The Best Christmas Song of All Time: Santa Sixteen, Pt. 2

It’s the holiday season, the only time of year that comes with its very own genre of music. This Christmas, Deadshirt staffers Mike DuquetteMax Robinson, and Dylan Roth decided to comb through the massive, diverse canon of Christmas songs to determine which is the hands-down greatest of all time. Using a pool of songs selected and voted on by our readers on social media, we’ve whittled it down to sixteen songs, arranged on a March Madness-style bracket. Now to our moderator, Deadshirt Music Editor Julian Ames

X-Mas 16 Bracket Color 2

(click to enlarge)

Round One – The Santa Sixteen (Part 2)

#2. “Another Lonely Christmas” – Prince and The Revolution (1984)

(No video anywhere. Tidal or bust, I guess)

#15. “A Patrick Swayze Christmas” – Crow T. Robot (1996)

Julian: This matchup is pretty fascinating because, I don’t really know either of these songs, so I can’t really do a good intro. Hell, I’ll wing it. Prince rules, so I’m sure that when he puts his insanely talented mind to making a Christmas song, it’s probably incredible. MST3K is also a great program, one I admittedly don’t watch enough of, so I’m sure the song is at least funny. What do you think, Mike?

Mike: “Another Lonely Christmas,” the flipside of Prince and The Revolution’s “I Would Die 4 U,” is a seriously strange, funky stream-of-consciousness track that’s only tertiarily a holiday song, as the narrator mourns his holiday without a deceased lover, who passed away on the day Jesus was born. As Purple Rain-era ideas go, it’s jockeying for position among a cache of seriously great B-sides (“17 Days,” “Erotic City”), light on guitar theatrics but heavy on emotion and some impressive jazz drumming.

As for “Patrick Swayze Christmas,” the subject of a spirited campaign…maybe it’s the poor taste in my mouth over this MST3K Kickstarter thing, or maybe it’s some implacable Grinchiness. But I like both MST3K and Road House, and I barely cracked a smile at this one. It’s kind of like hearing a hilarious high school joke repeated to you as an adult. Prince may be wacky as hell walling off his catalogue on Tidal, but he wins this round.

Dylan: Like Mike said, I gotta admit neither of these songs really hit me in the pocket where I keep my Christmas spirit. But if it’s a choice between a decent Purple Rain B-side and a decent Joel-era MST3K host segment, well, I’m more of a Nelson guy, be it Michael J. or Prince Rogers. Point Prince.

Max: Two songs that are hilarious for different reasons. If you know me, you know how important MST3K and Prince are to me. “A Patrick Swayze Christmas” is a hilarious…I struggle to call it a song because it’s really just a good skit… about a Roadhouse creation myth, but it can’t touch Prince’s sadly crooning about “drinking banana daiquiris until [he’s] blind” or checking out his dead girlfriend’s younger sister while she’s ice-skating. I could write one of those 33 ⅓ books on the insane weirdness of “Another Lonely Christmas”. Sorry, “Patrick Swayze”…it looks like Prince is stayin’…and YOU’RE goin’.

WINNER: “Another Lonely Christmas”


#7. “Father Christmas” – The Kinks (1978)

vs. #10. “White Christmas” – Bing Crosby (1954)

Julian: Talk about two completely different Christmas tunes! The Kinks’ kick-in-the-ass, punch-in-the-face proto-punk anthem “Father Christmas” is a far cry from the Bing Crosby orchestral-tinged standard that is “White Christmas.” So what do you think, Dylan, are we gonna have a white Christmas, or an angsty Christmas?

Dylan: Bloody hell, this is brutal. On the one hand, “Father Christmas” is the ultimate punk rock Christmas song. It’s catchy, it’s bratty, it’s got a monster hook and a pinch of social commentary. But shit, man, up against an ironclad classic like “White Christmas”? That’s a tall order. Bing Crosby’s famous number from a movie musical that actually holds up really well is practically the polar opposite of the jaded ironic “Father Christmas,” and has inspired hundreds, if not thousands, of reinterpretations. I’m partial to The Drifters’ version myself, in fact it’d probably get my vote if it was on the card for this bout. These songs are both terrific, and my pick comes down to nothing but personal taste. I love The Kinks, I love “Father Christmas,” and while I don’t expect it to win the round, it does get my vote.

Max: I think the pre-1960s classic holiday standards are going to be obliterated by this bracket, as much as I love ‘em. “White Christmas” is the kind of thing you wanna hear at your mom’s house on Christmas Eve, and it’ll be around long after we’re all gone. But I’m voting “Father Christmas” because, hey, find me a better song about British hooligans beating the shit out of some well-meaning guy dressed up like Old St. Nick. “Father Christmas” is kind of all over the place, but you gotta admire its scrappy meanness when most other Christmas songs are all about being way too happy, way too sad or way too horny during the holidays.

Mike: Not being familiar with “Father Christmas” (but one of the first to say The Kinks’ Arista Records tenure is better than you might have recalled), I was all prepared to give my vote to “White Christmas,” one of the most perfectly yearning Christmas songs as well as the biggest-selling single of all time. Ultimately, though, the combination of Ray Davies’ Spector-esque arrangement and snotty social commentary won me over. Kinks for Khristmas it is!

