Scrooged
Not a Christmas song? Are you kidding? Do you see the sprig of holly in Bill Murray’s cap? DO I HAVE TO STAPLE ANTLERS TO YOUR HEAD? I think we should make this one a sing-a-long. Starting with the women. The REAL women.
4. “Auld Lang Syne” — It’s A Wonderful Life
Take your cynicism and shove it.
3. “White Christmas” — Holiday Inn
I think most modern audiences are more familiar with this song from the movie White Christmas, but I always thought it fit better in Holiday Inn. The big lavish musical number at the end of White Christmas is fine, but this version is so much more intimate and the song itself comes back around, effectively acting as the emotional fulcrum of the film. Holiday Inn doesn’t get a lot of play anymore because of a deeply offensive and upsetting blackface number. Let that be a lesson to you, kids. Blackface ruins everything. Even Christmas.
2. “All I Want For Christmas” — Love Actually
What? You thought I’d only have two Love Actually songs on this list? HA! This is completely bananas showstopper. The get-out-of-your-seat feel-good climax of a feel-good movie. (Well not everyone feels good. Laura Linney and Emma Thompson get rather the short shrift.) So dress up in your fanciest holiday lobster costume, slap on some Spider-man faec paint and join us for the second best Christmas song of all time.
1. “Have Yourself A Merry Little Christmas” — Meet Me In St. Louis
Number one. With a bullet. Do you remember earlier how I said I like to keep the Christ out of Christmas? I do. I personally think the holidays should be about inclusivity. EVERYONE can enjoy Christmas how they want to enjoy it. Chinese food and a movie? Go for it. Midnight mass? Have at it. But “Have Yourself A Merry Little Christmas” has always epitomized the holiday for me. Here Judy Garland (at her most heartbreakingly beautiful, shot lovingly by her future husband, director Vincent Minnelli) sings to her little sister played by Margaret O’Brien just before they’re all supposed to move away from the family home. The song talks of “fates” and “faithful friends” and that’s something everyone can relate to. In 2001 the composer of this song, Hugh Martin, wanted to change the lyrics to reflect his faith and converted “Have Yourself A Merry Little Christmas” into “Have Yourself A Blessed Little Christmas” and the lyric about the fates became “if the Lord allows.” His changes didn’t really stick. The image of Judy burns too brightly in our collective conscience. So the song remains a melancholic but hopeful and secular ballad of love, family and friendship. Enjoy. Merry Christmas one and all.