The 2021 Holiday Music That Doesn't Suck Playlist - Naughty & Nice Edition!

Welcome back, fellow lovers of great Christmas music, happening Hanukkah tunes, and holiday music that doesn't suck. How was your year? I have mixed feelings about mine: while the world seems to be sliding ever faster into destruction and autocracy, it was actually a pretty good year for me personally. So today, I'm choosing to focus on the positive, because a little positivity can be really helpful when times get tough.

This year, I:

• Started a coaching business. After struggling to figure out what the hell to do next in my career, I finally realized (with the help of a coach) that I'd been coaching people for years, and even using that word to describe myself, without ever considering hanging out a shingle. Well, my shingle's out, I love the work, and it's amazing to watch my clients grow. I'm still working on building up my hours for certification, so please reach out for a complimentary session if you'd like to be less miserable and enjoy your life a bit more.
  
• Biked my first century ride 🚲💯. After having my brand new beautiful bike stolen in 2020, I got the best bike I could afford with the insurance money (during a global bike shortage) and decided not to let that stop me from my goal of riding 100 miles in a single day. It was amazing and I actually want to do another one next year.
  
• Started a new role at my day job. After years of trying to carve out the right role for myself at the digital agency where I work, I finally created a job that's a perfect blend of my strengths, skills, and work I love - and one that creates value for my company and our clients. And that feels pretty damn good.
  
• Started the process of buying a house in the Hudson Valley, a place where I've spent the vast majority of my vacation and travel time over the last decade. It won't be ready for a while, but I'm ready to make some memories there.
  
• Watched 31 horror movies in October. I know, it might not sound like an "accomplishment," but it's something I aim for every October, and it was a really fun milestone to hit (again).
  

Why am I sharing all this with you? As a reminder to take some time and focus on the good things from your year - even when things are hard, focusing on what you're grateful for can have a real positive impact on your mental health. Speaking of mental health, I've had more than one person tell me how much these playlists matter to them and how helpful they are in stressful times, and that means the world to me. So without any further ado (though I do love me some ado), let's get to this year's playlist...I mean playlists.

I always have a hard time editing these things down to a "reasonable" size, but this year I realized I'd made full playlists for 2021 and 2022 and was starting to compile some tracks for 2023... and I realized I didn't want to wait that long to put this out into the world. So I decided to do a double playlist this year, organized by the theme of Naughty & Nice. What does that mean? Well, it means that for each song I wanted to include, I listened to it and then made a gut decision on which category better fit. I'll explain some of my thinking behind the categories in the long descriptions no one reads. I also decided to let myself break some of my "rules" this time around - for instance, I'm using 3 versions of the same song across 2 playlists in 1 year! And I'm not sorry about it! Maybe it'll inspire you to break some of the rules you're carrying around in your head, too.

And with that last bit of ado, let's get to the tunes:

Part 1: Naughty

1. My Only Wish (This Year) - Britney Spears | 2000. A simpler time, when all we needed was Santa to bring us our one true love (and maybe get us out of that pesky conservatorship, though that wish might take a few years). Britney recorded this peppy little number for a compilation album, and I think it's a great way to kick off this year's naughty list. WHY NAUGHTY? She's basically asking Santa to bring her someone to bone, so, naughty. Also features an unearned key change, which, also naughty.
   
   
2. The Grinch - Undecided Youth | This young band (I think they started when the guitarist was in high school) from Arizona won some Alice Cooper-sponsored battle of the bands a few years back and that's literally all I know about them. WHY NAUGHTY? It's about the Grinch, duh. Also they're playing heavy metal guitars, and you know that's naughty.
   
   
3. White Christmas (Guitar Stooge Version) | That little "ho ho ho" from Iggy at the top of this sets the stage nicely for the next 4ish minutes of that terrifyingly deep baritone balancing a precariously twangy guitar and somehow also being White Christmas at the same time. Iggy Pop, described in a tweet I saw recently as the only man who looks ridiculous wearing a shirt, brings a decidedly un-punk attitude to this cover, which I guess is maybe the most punk thing you can do. WHY NAUGHTY? It's Iggy Pop doing White Christmas, you figure it out.
   
   
4. Little Drummer Boy - The Dandy Warhols | I love how the Dandy Warhols pull off the trick of being fastidiously sloppy on this track, really epitomizing the word "slack." WHY NAUGHTY? They skip a chord change each time through for reasons unknown, the backing vocals come in late, the whole thing is just so damn lackadaisical and yet it never falls apart like it keeps threatening to. That's naughty.
   