WINNER: “Father Christmas”


#3. “Christmas (Baby Please Come Home)” – Darlene Love (1963)

vs. #14. “The Christmas Song” – Nat King Cole (1946/1961)

Julian: Of course, all these songs are Christmas songs, but perhaps more than any of the other matchups, these two songs are really CHRISTMAS songs. You’ve got the Phil Spector production and Darlene Love’s pipes singing “Christmas (Baby Please Come Home)” up against the gentle, yet definitive croon of Nat King Cole on “The Christmas Song.” Max, start us off, which one are you going with here?

Max: This is like choosing between my own children. If I had children that weren’t Lego versions of Batman, I mean. “The Christmas Song” evokes very specific, powerful memories for me: Christmas Eve at my Grandma’s house in Annapolis, Leonardo DiCaprio’s Frank Abagnale in Catch Me If You Can fleeing federal custody to his mother’s house and discovering she has moved on without him in his absence. I love this song; it’s the spirit of Christmas to me top to bottom.

So it sorta sucks that I have to give this to “Christmas (Baby Please Come Home),” which is the emotional equiv of a gatling gun. Darlene Love puts so much heartache, want and anger into one song. The best Christmas songs are at least a little sad, I think, and this is the sad Christmas song other sad Christmas songs aspire to be. There isn’t a fully realized story being laid down here or anything, just the vague beats of one that matter: Baby, come home, it’s Christmas. I think this one is going to be the top dog when we get to the end of this bracket, it’s just so killer. Anyone who listens to this song and feels nothing is a monster.

Mike: This choice is almost as terrifying as the Wham!/Mariah debate. Two titanic songs of the season, definitively sung by each, drowning in heartache and beautiful instrumental tracks (Ralph Carmichael’s orchestration on “The Christmas Song” is gorgeous–that piano/guitar break gets me every time–and the motherfucking Wrecking Crew play “Christmas (Baby Please Come Home)” like it’ll be their last.) Ultimately, Darlene Love edges just past Nat “King” Cole, God bless him, thanks to her perfect utilization of one of pop’s best tropes: sounding exhilarated while feeling inconsolable. Bring on the sax solo!

Dylan: This is hands-down the toughest matchup for me in the first round, because I love both of these songs to death. Thankfully, you boys have taken the pressure off by already voting in “Christmas (Baby Please Come Home),” so I don’t have to worry that I’ll be disqualifying one of my favorites by casting my vote for Nat King Cole. I love the classic Phillies Records Wall of Sound, I adore Darlene Love, and “Christmas” ranks as one of my favorite pop songs overall, any time of year, but “The Christmas Song” brings tears to my eyes every single time I hear it. Cole’s delivery of Mel Torme’s gorgeous melody is so subtle and yet somehow so emotional that it makes my breathing stop. It’s not knocking the wind out of me, per se—this isn’t a soul tune, there was no such thing yet—it’s more like I’m holding my precious breath and savoring the moment, the beautiful season of family, charity, and song.

WINNER: “Christmas (Baby Please Come Home”


#6. “Fairytale of New York” – The Pogues (1987)

vs. #11. “Skating” – The Vince Guaraldi Trio (1967)

Julian: In this last matchup of the first round, we get two sort of left-field picks. “Fairytale of New York” is possibly the most popular Christmas song in the UK, and the most beautiful thing ever remotely attached to The Pogues, but it’s not nearly as well known in the US. “Skating” is the instrumental jazz tune that appears throughout A Charlie Brown Christmas; composed by Vince Guaraldi and performed by his jazz trio, this song is a curious, but cool, addition to this bracket. Mike, what do you think of these two?

Mike: My extremely hot take on The Pogues is my favorite song of theirs lacks Shane MacGowan’s droning vocals (1993’s “Tuesday Morning”). “Fairytale of New York” is fine, and God strike me down if I speak ill of the late Kirsty MacColl, but it’s no “Skating.” It’s no A Charlie Brown Christmas, which is an album so good I’m infuriated it’s only seasonal. “Skating” remains an inspired choice for this thoughtful bracket, and I’m happy to see it and vote for it.

Dylan: What to say about “Fairytale of New York”? Well, at the very least it’s my favorite Christmas song to include the word “f*****.” No foolin’, I really love this song. There are Christmas love songs and Christmas heartbreak songs, and “Fairytale” manages to be both. It’s romantic and cynical, miserable and festive, and I can’t think of too many songs like it in the holiday canon. As for “Skating,” it’s certainly a pretty piece of music, but here at the end of the qualifying round I can’t help but think of all the better songs that didn’t make it into the Sweet Sixteen. Sinatra’s “Have Yourself a Merry Little Christmas,” Brenda Lee’s “Rockin’ Around the Christmas Tree,” a host of other classic and contemporary Christmas jams that could just have easily been part of this tournament. So, I gotta pour one out for the losers—in this case, The Poor Ole Pogues.

Max: I’m probably the biggest dork who smokes weed “jazz guy” of the Deadshirt set so I was really glad to see at least one of the Guaraldi Charlie Brown tracks make the bracket. The jazz compositions for “A Charlie Brown Christmas” are going to outlive us all, our techno-ancestors will be listening to this on Mars or that cylinder colony thing that McConaughy’s kid builds in Interstellar. “Skating” is a song you can play for anyone, anywhere and you can say “This is Christmas.” I’ve got a lot of love for “Fairytale”: It’s an uncompromising song, unfortunate slur and all, and if this was “best song to sing drunk with your friends at a Christmas party” it’d be #1. As it stands, however, I’m calling this a rare victory for Charlie Brown.

WINNER: “Skating”

Check back next week as our tournament continues to the Elite Eggnog Eight!

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