My favorite Christmas songs, categorized and kinda ranked
It's the Most Wonderful Time of the Year...will not make this list, but I agree with the sentiment.
In a recent Weekender, I shared my Starting Five Christmas Songs from a past holiday episode of The Stretch Four podcast 1. I stand by my attempt to create a basketball-style roster of songs where each slot fills a particular role based on the corresponding bball position. It holds up as a great representation of my taste in Christmas Music, but is a bit limited by the (very creative and fun) format that we created for the pod.
So I’m here to get cheeks-deep 2 into the Holiday Spirit and share my favorite Holiday songs, separated into categories based on how I think about Christmas/Holiday/Seasonal music.
Here’s what I mean. I could just do a list of my 25 Favorite Christmas Songs, or whatever, but instead I’m giving you a deeper look into my brain by listing the songs based on what kind of playlist I’d put them on. Here are the categories:
Traditional/Religious
Does the song hyper-focus on Baby Jesus? Are you falling on your knees at the presence of angels? Would you sing it in church? It belongs here.
Standards
These are songs that, if you were going to make a Christmas Album, you’d think about covering. Classics that are less focused on the religious part of the season. Songs that I would consider not belonging to anybody in particular, and everybody might have a different favorite version by a different artist.
Originals
These are songs that, if you covered them, one 3 might ask, “Why?” They are so singularly identified as belonging to the person who created them that there’s no need for anybody to create a new version, in my mind, at least.
Alt X-Mas
Songs that buck the tradition in one way or another. Whether they rock super hard, or are a little bit silly (but not too silly, that comes next), or a lot of bit funky, or look at the season from a new perspective. There’s a thin line between this and “Originals” in some cases, but I’m just gonna go with my gut as to where I feel like the song belongs.
Novelty/Kids
Songs for children. Good thing that at the holidays, kids can be anywhere from one to 92 (sorry 93-year-olds, you’ve aged out of kiddom.)
Instrumentals
Because why not.
I’m not going to put any arbitrary rules here where I limit the number of songs per artist; I’m just going to blurt out my favs. I also started out trying to rank them, but then the more songs I remembered and the longer these lists grew I didn’t want to nitpick over the nuance of what my 7th favorite and 8th favorite Original Christmas songs were. 4 I didn’t even keep the same number of songs in each category, I just went as long as I could confidently say that these were my favorite songs.
Okay, now that you know the rules that I made up on the fly, let’s get into the lists!
Traditional/Religious
Peace on Earth/Little Drummer Boy - Bing Crosby & David Bowie
This is slightly a cheat of a pick because while The Little Drummer Boy is indeed a religious song that is mostly about the Baby Jesus, the Peace on Earth part would fall under “Originals,” but whatever, this is my list, so it’s my favorite.
The Bells of St. Mary - Bob B. Soxx & The Blue Jeans
The power of the wall of sound is on full display here, knocking my dang socks off. It’s a rocking version of a more traditional song, and sometimes that just elevates it to new heights…
O Come All Ye Faithful - Nat “King” Cole
…and sometimes “traditional traditional” is the way to go. It’s going to be really hard not to put almost every song from this album on this list. I will try to exhibit some restraint.
Do You Hear What I Hear? - Whitney Houston
I hear a G.D. banger, that’s what I hear.
Silent Night - The Temptations
Just close your eyes and feel this one from the bottom of your soul.
O Holy Night - Celine Dion
I chose Celine’s version of this song because I think it strikes the right balance of a slightly haunting but sweet beginning, building up to a powerful crescendo. Josh Groban’s version is the churchiest, Mariah Carey’s is injected with a shot of pop music flair, and Nat “King” Cole’s version is fantastic, 5 and while relistening to it (right now as I write this) it’s hard not to actually pick his version, but I’m gonna stick with Celine. I feel pretty good about that choice now that ol’ King Cole is done singing because I don’t think he sticks the landing as powerfully as the Canadian Queen.
Standards
The Christmas Song - Nat “King” Cole
There’s no better name for this song. You can call it “Chestnuts Roasting on an Open Fire” if you want, or even its official parenthetical name “(Merry Christmas to You),” but this is just “The” Christmas Song. It’s three minutes of pure seasonal joy, warms me up from the inside out like a bowl of soup after coming in from the cold.
Have Yourself a Merry Little Christmas - Frank Sinatra
Along with The Christmas Song, this one hits me the most in my heart. It’s a little bit sad and sentimental, which is how Christmas feels to me. There’s no wrong way to list your favorite Christmas songs, and I think everybody’s list is connected with their memories and feelings about the holidays. I think of Christmas as cozy and warm, but there’s also a tinge of sadness — from a mix of nostalgia and remembering loved ones who aren’t with us anymore, and partly just because I’m no longer literally a child. 6 While Judy Garland’s version is the original, it drags a bit too much for it to be my favorite version. Frank hits the sweet spot and, of course, his voice is just butter.
