What may be contrary to popular belief is that I am not an apathetic curmudgeon when it comes to the holidays. Christmas is my favorite holiday—the cheeriness, the romance, the snow; I’m privy to the “magic” that comes around this time of year. Much of that is owed to the type of music played, which can range from wonderful to “Please, God, make it stop.” In the spirit of the holidays, I wanted to detail my ten favorite Christmas songs ever, because why not?
For context, I listened to many songs in preparation for this list. I didn’t want to just go, “Uhhh, let’s listen to a ‘Best Christmas Songs 2021’ playlist on YouTube and choose from that.” No, I went out of my way to listen to all types of Christmas music. I must have listened to over a hundred songs, performed by a variety of different musicians and performers. Things both “stereotypically Christmas” and completely against such tradition. My hope is that this list covers a decent variety of different tones.
Will also provide a disclaimer that I did not put any repeat artists or songs on this list. If I did, there’d be, like, four choices by the same artist or three of the same songs. Again, I strove for quality and variety.
10. Wham! – Last Christmas
For full transparency, a few songs that will be featured here will be tracks I listened to quite often while working in retail. Indeed, the cliché that listening to Christmas music while working drains them of all their worth is a common one; it had no effect on me! “Last Christmas” is a nice fusion of pop and Christmas warmth that I never tired of, despite hearing it a billion times.
There were a couple different interpretations that were under consideration for this spot. However, the duo of George Michael and Andrew Ridgeley give it a nice gentleness that I really dig. Christmas has a number of different elements that make it eventful for any number of people—spiritual, festive, pop-ish, or somber. This kind of manages to hit all of them for me, and rather succinctly at that.
While not the most riveting tune, it’s got that “Lo-fi beats to relax/study to” aura that’s pleasurable on the ears.
9. Boys II Men – Let It Snow
Like I said before, I tried to go with a variety of tones. This particularly tone is… very horny.
Despite the departure(?) from traditional Christmas jingles, I am actually very fond of this smooth, R&B rendition of “Let It Snow.” I had not heard it prior to compiling choices for this list, nor had I heard any Boys II Men (though I did know of them). The silkiness of their voices combined with the fact that this sounds almost nothing like a “Christmas song” makes this immensely appealing.
If there’s one drawback to it, though, I feel the track goes on for a smidge too long. One could cut it at the three-minute mark and it’d be just as effective, if not more. The final minute of what’s essentially free-styling doesn’t do it as much for me. Nevertheless, this is a new addition to an already packed collection of holiday tunes I will listen to forevermore.
8. Burl Ives – A Holly Jolly Christmas
Now we’re going back—way, way back. We’ve arrived to the “classics” of yesteryear, far before I or even my mother was born. The type of Christmas music that would have this generation likely groaning in contempt.
While there are certainly older tunes I’m similarly not as fond of (I’ve found I don’t gel well with Bing Crosby—spoiler for the rest of the list, I guess), Burl Ives has a sort of “vintageness” to his voice that I find agreeable. The song itself also a sort of simplistic woodiness to it that still sounds good today. “A Holly Jolly Christmas” is like taking a pleasant hike with your buddies in the snow.
And for those not aware, if Ives’ voice sounds familiar, it’s because he was Snowman Sam in Rudolph the Red-Nosed Reindeer, that animated special our parents made us watch as kids. I didn’t even know that prior to drafting this list (even though it’s so obvious now).
7. The Ronettes – Sleigh Ride
I hope you’ve enjoyed your time in the 1960’s. We’re gonna be here just a wee bit longer.
The Ronettes is not a name familiar to me, but this classic song certainly is. What stands out about this version of “Sleigh Ride” is just how bouncy it is. Especially when the percussion comes in, it’s all that one could imagine from a song about sleigh rides. A certain pizzazz to the vocals, the beat, and the overall quality of sound is complimentary to its timeless quality.
Another track I listened to quite often in retail, this is one that seems a tad underrated in my experience. Not often do I see it brought up as among the best the season has to offer, and if so, not this particular version. Admittedly, they have good competition from Amy Grant, whose take on the song I also like quite a bit. Though it is the… attitude(?) of The Ronettes that give it the edge for me, personally.
6. Elton John – Step Into Christmas
A suggestion for those choosing to play these videos: Turn this one up. The video volume is strangely quiet. And because it’s great, but that should be apparent by it being on this list.
Funny story with this one: I had no idea it was Elton John, I had no idea it was a Christmas song (I thought the chorus was “Stand and deliver”), and I had no idea Elton John had a Christmas song. Now I know, and I’m overjoyed with finally becoming aware of it.
This is also kind of an interesting thing for me because I actually like the parts outside the chorus more than the chorus itself. Typically, people know the chorus because it’s played so much; it’s where the “good part” of songs generally linger. Here, I just like it from beginning to end, despite how much it sounds like “an Elton John song” over a Christmas classic.
