The Best Christmas Song of All Time: Santa Sixteen, Pt. 1

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. To kick off the tournament, here’s our moderator, Deadshirt Music Editor Julian Ames

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#1. “Last Christmas” by Wham! (1985)


#16. “All I Want for Christmas is You” by Mariah Carey (1994)

Julian: Alright, let’s get this Christmas tournament started; the first matchup is already a doozy. On one hand we have the ’80s hit and #1 vote getter in our Deadshirt poll, “Last Christmas,” by Wham! It matches up against the strongest 16 seed in the history of any tournament, Mariah Carey’s “All I Want for Christmas is You.” Full disclosure, we actually forgot to include this one in the poll, but we realized our error thanks to many write-ins, so we got to include it anyway. Since we’re evil people, we’re gonna make Mike Duquette start off and choose between his two children. Take it away, Mike!

Mike: Jesus, from the word “go” I’m getting ‘Nam flashbacks to our James Bond bracket, the one where my beloved “The Living Daylights” bested a lot of (probably) better candidates for many rounds. On one hand, we’ve got “Last Christmas,” not only a bona fide Christmas classic but a song that has great personal significance to my career, as the person who came up with this mass-produced record. On the other hand, “All I Want for Christmas is You” is the perfect synthesis of A Christmas Gift for You from Philles Records and the sort of earth-shattering wall-to-wall soul-pop that Mariah Carey built a deservedly solid career upon. I saw Mariah on Friday during her second annual residency at The Beacon Theatre, and 21 years later she blew the fucking roof off the place. (I don’t think my girlfriend has ever “YAAAAAAAAAAAAS”-ed that hard in her life—and by God, she’s tried.) Ultimately, shockingly: That’s part of why my vote goes to “All I Want for Christmas is You.” “Last Christmas” is a typically brilliant pop confection by George Michael, who was only 21 when he constructed this earworm. The single upon which it was released, “Everything She Wants,” followed three straight U.K. chart-toppers (peaking “only” at No. 2 thanks to a busy Christmas No. 1 race that ultimately went to “Do They Know It’s Christmas”). But “Last Christmas” only underlined a killer career; Mariah’s tune kind of made one. She’d already had 11 Top 5 hits (eight of them No. 1’s) but was only starting to gain exposure outside of America. With “All I Want for Christmas is You,” she both defined a holiday and established her reign as international singing queen. I still love my project, but I can’t argue with that.

Max: This is a helluva opener to this bracket! This is like when badass Navy SEAL Steven Seagal dies in the opening of Executive Decision: NO ONE IS SAFE. I’ve come to really appreciate both of these songs over the last couple of years but as much as “Last Christmas” has grown on me, I gotta give this to “All I Want For Christmas Is You.” For one, it’s timeless: It came out in 1994, but it feels like it could’ve come out yesterday or like it’s a cover of an existing Motown Christmas hit. Maybe it’s corny, but “All I Want For Christmas Is You” *feels* vital; it’s a song that is everywhere in December, and I still never get tired of it.

Dylan: It’s unanimous! I have plenty of love for “Last Christmas,” but nothing can match the pure joy of Mariah Carey’s ultimate holiday love song. Eat your heart out, Phil Spector. (For a lot of reasons, actually.)

WINNER: “All I Want For Christmas Is You”

#8. “Christmas in Hollis” by Run DMC (1988)


#9 “Run Rudolph Run” by Chuck Berry (1958)

Julian: The second matchup finds the only hip-hop song in the tournament, “Christmas in Hollis” by Run DMC, pitted against Chuck Berry’s original rock and roll classic, that totally doesn’t sound like every other rock and roll classic, “Run Rudolph Run.” Hey, Max Robinson, who do you think wins?

Max: All due respect to Mr. Berry, a man whose place in rock history was insidiously tarnished by a time-traveling Marty McFly, but “Christmas in Hollis” takes this. “Run Rudolph Run” is a totally acceptable Berry jam but it really does kind of just sound like any other Chuck Berry song. “Christmas in Hollis” is near and dear to my heart because 1) It’s cute 2) It’s catchy 3) John McClane and Argyle listened to it in Die Hard, and 4) I gotta rep Queens. Dylan?

Dylan: Yeah, I’m with you boys. Chuck Berry’s “Great Twenty-Eight” is really more like the Great, Uh, Four with Different Lyrics. From the Clarence Carter sample to the appropriately corny early hip hop lyrics, “Christmas in Hollis” is a hoot. Chuck, man, I love ya, but this ain’t your day.

Mike: Even if I voted “Run Rudolph Run,” I’d be outvoted. But why would I do that? Give Chuck Berry the credit for rock and roll as a whole, but don’t tell me his entry in the Christmas canon breaks ground like “Christmas in Hollis.” The late, great Jam Master Jay’s killer scratching over Clarence Carter’s “Back Door Santa” is sublime, and this is probably the last fully focused Run-DMC track before the uneven Tougher Than Leather closed their book on the ‘80s. It’s “Christmas in Hollis” by a mile, rice and stuffing, macaroni and cheese and all.