Sleigh Ride - The Ronettes
The “Ring-a-ling-a-ling-a-ding-dong-ding” in the background is one of the things in this world that brings me the most joy.
White Christmas - Otis Redding
Good lord.
White Christmas - The Drifters
Sure, Bing’s version is the original, but Otis Redding and The Drifters versions are my favorites. It’s probably because Otis Redding is the man and the Drifters’ version is connected to its use in Home Alone, but it’s also livelier, more fun, and doesn’t make me feel a little bit like I’m celebrating some kind of wink-and-a-nudge racism.
Ray Charles - Winter Wonderland
The way he hits the three syllables in “beautiful” would land this song somewhere on this list alone. This song sounds like the coolest frolic of all time.
Let it Snow! Let it Snow! Let it Snow! - Dean Martin
Jaunty and fun, and when it comes to jaunty and fun, Dean Martin is the go-to guy. I thought about having another category here of “Wintery Tunes” that aren’t technically about Christmas but are seasonal, but I decided to just keep those kind of songs here.
It’s Beginning to Look a Lot Like Christmas - Bing Crosby
Here you go, Bing. You can have this spot.
Jingle Bell Rock - Bobby Helms
I view this song as sort of a companion piece to the (in my opinion) superior '“Rockin’ Around the Christmas Tree.” The guitar on this song is pure ‘50s rockabilly Christmas joy.
I’ve Got My Love to Keep Me Warm - Ella Fitzgerald, Louis Armstrong
What a team. The piano dances around and their voices just sound so good together.
A Holly Jolly Christmas - Burl Ives
A goofball of a song. But I’m a goofball and I love goofball things.
(There’s No Place Like) Home for the Holidays - Perry Como
If a song is about home and also about Pennsylvania, you got me, I’m your sucker. Como’s corniness only adds to the enjoyment here for me.
Originals
Christmas (Baby Please Come Home) - Darlene Love
I think it’s the GOAT Christmas song. It’s either this or “The Christmas Song”, please don’t make me think too much about it and pick. If you have a spare two hours, you should watch this compilation of Love singing the song on Late Night with David Letterman throughout the years (tip of the hat to Luke Giordano for putting me on to this beauty of a collection).
Merry Christmas Baby - Otis Redding
Good lord.
Okay I’ll say more this time. Otis Redding is my choice for frontman in any hypothetical “build a band” draft. I don’t think he’s my favorite voice of all time (that would be Sam Cooke) but he’s near the very top of my list. Sort of breaking a rule here regarding how songs in this category are uncoverable because Bruce Springsteen’s version gets a pass.
This Christmas - Donny Hathaway
A groove and a bop. I thought about including this on the “Alt X-Mas” list because it’s almost more of just an R&B love song than it is a pure Christmas song, but it’s Christmasy enough to make it here.
Rockin’ Around the Christmas Tree - Brenda Lee
This song is the equivalent of getting the perfect amount of tipsy, where you feel great and are loose and having the most fun, but you don’t have to worry about being hungover or doing something stupid that you’ll regret. The kind of drunk that if alcohol weren’t an addictive poison, I would want to feel like all the time. I mean, I still kind of want to feel like that all the time, but I can’t do it with alcohol; that would be bad. Good thing this song exists.
All I Want for Christmas is You - Mariah Carey
I couldn’t put this any lower on the list. It’s the musical equivalent of an adrenaline shot to the heart. But of happiness and joy.
What Christmas Means to Me - Stevie Wonder
Stevie kind of just lists a bunch of Christmas stuff and it works. It really warms my heart while also serving as a checklist of what I need to prepare for the season. My one knock with this song, and it isn’t really a knock on this song (but I think mentally affects my enjoyment of it, unless I catch it and say “knock that off”) is that a lot of modern, pop, original Christmas songs try to sound like it — while also trying be so bland and boring that Target will pick them up to put into one of their commercials. That’s not this song’s fault at all though. This song rules. Those other ones can kick rock.
I also love Stevie’s “Someday at Christmas” but its hopeful message of one day having peace has been making me too sad lately. I think its something about the fact that the song is almost 60 years old and his “maybe not in time for you and me” lyric is still hauntingly relevant and I can’t sing along to the song while in the vacinity of my baby without getting a terrible ache in my heart.
Happy Xmas (War is Over) - John Lennon, Yoko Ono
Speaking of a hopeful message of one day having peace on Christmas…for some reason this one doesn’t make me quite as sad as when Stevie reminds us that our lifetime may be filled with war.
Wonderful Christmastime - Paul McCartney
This song gets way too much shit. It makes me happy and I truly love the message of just having a simple, wonderful Christmastime. It doesn’t have to be anything more than that.
It also serves as a nice counter to the very serious protest song from Lennon, like the two of them really leaned in their own directions after their split and nowhere is it more obvious than in their Christmas songs.