   
5. Stop the Cavalry - Jona Lewi | English musician Jona Lewie had a hit in the UK in December 1980 with this catchy little anti-war number. The whole thing's extremely British, including the uniquely British thing of being a Christmas hit that's barely a Christmas song. WHY NAUGHTY? It's a Christmas song that's not about Christmas (though it does get mentioned a couple times). It's also unfairly catchy for being about war.
   
   
6. Snow is Falling in Manhattan - Purple Mountains | This sleepy number from David Berman's last album (before his tragic suicide in 2019) is thick and lovely, the aural equivalent of a big, wet snowflake falling on a cold city night. WHY NAUGHTY? City snow is inherently naughty because it immediately turns to dirty slush. Plus Berman was just kind of a naughty guy.
   
   
7. Up On the Housetop - Chris Mann | I've featured Chris Mann on here before, and every time I feel like I have to apologize for his over-produced brand of insanely catchy pop production. Well, this year is different: I'm done apologizing. At least 50% of Chris Mann's Christmas EP is fantastic, and I'm not sorry about it. WHY NAUGHTY? The guy was on The Voice, that's just fucking cheesy. Plus he called his PBS concert special Chris Mann in Concert: A Mann for All Seasons so, you know, naughty.
   
   
8. Sleigh Ride - TLC | This version of Sleigh Ride is nearly unrecognizable for most of the playing time, and that's awesome. TLC really puts their own spin on one of my very favorite holiday tracks, and they manage to do justice to a classic while making it unmistakably their own. WHY NAUGHTY? That "giddy-up" part is clearly very naughty, as well as being amazing. The whole irreverent take on the source material is definitely naughty. Awesomely naughty.
   
   
9. Just Like Christmas - Sunturns | You people are always demanding more Norwegian super-groups on these playlists, right? Well, happy Chanukah (it's night 6 as I write this), motherfuckers. This band has been described (by themselves) as "five of Oslo's finest singers, musicians, and songwriters," so you know they're good. This song is actually kind of hauntingly beautiful once you let it under your skin a little, as its a pretty faithful cover of Low's original. WHY NAUGHTY? They're spending a Christmas song singing about "driving home from Stockholm." That's clearly naughty.
   
   
10. Carol Of The Bells - The Luvmenauts | This Toronto-based musical collective brings a peppermint-cool touch to this old repurposed Ukrainian folk song. The trippy guitar, slightly off-kilter drums, spooky organ, and glockenspiel work together to funkify a nearly 100-year old Christmas tune, which is a neat trick. WHY NAUGHTY? The glockenspiel, mostly.
    
    
11. Oh Hanukkah - Jack Black | The 2019 "Hanukkah+" compilation was very exciting for me - there's just not a lot of great Chanukah music out there - but I was ultimately disappointed by nearly every track on there. With the exception of this one. Jack Black plays it for laughs in the choruses, but the verses are pure candle-lit beauty with those backing vocals that are sweeter than gelt. WHY NAUGHTY? Black tries to have his latke and eat it too - either take the song seriously or don't. Also this uses my less-preferred spelling of the Festival of Lights. "Chanukah" forever.
    
    
12. Blue X-mas (To Whom It May Concern) - Drunken Boat | Drunken Boat came out of the same 80s New York scene that spawned bands like Bongwater and King Missile, but I'd never heard of these guys until last year. Despite the notable handicap of having a poet for a frontman (who sounds like a slightly off-key Perry Farrell), they bring a great slacker energy to this sort-of-but-not-really cover of the Bob Dorough/Miles Davis cool jazz experimental number from 1962. WHY NAUGHTY? They covered the spirit but not the music or words of the original. 
    
    
13. tis the damn season - Taylor Swift | Supposedly this Swiftean holiday bummer is a counterpart to her track Dorothea from the same album, about a famous woman who returns to her small hometown and rekindles her relationship with her former lover, even though she knows the relationship's doomed. I'm sure it's not autobiographical at all. It's also beautiful with a fantastic hook and poetic lyrics. Good job, Taylor. WHY NAUGHTY: It's a Christmas song about a breakup, and being sad at Christmas (while fairly standard) is definitely naughty. Also the word "damn" is right in the title, Santa's not gonna like that.
    
