A thing about me is that I love Christmas, but for the most part I hate Christmas music. I realize this may sound strange. Trust me, I really do go nuts for the holiday season — lights, decorations, baking, holiday movies, Santa hats, showering my 10-year-old with gifts, the whole nine. But the music isn’t a big part of that for me at all. Whether it’s because we as a society are forcefed a steadily increasing amount of it each year by advertisers and retailers, or because I’m naturally suspicious of music that is smarmy and nostalgic and indeed conservative by design, or because I live in Australia and songs about sleigh bells and snowmen in the summertime are just too absurd to bear, I have a troubled relationship with Christmas music overall.
Each year there’s a very narrow window of approximately two or three days, usually just Christmas Eve and the day itself, when I will actually put on Christmas music when I’m wrapping presents and such (keeping it down because my partner and my kid also hate Christmas music!). And on these very limited occasions, there’s a very limited list of Christmas albums that get repeat plays from me — five to be exact.
That said, though I only listen to them once or twice a year and then forget about them until the silly season (as we call it in Australia) rolls around again, I truly love these albums and they mean a lot to me.
Here they are, in chronological order of their release:

1. A Christmas Gift for You from Phil Spector (1963) — That violently abusive sexist creep and convicted murderer Phil Spector can rest in pieces, but this is an objectively amazing album. Separating art from artist is often tricky, but it works for me in this case; we can talk about what an awful person Spector was while appreciating his contributions to rock and roll as a producer during the girl-group era. But it’s even more to the point to give fuller credit to the artists, who were mainly Black women, and without whom Spector wouldn’t have made a name for himself: Darlene Love, the Ronettes, the Crystals, and Bob B. Sox and the Blue Jeans.
Of all the albums on this list, this is the one most likely to be hammered in retail stores, and its glories have been filtered down and diluted for later generations via greatly inferior covers. We 80s kids were permanently damaged by U2’s irritating cover of “Christmas (Baby Please Come Home)” — just thinking of Bono’s vocal on that makes my heart shrink like the Grinch’s.
But when you actually listen to A Christmas Gift for You at home it hits you right away how fabulous and unique and timeless it is. Buttressed by Spector’s famous Wall of Sound production, it’s a dense, bright, melody-saturated supernova of female-led Black rock ’n’ roll taking over the holidays and taking over pop culture. Love’s magnificent original version of “Baby Please Come Home” is obviously the standout, but as a lifelong fan of Ronnie Spector I also have a big soft spot for the Ronettes’ renditions of “Sleigh Ride” and “I Saw Mommy Kissing Santa Claus.” If you close your eyes you can picture how magical this album must have sounded in 1963, before the modern era of hyper-commercialization and Christmas’s illegal occupation of November (and October, and September).

2. Vince Guaraldi Trio – A Charlie Brown Christmas (1965) — This is the stone classic. It’s absolutely bulletproof, I never get tired of it, and it’s the album here that I’m most likely to listen to before December 24th or listen to multiple times.

You probably don’t need convincing, so I won’t go on at length. It’s not just a collection of Christmas music, not just the soundtrack of a beloved holiday special, it’s a proper album that holds up as a listening experience. Its blend of smooth Latin-tinged jazz and midcentury holiday nostalgia is so perfect — the very grownup, very urban melancholy of the jazz instrumentals adding so much richness and depth to the Peanuts milieu, and with that children’s choir, somehow both heartwarming and haunting, elevating the whole thing. It’s all so good that the sublime, generation-defining banger “Linus and Lucy” doesn’t dwarf the other tracks as you might expect at first; the enchantment and delights keep flowing over the rest of the album, which I often listen to twice in a row.

That “Linus and Lucy” and many of the other highlights are originals by Guaraldi is a big part of the album’s enduring appeal of course. His compositions are so classic that they basically are standards now. In fact I had to look it up to confirm that he wrote “Christmas Time Is Here”; it’s so integral to my conception of the holiday that I actually thought it was an older standard. Meanwhile, the tracks that are legit standards (“O Tannenbaum,” “Hark, the Herald Angels Sing” and the interpolated “Little Drummer Boy” among them) are exquisitely done and in Guaraldi’s hands don’t feel tired or played-out at all. This album is Christmas, or what Christmas should be if you ask me.

3. José Feliciano – Feliz Navidad (1970) — I was reading about the amazing life of the Mexican country singer Freddy Fender recently and it hit me what an influence certain Latin artists were on my 70s childhood. Feliciano was one of the biggest and this album, a favorite of my parents, was huge for us. Originally simply titled Jose Feliciano, it’s the quintessential Christmas long player for me, from an age when artists really put effort into their holiday releases, inhabiting that sweet spot between Latin, lush early 70s pop, easy listening, and classic rock, and instantly bringing back happy childhood memories. The title track is rightly celebrated as one of the best Christmas originals ever, but this album is chock-a-block with classic versions of standards like “Mary’s Little Boy Child” and “Silent Night.” Feliciano’s jazzy guitar instrumentals are gorgeous, and his version of “Little Drummer Boy” is in my book the best ever.

