Back in 2015, I embarked on a journey to build the ultimate Christmas playlist. Now, 10 years later, it’s a 10-hour-long behemoth capable of soundtracking an entire night of yuletide debauchery without repeating (and hopefully without skipping). Every passing year brings new additions from friends’ recommendations, lightning-fast Shazam-ing, and happy accidents. You’d be surprised how many of your favorite artists have a dusty Christmas song buried in their back catalog.
So, in the spirit of giving, I’ve mined the hundreds of songs on my playlist and brought you 10 gems for your collection. Some are originals from classic artists that fell by the wayside. Some are obscure groups doing the Christmas classics justice. All are welcome editions to your own Christmas party soundtrack. So here they are, in no particular order:
1. Silent Night by The Singers Unlimited
This crystal-clean vocal jazz group can count King Krule and Flying Lotus among their fans. Their precise harmonies and vocal arrangements are unmatched on tracks like “The Shadow of Your Smile,” which they absolutely shred alongside the Oscar Peterson Trio. And their Christmas album (aptly titled Christmas) is no different. Honestly, the whole thing is gold, but the one that always makes me pause to admire its perfection is “Silent Night.” They way their voices blend on the line “Christ the savior is born” gives me goosebumps every time.
2. Player’s Ball – Christmas Mix by Outkast
If you’re familiar with the original version of “Player’s Ball,” then you already know the vibe. It’s 4 and a half minutes of Andre 3000 and Big Boi trading slick verses about their booze and mary-jane fueled Christmas exploits, over a jingle-bell-rockin’, head-knockin’ beat (there’s a clean version, too, for the faint of heart). Kurtis Blow and Run DMC might get more plays for their own holiday bars, but their style comes straight from the 80s. I’ve always preferred the mid-90s golden age hip-hop sound. Check this one out if you do too.
3. Christmas Time is Here by Khruangbin
Khruangbin transplants their signature funky sound from Thailand to your fireside with this criminally underplayed tune. Guitarist Mark Speer puts on a jazz masterclass that echoes and drifts like snowflakes in the air. It manages to strike the delicate balance of warmth and melancholy that Vince Guaraldi’s original compositions did so effortlessly (and so many other versions fail to do). Plus, the Youtube animation is a super cute homage to A Charlie Brown Christmas, where the song first appeared in 1965.
4. Every Day is Christmas by Charles Bradley and The Menahan Street Band
Picture this: post-Christmas party. You’re the host, and the guests have finally cleared out in the wee hours of Christmas morning. Nobody around but you, your equally dazzling hostess, and the aftermath of a night well spent. But before you settle your brain for a long winter’s nap, maybe some romance is in the picture . . . Is she thinkin’ what you’re thinkin’? And that’s the entire premise of Charles Bradley’s forgotten classic. With the impeccably soulful Menahan Street Band backing him – listen to the horn section splice “Jingle Bells” as a countermelody at 2:35 and tell me they aren’t brilliant – this tune would sound right at home on a 1972 Al Green Christmas album. Unfortunately, that album never got made. But Charles Bradley does a helluva job filling the void.
5. Socks by JD McPherson
This Oklahoma rock ‘n’ roll journeyman might not have struck gold with his non-holiday releases, but his all-original Christmas album (also titled Socks) might be one of the strongest sets of new Christmas songs to come out this decade. And the title track is a standout, perfectly encapsulating the dismay every child feels when they get hyped up for a paradigm-shifting gift only to tear open a 6-pack of Fruit of the Loom. The chorus of disgruntled voices layered every time McPherson utters the titular word is always hilarious to me, not to mention the deep subconscious voice that specifies exactly what kind of socks we’re dealing with in each verse (arrrrrrrgyyyyyyyle). The Christmas blues never sounded so playful.
6. I Heard the Bells on Christmas Day by Johnny Cash
Though the original lyrics date to a 1863 poem by Henry Wadsworth Longfellow, Johnny Cash makes this Civil War-era rumination sound like he penned it himself. If the boot fits, wear it. Longfellow’s poem delves into the bittersweet contrast of listening to joyous gospel hymns on the day his oldest son was shot fighting for the Union army. Grief and hope, intertwined. Delivering Longfellow’s lines slowly and deliberately, with his signature low-baritone drawl, Cash ages out of his country rebel persona and takes the form of a world-weary preacher. It suits him all too well
7. Five Pound Box of Money by Pearl Bailey
As the 1950s were coming to a close, Pearl Bailey put out this cheeky novelty tune that hasn’t lost an ounce of relatability. Atop a smooth big-band backdrop, Bailey raps casually to Santa himself about not wanting “the whole money tree.” No, far too unwieldy. She modestly asks for “just a little bit of the fruit.” A practical woman indeed.
8. Christmas in Prison by John Prine
A tender ballad that reads like a love letter from a prisoner to his beloved, sung with John Prine’s typical lack of embellishment. A simple man, spinning simple tales with heart and wit. Every topic he touches becomes more vivid with his every word. A penitentiary Christmas celebration is no exception. The Maywood bard never misses the mark.
9. Walkin in a Winter Wonderland by The Blenders
This one fits right in with the latest wave of 90s nostalgia. Striking a nice . . .blend . . .(see what I did there?) of Backstreet Boys and Straight No Chaser, this a capella quartet from Fargo, North Dakota boasts much more serious musical chops and creative foresight than their low profile suggests. The first time I heard this one, I thought it actually was one of the N’Syncs or Backstreets or 98 Degreeses of the world. Nope. Even better.
10. White Christmas by The Mistletones
The most obscure tune on this list by a long shot, I could find no solid information about this particular incarnation of the Mistletones except that they were pretty active in the mid 90s and they are NOT the similarly-named a capella group that’s been playing Dollywood for the last few years. Mysterious or not, the old Mistletones put together a killer rendition of this Christmas classic, and you can be the 200-somethingth person to hear it.
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