The 2023 Holiday Music That Doesn't Suck Playlist

Is it December already? This year went fast, probably because it was filled with change for me. After nearly 15 years in New York City (and after only 10 years of talking about it), we finally moved up to the Hudson Valley, where I’m now sitting in my office looking out the window behind my desk at trees and sky. I also started my second year of being in business on my own, and built a new brand for my coaching and training business. And I finally released my first album with my band, The Archivists. And then released a Halloween EP a month later.

I also took a trip to Iceland, saw a lot of my family and friends, watched a lot of horror movies, listened to a lot of music, went for a lot of bike rides, and drank a lot of really good beer. All in all, not a bad year.

Anyway, you’re not here for my holiday card. You’re here for…

Look at this horrifying AI-generated Santa! Why are there wires coming out of his head??

  1. Train - Shake Up Christmas
    Well, let’s get this out of the way upfront: despite this playlist being called “Holiday Music that Doesn’t Suck” [emphasis mine], this song kind of sucks. I’ve actually cut it from previous playlists at least four times. And yet. And yet here we are. I can’t get the little fucker out of my head. The harmonies are delightful, that dumb little riff is catchy, the rhymes catch my ear, and who cares if the lyrics are truly awful, I think I love this dumb song. I know nothing about Train other than that I’ve featured one other song of theirs on a past playlist. I guess I’m a fan (of their holiday album)? Ugh. Sorry, everyone.

  2. Sunturns - The Sun Turns
    I’ve featured this Norwegian band before, and for good reason. They’re a supergroup made up of members from a bunch of Scandinavian bands I’ve never heard of, and they’ve put out some truly lovely Christmas albums. This song chugs along like a train in the snow, and that jaunty little piano riff is the steam billowing out of the locomotive (at least that’s how I picture it). I featured their cover of Low’s Just Like Christmas back in 2021, you should check it out.

  3. Bing Crosby & The Andrews Sisters - Jingle Bells
    Bing Crosby was one of the first global superstars, appearing in over 70 movies and recording over 1,600 songs. He was also a philanderer, and an abusive father. And he came out in favor of marijuana legalization, on television, in 1977. And of course, for decades he was synonymous with Christmas. Guy contained multitudes, I guess. His holiday album with the Andrews Sisters is front-loaded and peaks early, but this song is a certified banger, all the way from 1961. It’s just begging for a trap remix, if you ask me.

  4. Phoebe Bridgers - Christmas Song (with Jackson Browne) (McCarthy Trenching cover)
    Phoebe Bridgers is a bit of a downer for my taste, and this one is no exception. I’m not familiar with the original by Nebraska band McCarthy Trenching, but this entry in Bridgers’s annual holiday release series is just beautiful and poignant, and what says “holiday season” more than breaking down and crying into your eggnog? Also I learned today that Jackson Browne (who’s on this track, but certainly not in a lead role) wrote the Nico song These Days when he was 16. Sixteen!

  5. Nicole Atkins - Every Single Christmas (JD McPherson cover)
    I featured JD McPherson’s original version of this one back in 2020; his version is more 50s sock hop while Nicole Atkins (who I featured in 2020 and 2022) goes full rockabilly with this spirited cover. I actually prefer it to the original at this point, it’s just got so much energy.

  6. Make Like Monkeys - A Little Bit To Us
    I don’t really know anything about this band other than that they have like 20 xmas albums. And a lot of their xmas songs are good! I like that this one is chill but they keep it moving, and I really dig the understated rhythm guitar part in the right channel throughout. This song feels vaguely nostalgic to me, just like the holidays in general.

  7. Swansea Sound - Happy Christmas To Me
    Named after a South Wales local radio station dating back to the 70s, this Welsh indie pop outfit turns in a decent take on the Ramones for this punky little number. You can almost see them practicing their sneers in the mirror. Apparently these guys are another supergroup, made up of members of other bands, none of which I have ever heard of.

  8. Grandaddy/Jason Lytle - It Was A Silent Night At Least Until Jeff Lynne Arrived
    This is not the space rock stalwarts’ first foray into name-checking famous musicians in their song titles (see: Alan Parsons in a Winter Wonderland), but this one seems to be a bit more heartfelt. Frontman Jason Lytle has gone on the record often about how much ELO’s Jeff Lynne and their music has meant to him, and it shows. He even sings a little bit of the tune to Turn to Stone at the end. 