WINNER: “Christmas in Hollis”

#4. “Christmas Wrapping” by The Waitresses (1981)


#13. “Jingle Bell Rock” by Bobby Helms (1957)

Julian: Next up, Ohioan new wave group The Waitresses takes Christmas into the ’80s with their delightfully catchy tune “Christmas Wrapping.” On the other side, the, at this point evergreen, “Jingle Bell Rock” by Bobby Helms is probably one of the most ubiquitous Christmas tunes in America at this point. Does the classic hold its own against the “new guard”? Whaddaya think, Dylan Roth?

Dylan: “Jingle Bell Rock” is a classic Christmas song—tight, repetitive, caroler-friendly. I also find it pretty grating, to be honest. There are a dozen songs that do what “Jingle Bell Rock” does better, like “Rockin’ Around the Christmas Tree,” for instance, which didn’t make the cut in our tournament. It’s an unambitious, inoffensive standard in a genre ripe with unambitous, inoffensive standards. I could take it or leave it. “Christmas Wrapping,” on the other hand, is unique among the December radioplay crowd, its rapid-fire lyrics telling a specific and yet universal story of yuletide exhaustion. While it admittedly overstays its welcome by about a minute and a half, it stands out from the pack and is charming as hell. My vote’s for The Waitresses.

Mike: A pall comes over me when I hear Bobby Helms’s version of “Jingle Bell Rock.” It does neither jingling nor rocking particularly well, especially in an age where Little Richard or Elvis Presley were there to scare the shit out of you with his devil’s music. It feels like a safe “rock” record your mom’s OK with you buying, a fact that I’d bet was referenced with a wink when Daryl Hall & John Oates cut their version in 1984. As for “Christmas Wrapping,” well…I would never tell you to know just one song by The Waitresses. They totally rule, and did some of the best underappreciated New Wave/power-pop of the early ‘80s. But if you had to know one song, it should be this. It’s a rare holiday tune that could still work with lyrics about anything else, which is very nice and kinda rare (imagine singing another song over “Sleigh Ride;” I bet you can’t). And the band, from songwriter Chris Butler’s killer guitar to Tracy Wormworth’s infectious bass and Patty Donahue’s laconic-as-all-hell vocals, is on point. “Christmas Wrapping” isn’t just a great Christmas song, it’s a damn great song, period.

Max: “Jingle Bell Rock” is fun, but it’s like the Christmas music equiv of mashed potatoes. I love it when I see it show up in a movie or a TV episode but it’s definitely not something I’ll actively seek out unless it’s the aforementioned Hall & Oates cover. “Christmas Wrapping” has been pretty firmly my favorite X-mas tune since I stumbled half-blind into my late 20s. I’m not even a huge fan of The Waitresses’ other work and this is like my go-to come December 1st. Like Dylan said, it taps into that near-universal feeling of running ragged between Thanksgiving and Christmas. Even if you don’t dig the space alien voices of The Waitresses, Mars Williams’s FUCKING INSANE sax solo and that bass line really distinguishes this from the usual yuletide fare.

WINNER: “Christmas Wrapping”

#5. “Santa Claus is Coming to Town” – Jackson 5 (1970)


#12. “Someday at Christmas” – Stevie Wonder (1967)

Julian: A soulful Christmas indeed, this matchup pits two acts that were at some point each on the revolutionary Motown label. The Jackson 5 version is the shining gem of the million versions of “Santa Claus is Comin’ to Town” that exist. Stevie Wonder’s “Someday at Christmas,” on the other hand, is the the O.G. recording. Which one of these two moves your soul more, Max?

Max: Can we all just admit this version of “Santa Claus is Coming to Town” is only on the list because MJ sings the shit out of it? He single-handedly makes this more than something you’d tolerate on a Spotify playlist. Really, these are both songs that live and die on who sings them. I’m giving this to “Someday at Christmas.” The socially relevant Christmas song is a mini-genre all its own, but even among similar tunes, there’s something uniquely touching about little Stevie Wonder belting out this appeal for reason, accountability and peace at a time when anti-Vietnam War sentiment was basically at its peak.

Mike: Christmas is worthless–worthless–without Motown Records. The Sound of Young America translated well to yuletide carols, and Motown holiday records remain some of my most treasured. The Jackson 5’s version, modeled on The Crystals’ game- (and chorus) changing version, is a worthy spectacle for young Michael Jackson, who’d given the J5 their second, third and fourth No. 1 hits that year (the first group to have their first four singles top the charts). But Max is spot on about the interpreter being key on this particular song. (Call me basic, but it’s Bruce or bust!) Stevie Wonder, only seventeen when he cut his eighth studio album, Someday At Christmas, was no stranger to singing for peace when the world was going to hell (a cover of Bob Dylan’s “Blowin’ in the Wind,” “Heaven Help Us All”) and would only get better at doing just that in the ’70s. His delivery here has more passion than even Michael could give at the time, and it’s a good reason why Stevie gets my vote.

Dylan: Well, this one’s decided already, so there’s no harm in me casting my vote with the Jackson 5 here. “Someday at Christmas” is one of the better political Christmas songs, and is performed with all of the passion and commitment we expect from Stevie Wonder, but Max put it perfectly when he said Michael sings the shit out of “Santa Claus is Coming to Town.” I’m also a big fan of the Springsteen version, and the Ronettes cut that inspired it. Anyway, well met, Stevie.

WINNER: “Someday at Christmas”

Four match-ups down, four to go! Check tomorrow afternoon for the second half of the Santa Sixteen!

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