The Definitive List of the Best VERSIONS of Popular Christmas Songs

Illustration by Phil Scroggs

Everybody has their favorite holiday song. With so many recordings and re-recordings to choose from, top 10 lists are as abundant and diverse as December snowflakes. But I’ve got a different take on the topic. Here is my ultimate list of the best versions of the best Christmas and seasonal songs. Some cover versions improve upon the original. Others, we could do without. Don’t get me wrong — Harry Connick can sing the hell out of Jingle Bells. But, we don’t need any more reimaginings of that old tune. It’s been done enough, and it’s probably not going to get any better.

Some recordings are so iconic that only one version comes to mind when you hear the title. Or could it be that only one version gets the most radio plays? I’ll omit the obvious classics. Elvis is the only guy who can sing Blue Christmas. Bing Crosby is synonymous with White Christmas. “Band Aid” is not only the best sterile adhesive owie strip for me — but it’s also the only group of washed-up 80s singers who should ever sing “Do they know it’s Christmas.” I’m brand-loyal like that.

Most of the songs on my list were recorded before I was born. But, I’m perfectly fine with more contemporary artists writing and recording new original seasonal songs. Mariah Carey hit the jackpot with “All I Want for Christmas is You” in 1994. But, we don’t need a Bieberized version of “Deck the Halls.” And nobody’s clamoring to hear Bey’s rendition of “Santa Claus is Coming to Town.” Bruce Springsteen’s is the only version of that tune I ever need to hear again, forever. Thanks, Boss.

So, to kick things off, I’ll start with the granddaddy of them all.

1. The Christmas Song — Nat King Cole
When it comes to titles, you can’t get any more straightforward than this one. And the only guy who should ever sing it is Nat King Cole. When I hear his 1961 recording, it reminds of me of the annual Christmas Eve party we would attend when I was a kid. Our neighbor, Dr. Bill, would put Cole’s Christmas album on to create the perfect party soundtrack. This song was written in 1945 by Mel Tormé when he was just 19 years old.

2. Merry Christmas, Baby — Lou Rawls
There are lots of versions of this 1967 tune. But, the best one is by Lou Rawls. The horns on this track swing like hell. And Lou’s raspy voice is perfect. The song is slow and bluesy, but it makes you grin and groove. This song has a strange feature — a few bars of “Jingle Bells” during the musical intro. I don’t know what it’s doing there, but it works.

3. Christmas Baby (Please Come Home) — Darlene Love
U2 made a great cover of this song. But, it’s only a runner-up to the original by Darlene Love from 1963. Produced by Phil Spector, this tune was kept alive in my mind thanks to Darlene’s annual appearance on the Letterman show where she would join the house band and blow the roof off the Ed Sullivan Theater.

5. Zat you, Santa Claus? — Louis Armstrong
The Louis Armstrong recording of this song puts all others to shame. I’m still trying to forget that I ever heard of the one by Buster Poindexter. Louis and Ella Fitzgerald have some of the best Christmas music out there. Check out “Ella wishes you a swinging Christmas” from 1960.

6. Santa Baby — Eartha Kitt
This one should only ever be sung by a sultry chanteuse. And the best of those has got to be Catwoman herself, Eartha Kitt. Every verse is sung with a purr as Eartha extols the virtues of Christmas commercialism. Go listen to this song right meow!

7. You’re a Mean One, Mr. Grinch — Thurl Ravenscroft
Here’s another classic. And there’s only one guy in the world who can sing it. Thurl Ravenscroft. “WHO,” you ask? You may not recognize the name — but you do know the voice. Not only did he record the original (and best) version of this song, but he was also the voice of Tony the Tiger (of Frosted Flakes fame). Thankfully, there aren’t many covers of this one to compete with Thurl’s original. But, the second best version of this is one you’ve never heard. My favorite band in college was a group of friends who called themselves “La Brea Stompers.” And when they would break out their version of the Grinch song each December, it was always a crowd favorite.

8. Have yourself a Merry Little Christmas — Judy Garland
This song has been turned into a more cheery, upbeat tune since the original came out. And those versions are fine. But, to hear it the way it was meant to be sung, check out Judy Garland’s performance in the 1944 movie “Meet me in St. Louis.” If you’re not bawling your damn eyes out by the end, you ain’t got a heart. The original song was even more of a downer. But Garland convinced the writer to brighten it up before she recorded it. And the result perfectly captures the bittersweetness of the season.

9. Happy Christmas (War is Over) — John Lennon
For my money, John Lennon is the only one I want to hear singing this tune. The song is great and has held up quite well since 1971. Adults and children from the Harlem Community Choir add a great touch that helps make up for Yoko’s um,… vocalizations.

10. (Peace on Earth/) Little Drummer Boy — Bing Crosby & David Bowie
When it comes to my favorite Christmas songs, I’m more about the HOLLY than the holy. But, I’ll make a special exception for this last one. And the video for this song is what seals it. When Bing Crosby’s new neighbor Davie Bowie dropped by to croon with him in 1977, it certified this version as the best. The video is so awkwardly cheesy and awesome. There’s even a shot-for-shot re-make of the surreal video starring John C. Reilly and Will Farrell.

Lesser-known Christmas songs

Now it’s time for a few quick deep cuts. These are some lesser-known Christmas songs that I think everyone should hear. The greatest remake that you’ve never heard of is by Barenaked Ladies. It’s their a capella version of “Deck the Halls.” But it’s been retitled “Deck the Stills.” The tune is the same. But, instead of the expected lyrics, the guys substitute the words “Crosby, Stills, Nash, and Young” for the entirety of the song. If you’ve got a spare 32 seconds, you should give it a listen. It fits the BNL style and is funny the first time or two that you hear it. But, I think the chances of it becoming a perennial favorite are pretty slim.

Here’s another obscure one. It’s a mashup of “Rudolph the red-nosed reindeer” to the tune of “Roxanne” by The Police. The animation editing and song arrangement are pretty genius. Even the singing style is reminiscent of the music from those old Rankin and Bass animated TV specials.

Many of my favorite Christmas songs are ones that don’t get a ton of radio play. And maybe that’s why I like them so much. For example, “2000 Miles” by The Pretenders is a solid pick. It’s not over-the-top Christmassy. Its melancholy theme is a nice balance to the perky happy theme of other holiday tunes.

Another great one is “Fairytale of New York” by The Pogues. (Featuring Kristin MacColl) I think it’s the only Christmas song that contains words you can’t say on network TV.

Also, check out:
“Go Power at Christmas Time” by James Brown and “Slick Nick, You Devil You” by Fishbone.

A newer holiday tune that I love is by the French band Phoenix. “Alone on Christmas Day” is from the 2015 Netflix special “A Very Murray Christmas.”

In closing, here are some Christmas songs I never need to hear again:

Grandma Got Run Over by a Reindeer
All I Want for Christmas — by Spike Jones
I Want a Hippopotamus for Christmas — by Gayla Peevey

What’s on your list? Leave a comment if you’ve got a favorite cover song I left out.

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