    
14. Christmas Tears - Eli Cook | Speaking of being sad at Christmas, this track from Eli cook (who I just learned is a fairly young white man, and not a fairly old Black man, as I assumed after hearing this song), is all about having the Christmas blues. It eschews the trope of having broken up at Christmas and instead is about missing an old lover every year around this time: "I hear sleigh bells ring/I haven't heard from you in years." Damn. WHY NAUGHTY? That blistering guitar solo. Ain't nothing nice about it.
    
    
15. Sleigh Ride - Zigo & Joan Rochette | This version of Sleigh Ride is chiller than a snowflake, makes tasteful use of a robot-y arpeggiator, and is cool AF. What's not to like? Try as I might, I was unable to find any information about either of these artists. WHY NAUGHTY? Because it's the second occurrence of Sleigh Ride in the same playlist (and there's another one coming later!). I am being very naughty by doing this.
    
    
16. Seasonal Shift - Calexico | Tucson's own Calexico (yes, this band named after a city in California is from Arizona) released a pretty great Christmas album this year of the same name. The second line of this song is "It's been disastrous/But somehow we'll get through" which is a pretty great mantra for any of the last several years, and lines like "Mom and dad/Now with gin & tonic in hand/Are more relaxed" make this song a potent mix of realistic and optimistic, which is a great attitude for the holiday season in my book. WHY NAUGHTY? It's about real stuff instead of just candy canes and elves and snow and whatnot.
    
    
17. Little Drummer Boy - Justin Bieber ft. Busta Rhymes | Didn't I already put a version of Little Drummer Boy on this playlist? Yes, yes I did. There are no rules any more. No gods, no masters. Bieber muses aloud in this track about how he's surprised that his music wasn't featured in the bible. The kid's got chutzpah, and I respect that. It also features Busta Rhymes wishing me a happy Chanukah, which is something that doesn't happen often enough. WHY NAUGHTY? Justin Bieber. Busta Rhymes. 'nuff said.
    
    
18. I Won't Be Home For Christmas - Poppy | LA-based former performance artist Poppy turns in a heartbreaking performance on this sparse little number, having made her decision not to return to a former love. "Where are you now/I can't tell how long it's been" - damn that's sad. WHY NAUGHTY? She mentions "the 110," and the way LA people put "the" in front of road numbers is just naughty.
    
    
19. All I Want for Christmas is You - Kelly Clarkson | First, let's clear this up - no, this isn't a cover of *that* All I Want for Christmas is You, it's the other one, the one by New Orleans country pop outfit Vince Vance & the Valiants. The same band that sang "Bomb Iran" to the tune of the Regents' Barbara Ann long before John McCain would embarrass himself doing the same thing. Kelly Clarkson can sing, and really goddamn well. I loved her last Christmas album, I'm very excited to hear her new one, and I love her cover of this criminally overlooked Christmas tune. Horns, people. Horns! Even synth horns are good horns! WHY NAUGHTY? It's my favorite kind of Christmas song - one about fucking. It's more oblique than, say, Back Door Santa, but we all know what she's singing about here.
    
    
20. Santa Claus - Spectrum | Peter Kember AKA Sonic Boom, had many musical identities after the breakup of foundational psychedelic rock band Spacemen 3. One of the more accessible ones is the band Spectrum, who turns in a Christmas track that sounds like everyone's been hitting the eggnog a little too hard (especially the keyboardist, who leaves in plenty of sour notes from what really sounds like a first take). I recently learned that this song is a cover of a track by 1960s garage rockers The Sonics. WHY NAUGHTY? He's asking Santa for "a cute little honey/drugs and money" and you know Santa is probably going to have a problem with all of that.
    
    
21. BONUS TRACK: Blue Christmas - Jordan Hirsch & Das Binky | Last year I fulfilled a long-held dream of recording a Christmas tune with my friend John, who's one of my oldest and dearest friends and musical collaborators. I went with a version of Blue Christmas because I love that song and because I could hear our future version clearly in my head. The final version isn't quite what I pictured when we started, but that's the fun of collaborations. I love my arpeggiator solo in this one, and also all of John's performances and production choices. WHY NAUGHTY? I'm putting my own track on my playlist! That's very naughty. Also I want to re-do all the vocals because they're full of naughty imperfections.

OK, everyone. You made it through Naughty. Take a big sip of your Christmas ale, adjust your Santa hat, and get ready for the horror that is... Nice.