4. Willie Nelson – Pretty Paper (1979) — Two essential originals bookend this collection: the wonderful title track (written back in 1963 and originally recorded by Roy Orbison), and “Christmas Blues,” a ridiculously cool and funky instrumental that sounds like an outlaw-country version of “lo-fi hip-hop beats for relaxing and studying.” Other than that, this is a stock-standard collection of the most obvious Christmas songs that I suspect Nelson recorded in a couple of days to rush this album to market. But the thing about Nelson is, of all the artists out there, he’s the one who can make that really work. Listening to Willie sing “Winter Wonderland” or “Blue Christmas” in his inimitable jazzy, relaxed, stoned fashion is actually Christmas-music perfection and, true to the album’s title, makes for the best giftwrapping soundtrack.

5. Sufjan Stevens – Songs for Christmas (2006) — Stevens is the ideal Christmas musician because even his main body of work tends toward being profound, pretty, folksy, sentimental, overdone, maddeningly twee, and Christian in a weird secular way, and often features sleigh bells — just like Christmas music.
This 2006 release is a compilation of the five Christmas EPs the amazingly prolific Stevens recorded and released every year starting in 2001. The lush CD box set, with its terrific artwork and funny, weird, touching liner notes by Stevens, is for me a lingering, achy memory of Christmastime in New York in the 2000s and of a lost era of physical media.

This is definitely the best collection of contemporary holiday music for me, in part because you get the idea that Stevens, famously a progressive Christian, actually means this stuff. However my patience usually runs out after about the fourth disc, 90 minutes or so in, just like my patience runs out with Christmas music in general.
For this reason I’m not as familiar with Stevens’s second Christmas compilation, Silver and Gold, which includes Christmas EPs 6 through 10 (he kept doing them annually for many years, and might still be doing them for all I know). However if you love this collection I don’t think you can go wrong with any of the rest.

One of the best things about Songs for Christmas is that alongside the kitschy fun there’s an underlying melancholy to it — Stevens living up to his indie “sad boy” rep, perhaps, but it works for me. If Christmas music isn’t a bit melancholy there’s not much point to it as far as I’m concerned. Stevens explicitly connects this moodiness to his troubled childhood in the liner notes, as well as the lyrics of the actually heartbreaking “Did I Make You Cry on Christmas Day (Well You Deserved It),” from disc 4 (2005), which I think is about his late mom (also the subject of his 2015 masterpiece Carrie and Lowell).
The best EP here is the second one, from 2002; it has the strongest songs and the best balance between traditional and quirky new material like the excellent “Put the Lights on the Tree.” Stevens’s version of the 16th century English ballad “I Saw Three Ships” always kills me; it’s one of my favorite Christmas recordings of all time. If you actually make it to the end of the fifth EP you will be rewarded with the stunningly beautiful Steve Reichian/Michael Nymanish choral-instrumental “The Winter Solstice.”
Notes: My headline is slightly reductive; these five albums aren’t exactly the extent of the Christmas music I enjoy. There are a few other fondly remembered holiday classics that were big in my childhood, among them albums by Elvis Presley and Johnny Mathis. I always enjoy hearing songs from those ones when I’m Christmas shopping, but I haven’t listened to them at home since I was a kid. There are the great Christmas soul singles like Donny Hathaway’s magnificent “This Christmas” and “Santa Claus Go Straight to the Ghetto” by James Brown, but neither of those were included on full Christmas albums upon initial release so they don’t have a place to go on this list. I’m told that the Beach Boys’s Christmas LP is pretty great, and I don’t doubt it, but I just haven’t given myself a chance to listen to it yet. I suspect the same is true of Mariah Carey’s classic holiday album — and by the way, I think it’s unfair that “All I Want for Christmas Is You” has been reduced to being the butt of jokes and endless memes; I think it’s actually lovely. Yesterday I put on the 1999 Christmas LP by the great indie/dreampop band Low, and I thought it sounded pretty fantastic, but it was a bit too late to make this list.
The big point is that with only two or three days to indulge every year, inevitably my holiday listening is tightly circumscribed. I might have to expand my palette a little bit, and maybe I’ll even put together another Christmas top 5 for next year including a few of those I just named. Let me know what else you think I may have missed in the comments!
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Enjoyed your selection and comments. Two I’d add are the first Christmas album of jazz pianist Diana Krall and the first Christmas album by Johnny Mathis. Some consider it a bit smarmy but it has NEVER gone out of print in 60 + years. As a retired collector and event DJ , B B King’s Christmas Blues album of seasonal R&B standards is a masterpiece of slow dance and mid-tempo boogie blues for your
consideration.
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Thanks for reading, Doug! Really appreciate your feedback and suggestions. I grew up on the Johnny Mathis album, and I might have to consider publishing a follow-up list including that one, Elvis’s, Low’s, and Mariah Carey’s. 🙂
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