  9. Meghan Trainor - Sleigh Ride
    Yes, I’ve featured Meghan Trainor on my playlists before. And yes, I might eventually feature every song on her dumb Christmas album. I can’t help myself. Like you’re so perfect? Her voice rocks and the arrangement is full without sounding overloaded. Long-time readers/listeners may know that Sleigh Ride is probably my favorite holiday season song, and her version is one of the best I’ve heard since TLC’s version, which you can hear here. And yes, I put two versions of Sleigh Ride on this year’s playlist. If you don’t like it, come at me, bro. I’ll see you in Hell. Happy holidays!

  10. Pink Martini - Ocho Kandelikas
    I usually find Pink Martini a little cutesy for my taste, but their holiday album has some gems, including this one. This is one of the best Chanukah songs, written back in 1983 in the rarely spoken Ladino language, which is a blend of Hebrew and Old Spanish. This one’s a real booty-shaker, by which I mean I always end up bopping my body along to it. It’s good and fiery for a cold winter’s night.

  11. Aimee Mann - Have Yourself a Merry Little Christmas
    I’ve featured Aimee Mann on my playlists too many times to link to. I’m a fan. This version is not as sad as Phoebe Bridgers’s version, but it is sad enough that I was once asked to remove it from a holiday playlist I’d put together for Washington Improv Theater’s holiday run of shows. I was told it was “bringing the audience down.” I can’t imagine why.

  12. Louis Armstrong (ft. The Commanders) - Cool Yule
    “From Coney Island to The Sunset Strip…” What a great opening image. This song is cool as hell and you don’t need me to convince you. Put down your nog and dance to this one.

  13. Jethro Tull - God Rest Ye Merry Gentlemen
    That’s right, folks, it’s the only band to canonically rock harder than Metallica. So… strap in for some jazzy flute, technically proficient piano work, and I do believe that’s a vibraphone in the background. This is another of my very favorite xmas tunes, and the flute fits right in with this little ditty that dates back to the early 1800s (the words go back to at least the mid-1600s). I love me some Christmas jazz, and Jethro Tull deliver the goods.

  14. Big Freedia - Jingle Bell Rock
    Many of you will want to skip this track. It’s painfully repetitive, loud, and more suited to a December peloton class playlist (which is where I’m pretty sure I first heard it) than a holiday music that doesn’t suck playlist, but I fucking love it and find it oddly soothing. The inside of my head feels like this song sometimes. Also Big Freedia is awesome. I mean, BeyoncĂ© sampled him, that’s gotta be worth something.

  15. Hanson - What Christmas Means To Me (Stevie Wonder cover but written by someone else, look it up)
    I’ve featured Hanson on a past playlist, and if no one stops me I’m liable to do it again. I don’t know who produced this album, but they mixed these songs to within an inch of their lives and I am here for it. Is it blasphemy to feature Hanson’s version of a song first made famous by Stevie Wonder? I don’t care, Hanson’s version rocks, and that’s that.

  16. Serge Fontaine - Promenade En Trai^neau
    I wasn’t able to find much (any) information on this French Hammond organist, but because the title is in French, I was able to sneak in a second version of Sleigh Ride on this playlist without anyone noticing. This version is so jaunty! It’s got a real bounce to it, a classic organ sound, and some tasty supporting guitar work. The bassline in the verses is also great once you latch onto it in the mix.

  17. Julian Casablancas - Christmas Treat
    Apparently the Strokes frontman wrote this little ditty as a joke, based on this SNL sketch where Fallon keeps fucking up the chords (he only has to hit 1 key at a time, come on, man!) and doesn’t know how to turn off his keyboard. The song took off unexpectedly, and finally Casablancas recorded this version, then went on SNL to upgrade the original with the help of The Roots. (And Fallon still managed to fuck up the chords!) For being intentionally dumb, this arrangement is awesome and Casablancas’s laid-back drone fits the made-for-TV tune perfectly.