The lyrics are pretty cheesy and John himself (as evidenced in the video) doesn’t seem to take the song too seriously. Really, it almost gives the song an ironic vibe to it, which is very appealing. Catchy, upbeat, and kind of dumb. I like this style of Christmas, too.
5. Nat King Cole – O Holy Night
From what I could find, Mr. King Cole has done a few versions of this song, whether solo or duets. My specific favorite is this one, presumably a remastered version off his 1960 album The Christmas Song.
I should specify for those new that I’m not a particularly religious person, though I was raised in a Christian household. Thus, there is a touch of spirituality that appeals to me, and Christmas tends to amplify that conditioned yearning out of me. “O Holy Night” is something of a difficult song to really “own,” given the necessity of a truly magnificent voice to carry it. Nat King Cole does this absolutely effortlessly.
This is another track I wasn’t familiar with before making up the Top 10. But peering around the YouTube archives for various faces associated with Christmas jingles, this man’s name came up often. This was the first song of his I listened to—it was the only one I needed to listen to. His voice is, pardon the irony, angelic. Almost anthemic in its power. Almost sobering how the tune builds into the climax of his high notes during the mid-point of the track.
Gives me chills every time.
4. Donny Hathaway – This Christmas
This is the definitive smooth Christmas song. There is no competition in my mind.
“This Christmas” is actually a song I don’t remember hearing very often in retail. What I do remember it from, though, is commercials—commercials of all things! And again, like “Step Into Christmas,” I had no idea it was a Christmas song. If nothing else, the benefit of doing this list is just discovering this “obscure” music, lost deep within the subconscious of my mind, and bringing them back to light.
This dude’s voice? Gorgeous. I want him to narrate my life through song. The track’s instrumentation? Anthemic. Really gets the juices flowing, the head bopping, the body moving. A phenomenal blend of good Christmas spirit, R&B pleasantries, and an addictive progression. You never want it to end. It may not be the most “traditional” sound, but it’s just so damn catchy that it doesn’t matter.
3. Andy Williams – The Most Wonderful Time of the Year
This song. This is one of the first songs I thought of that made me say, “Yep, immediate lock for Top 5.” When you want Christmas, you talk to Andy Williams. He’s got the goods.
When I decided to limit this list to only one artist, Williams was the main motivation as to why. I like a lot of his songs, but “The Most Wonderful Time of the Year” is his magnum opus. That voice, the instrumentation behind him; it’s practically flawless. This was my favorite Christmas song ever back when I worked retail. I got hyped every time this track started.
It’s so spirited! Williams’ voice is brilliant! It’s like a night club jazz band saying, “Christmas? Yeah, we can work with that.” I made the assertion a few times thus far that some songs are “timeless” or that they have a “vintage” feel. This song is actually timeless. It probably invented timelessness. With as much as I’m gushing, some may be shocked to know that this isn’t #1. Alas, a couple songs just do it a hair more.
2. Kelly Clarkson – Underneath the Tree
This is a straight-up pop song with Christmas bells going in the background. Only thing is that it’s a) sung by Kelly Clarkson, and b) a banger.
What’s amazing about this placement is that, if I’m remembering correctly, I do not think I’ve heard it much. Kelly Clarkson has sort of made a name for herself with Christmas albums, yet this particular song went relatively unnoticed by me. Then I made the decision to write this list. I listened to it once—once—and I’m like, “Wow, WOW—I think this might be the greatest Christmas song ever.”
Ah, well; this is #2, so not quite.
Regardless, “Underneath the Tree” has a prime benefactor in its quality due to Clarkson’s fantastic vocals. It’s kind of mind-boggling to me to hear how strongly she sings the opening chorus. Right out of the gates, it’s Christmas time. I would not have it any other way. Everything about it just hits at just the right pitch, velocity, diameter; whatever other measurement you want to throw in there. When this plays, it’s guaranteed to be a good time.
Props to her rendition of “My Grown Up Christmas List,” too, which almost made this list.
1. José Feliciano – Feliz Navidad
Do I even need to explain? Y’all know the greatest Christmas song of all time. You knew it the whole time, reader. All it took was seeing the name flash before your eyes. I know, I know; it’s a shame you didn’t immediately think of it. You’re forgiven here.
¡Feliz Navidad, mis amigos!
Honorable Mentions: Jackson 5 – Santa Claus Is Coming To Town; Bobby Helms – Jingle Bell Rock; John Lennon – Happy Xmas (War Is Over)
For other random Top 10’s, check out my blog’s list of miscellaneous Top 10’s!
What are some of your favorite Christmas songs? Is my list stupid and dumb? Let me know in the comments!
Thank you for your time. Have a wonderful timezone.