Part 2: Nice

1. Christmas Time Is Here - Barry Manilow | I know, I know, Barry Manilow has a reputation for sucking. But I'm here to tell you, his 2007 Christmas album is actually really fucking good. I know, I wouldn't believe me either. His version of Vince Guaraldi's happy holiday wrist-opener is almost 2 versions in one: a beautiful instrumental take on the original is the hot mug of cocoa, then Manilow's vocals pour in like a shot of peppermint schnapps. WHY NICE? It's innocent, it's beautiful, it's Barry freaking Manilow.
   
   
2. Happy Xmas (War Is Over) - Dean & Britta | Luna's king & queen released a live-streamed holiday show last year, and it was a silver lining in a very, very bad year. While Dean's voice isn't holding up as well over time as Britta's, there's something undeniably sweet about their chilled out version of Lennon's cynically hopeful holiday tune. WHY NICE? They take the source material seriously, and the whole thing is as pretty as fresh snow.
   
   
3. We Three Kings - Dolly Parton | Dolly's version of this 1850s carol starts out with a cold wind, but Dolly's voice soon warms things up. But this is no cozy night by the fire - she brings passion and energy to this one, keeping the whole thing moving. And the dulcimer cuts through everything like an icicle. WHY NICE? It's Dolly Parton, she's a goddamn national treasure.
   
   
4. Ding Dong, Ding Dong - George Harrison | Based on the old doorbell chime and with lyrics inspired from engravings Harrison found at his nineteenth-century home, this New Year's singalong has a little bit of Spector-inspired production, a lot of Harrison sounding like himself, and enough leftover charm to keep you warm all winter. WHY NICE? It's just so damn silly and fun and sweet, nothing naughty about it.
   
   
5. Fairytale of New York - Gavin James | Sad (I'm assuming) Irishman (that one's certain) Gavin James strips this Pogues holiday hit down to little more than his arresting voice and the barest instrumentation. The guitar is reminiscent of Simon & Garfunkel at times, and the whole thing is just so stark and lovely. WHY NICE? OK, the content is decidedly naughty, but James's take on the material is so beautiful, it swings it over to nice for me. And I'm the only one who gets to vote, so there.
   
   
6. Merry X-Mas Everybody - Steps | British dance-pop outfit Steps turns up the "upbeat" dial on this already upbeat tune by Slade. The mixture of autotune, synths, and Christmas bells makes something wonderful, like when you mix raw eggs, cream, sugar, and booze to make the greatest drink on earth. WHY NICE? Once again, the content here is definitely naughty (the lyrics ask "do the fairies keep him sober for a day?" about Santa), but they just sound like they're having so much fun!
   
   
7. Last Christmas - Taylor Swift | Didn't I already have a Taylor Swift song on the last playlist? Yes, yes I did. But this is classic country Taylor, from a little over a decade before the sad, bitter Taylor from that other playlist. Stalwart listeners of my playlists will know that I love this song and usually include a version of it, and Taylor's version has been on my "maybe" list for too long. She makes it her own, and brings her vocal A-game like she usually does. WHY NICE? She makes this super-sad Christmas song about heartbreak sound... fun.
   
   
8. The Christmas Party - The Goo Goo Dolls featuring the Union Square Five | This jazzy holiday medley is so good, and sounds nothing like the Goo Goo Dolls, that I had a hard time believing this was the same band who rocketed to fame in the 90s with Iris. I don't know who the Union Square Five are, but I'm assuming they're doing some of the jazzy jazz heavy lifting here. WHY NICE? It's like 10 holiday songs in 1. What a bargain!
   
   
9. Early Christmas Morning - Cyndi Lauper | Cyndi Lauper's 2 Christmas albums are actually pretty good, and this original is a real standout. If I didn't know who this was, I might assume it was an Irish folk band. But Lauper's vocal delivery gives her away, and I love that this is the same woman I developed a major crush on the first time I saw the video for Girls Just Want to Have Fun when I was around 7. WHY NICE? It's about children! On Christmas morning! Super nice.
   
   
10. Rudolph The Red-Nosed Reindeer - The Temptations | The Motown stalwarts bring enough soul to Rudolph to power his red nose all through the night. You just don't get groups like this nowadays, with 5 incredibly strong singers all in one band. Nearly every Motown Christmas song I've ever heard is good, so expect more of them over the years. WHY NICE? Despite the taunting of the other reindeer, Rudolph takes the (literal) high road, rather than leaving Santa and his clique of asshole animals in the darkness like they so richly deserve.
    