  18. Lizzo - Never Felt Like Christmas
    Yes, I know Lizzo has been canceled. Well, allow me to cancel her again, because she does this amazing track a disservice by repeating the first verse instead of just writing another one. I wrote another verse in my head while listening to this the other day, and it wasn’t that hard! If I can do it, Lizzo can do it! Repetition aside, this romantic banger is fantastic, from those opening piano trills to the stacked horns to those amazing vocals. Good job, Lizzo. You’re still canceled, though.

  19. Connie Francis - I'm Gonna Be Warm This Winter
    Connie Francis didn’t just sell over 100 million albums worldwide. She wasn’t just the first woman to reach no. 1 on the Billboard Hot 100. I also learned this amazing nugget in her wikipedia entry: “In 1960, Francis was recognized as the most successful female artist in Germany, Japan, the United Kingdom, Italy, and Australia, and in every other country where records were purchased.” This track is from 1962 and it sounds like it, in every beautiful possible way. It’s also better than Kylie Minogue’s 2015 version, just FYI.

  20. The New Standards (ft. Allison LaBonne and Brian Tighe) - Snow
    The New Standards are a jazz trio from Minneapolis who have covered everyone from Rodgers and Hammerstein to The Clash and lots more in between. I don’t know much about this particular track, other than it doesn’t get called out in reviews of the album. The lyrics are simple, but it’s still not as vapid as Irving Berlin’s song of the same name from White Christmas.

  21. The Lathums - Krampus
    The Lathums are a British indie band. I don’t know anything about them. But this song is cool as hell. It doesn’t really seem to be about Krampus, but I dig the pre-chorus of “Santa ain’t coming this year.” And the chorus is fatalistic but optimistic: “Your Christmas will be canceled anyway/You might as well enjoy your time today”. I have no idea why he keeps yelling “Constitutions!” during the chorus. 

  22. Macy Gray and The California Jet Club - Merry Christmas Baby
    OK, Macy Gray is definitely phoning it in on this one, but it still works for me. That laid back arrangement from the California Jet Club does justice to the original without aping it. The piano is twinkly, her vocals are lethargic but it feels to me like an “end of a long night of holiday partying” performance as opposed to a lazy one. And the simple drum part works really well here.

  23. Carly Rae Jepsen - It's Not Christmas Till Somebody Cries
    I know very little about Carly Rae Jepsen other than that she’s Canadian, and my daughter loves the Gravity Falls version of her hit single Call Me Maybe. This song is kind of hilarious. “Grampa ate the gummies that we tried to hide/We had to play it off as a holiday high.” The harmonies are tight, the production is excessive, and the hook is catchy. Sounds like a Christmas cookie to me.

  24. Annika Norlin - Silent Night
    Last year’s guest Grinch turned me on to this odd, sad, beautiful, hopeful little number from the lead singer of the Swedish band Hello Saferide. It’s a retelling of the real story behind Silent Night along with some commentary, and it’s gorgeous. “9 out of 10 days are slightly disappointing/But on the 10th you see that light beckoning.” Here’s wishing you all a 10th day today.

  25. BONUS TRACK #1: De La Soul - Millie Pulled A Pistol On Santa
    I’ve almost included this track many times over the years, but it never felt quite right. It still doesn’t, to be honest, which is why it’s a bonus track. It’s not really a Christmas song, it’s much, much darker and more serious than that. But it’s still great. I was reminded of it recently when I heard The Roots’s version, which is dreary and dull compared to the original. 

  26. BONUS TRACK #2: Maximilian and The Reinhardt (ft. Jordan Hirsch) - Last Xmas
    Oh hey it’s me and Kevin Hill again! After our saxophone-heavy downer in 2021, we went metal in 2022 with this guitar-heavy downer about the coming climate apocalypse. Merry Xmas, everyone! PS If you want to support a great independent musician, check out Kevin’s work here.

Well gang, it's been another wild year, full of wonder and tragedy, magic and mayhem, strikes and gutters, ups and downs.

The Dude from the Big Lebowski saysing "oh you know, strikes and gutters, ups and downs"
The Dude knows what's up.
Here's wishing you and yours a very happy rest of the year. Thanks for listening, and as always, please tell me what you thought in the comments! Oh, and if you're into that sort of thing, you can download the whole thing here. Enjoy!

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