Merry Christmas, Happy Holidays - *NSYNC
I unironically love this song and will (and have) danced in the aisles when it comes on in Target. 7 I feel like stopping after mentioning this song is a good place because including it means I’m heading into wacky land but also stopping here feels bad because including this and leaving other stuff off feels wrong.
Alt X-Mas
Run Rudolph Run - Chuck Berry
“All I want for Christmas is a rock ‘n roll electric guitar.” Hell yeah, now I do.
Fairytale of New York - The Pogues
I can see a better time, when all our dreams come true.
Oh, fuck, I’m crying again.
Father Christmas - The Kinks
The Kinks are on my short list of favorite bands, and a song about robbing rich people (and also Santa Claus?) at Christmas time as dirty little poor (British) street urchins rules so fucking hard.
Christmas Time Again - Tom Petty
This is the best contemporary Christmas song when bopping around in a Christmas rush. A lot of people love The Waitresses Christmas Wrapping, but it never hit for me because of how negative it is about Christmastime. Tom Petty loves that it’s Christmastime, and so do I.
Just Another Christmas Song (This Time I’ll Sing Along) - Sharon Jones & The Dap Kings
The title of this song is a lie. It is in no way “just another” Christmas song.
Christmas Will Really Be Christmas - Lou Rawls
The horns are too damn filthy to put this on “the originals” list. This grooves too hard, I have to put it here.
Merry Xmas Everybody - Slade
This song aggressively wants everybody to have a Merry Xmas. It’s in your face about it. “Everybody’s having fun” sounds less like a declaration and more like a threat, but I’m here for it.
Merry Christmas (I Don’t Want to Fight Tonight) - The Ramones
My family used to get into fights in the car on the way to most major holiday celebrations so this one really hits for me.
Christmas is the Time to Say “I Love You” - Billy Squire
This song sounds like putting your arm around friends in a boozy, end-of-the-night singing circle. That, as much as childhood joy, is a big part of Christmas and how the Christmas season should feel.
Little Saint Nick - The Beach Boys
Surf music about Christmas!
Christmas in Hollis - Run DMC
“Don’t you have any Christmas music?”
“This is Christmas music!”
Please Come Home for Christmas - Eagles
It’s the only Eagles song I can stand.
Novelty/Kids
It Feels Like Christmas - Ghost of Christmas Present - Muppets Christmas Carol
This song makes me weep like a little baby, every time I hear it. I probably listen to this song less often than I want to, just because I don’t want to tear up while I’m driving and be a danger to myself and others on the road. “It’s true wherever you find love, it feels like Christmas” is an all-timer of a line. Oh, my heart!
Frosty the Snowman - The Ronettes
I wonder what Gene Autry did the first time he heard this version.
You’re a Mean One, Mr. Grinch - Thurl Ravenscroft
For more about my thoughts on this song, read this piece.
A way-too-far deep dive into my favorite lyric in the song 'You're a Mean One Mr. Grinch"
Santa Claus is Comin’ to Town - Bruce Springsteen
Santa Claus is Comin’ to Town - The Jackson Five
More Gene Autry covers that take the singing cowboy’s originals to another level. I couldn’t just pick one version here. They’re each great in their own way. Slight nod to Springsteen’s live version because of how fun it sounds to be at that concert.
Welcome Christmas - Dr. Seuss’ How the Grinch Stole Christmas
Then the Grinch thought of something he hadn't before. Maybe Christmas, he thought, doesn't come from a store. Maybe Christmas, perhaps, means a little bit more.
Up On The House Top - Gene Autry
This was my favorite of the kids Christmas songs when I was a kid, and that should count for something on this list.
Instrumental
Somewhere in my Memory - John Williams
This song is just pure magic. And so is Home Alone.
The Entire Vince Guaraldi Trio Charlie Brown Christmas & Oscar Peterson’s An Oscar Peterson Chrismas albums
I just had to put these entire albums on as faves and call it a day here. The deeper I dove into Christmas music the more songs I didn’t want to leave out here. I just love Christmas music way too much. I probably forgot a lot of stuff. I’m tired. Doing this list was a bad idea.
Did I leave something off that you’re mad about? Mention it and I’ll tell you my thoughts about it. Maybe it slipped my mind but maybe there’s a reason why I left it off. Wouldn’t you like to know?
1 Which is on a break for now until I figure out my schedule with a baby. WE WILL RETURN!
2 Face cheeks, not butt-cheeks. That’s how deep!
3 The “one” in this situation is me, I guess, because it’s my list and my opinions.”
4 I’m not a music journalist, I’m just a guy having fun writing about Christmas music..
5 As is his entire Christmas album.
6 But will always be somewhat figuratively a child.
7 Playing IN a Target is much different than playing in a Target COMMERCIAL.
Sign up for my mailing list to get weekly emails with new comedy content, updates, and more!
Support my comedy and get members-only exclusive content here on my website, or with a paid subscription through Substack or Patreon. You can also send a one-time tip through Venmo.