    
11. Jingle Bells - The Infamous Stringdusters | Modern bluegrassers The Infamous Stringdusters bring way more to this humble little tune than it deserves, and we're all the richer for it. Slide guitar, banjo, dobro, fiddle, double bass - this track has it all. Every time I think I'm tired of Jingle Bells, this version reminds me that there's more here to love. WHY NICE? It's a bluegrass Jingle Bells, how much nicer can you get?
    
    
12. Merry Christmas, Baby - Otis Redding | I've featured several versions of this song on playlists past, but somehow never got around to giving Otis Redding's standard-setting version its moment in the sun. Well that ends tonight. WHY NICE? It's literally about how his "baby" "sure did treat [him] nice." Treating people nicely is nice.
    
    
13. Keeping the Dream Alive - Freiheit | While this not-about-Christmas-but-popular-at-Christmastime-in-the-UK song by German band Freiheit should be on the naughty list for stealing its chord progression from another Cyndi Lauper song (the not-about-Christmas-but-coincidentally-named-the-same-as-a-Christmas-song All Through the Night, if you're curious), I can't stay mad at this song. WHY NICE? It's just so damn cheery and optimistic and it makes me want to be a better person or possibly I'm drunk on a very strong Christmas Imperial stout from KCBC that my awesome wife got me for Chanukah.
    
    
14. Christmas All Over Again - Tom Petty | Man, I miss Tom Petty. I've been a big fan of his for more than a couple decades now, but for some reason I never put his early 90s Christmas tune on a playlist until now. The words are dumb, but it's got bells, a driving guitar line, and Tom Petty's loving sneer delivering lines like "Christmas is a rocking time." What's not to like? WHY NICE? It's Tom Petty, that's why.
    
    
15. Linus And Lucy - Nick Lowe and Los Straitjackets | This instrumental is probably more Los Straitjackets and less Nick Lowe than the rest of their combined holiday album, but that doesn't make it any less awesome. I love the little ska-esque guitar holding it down on the up-beats in the verses. WHY NICE? It's a lively cover of a classic tune that has nothing to do with Christmas. Do my reasons still have to make sense when I'm doing the write-up for my 35th song of the night? No. No they don't.
    
    
16. Sleigh Ride - Ella Fitzgerald | Another version of Sleigh Ride? Am I crazy? Yeah, crazy for... Sleigh Ride, I guess. Ella's swinging 1960 take on this light orchestra standard from 1948 manages to become a vocal showcase for her without taking any attention away from the source material or the arrangement. WHY NICE? She sings "giddy-yap" instead of "giddy-up," and I find that nice.
    
    
17. Deck the Halls - The Twang-O-Matics | Yes, I put all the instrumentals on the Nice list. No, I don't remember why. Anyway, you might not guess it, but this instrumental combo who claims to play "the most frenzied, honkin', and reverbin' instrumentals the world has ever heard" actually hail from Norway, and their version of Deck the Halls is indeed frenzied (slightly), honkin' (definitely), and reverbin' (totally). WHY NICE? I guess instrumentals are nice because the words don't get in the way and naughty everything up.
    
    
18. It's Beginning To Look A Lot Like Christmas - Meghan Trainor | Is there such a thing as so over-produced that it comes back around to being just the right amount of produced? I don't know, but this song sounds like the soundtrack to an auto-tuned winter wonderland Christmas fever dream, and I for one am here for it. WHY NICE? Trainor manages to make a song from 1951 sound believable in 2020, and that's a pretty nice trick. Also her harmonies are dope.
    
    
19. Have Yourself a Merry Little Christmas - Leslie Odom, Jr. | Leslie Odom Jr.'s Christmas album is a wonderful showcase for his voice - and what a voice it is. At turns powerful and sensitive, it's clearly a well-loved instrument and he knows how to play it. His version of this 1943 downer takes a jazzy turn about halfway through, going off in an unexpected direction for a while, then merges the old and new together in a way that every cover should strive to do. WHY NICE? That voice. It's the egg in my nog.

Well friends, we've nearly made it through another year. Whenever you're reading this (and yes, I'm assuming at least one of you read all the way to the end), here's hoping that you and yours are happy, healthy, and surrounded by music that doesn't suck. I hope you enjoy this year's double playlist, and thanks for making me a part of your holiday tradition.