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A Definitive Ranking Of The 25 Best Holiday Songs Ever Recorded

Photo credit: Boglarka Bodnar/Associated Press
Photo credit: Boglarka Bodnar/Associated Press

Two years ago, we scientifically ranked every Christmas song. That remains a helpful reference, but it’s not a ranking of holiday song recordings. Here, then, is a ranking of the top 25 seasonal songs ever recorded, and it is not debatable because it is 100% accurate. (A Spotify playlist featuring most of the songs on this list is available here, and is embedded at the bottom of this post.)

25. Danny Elfman — “Town Meeting Song”

We start our list with the best song from the best Christmas movie ever made. (We’re passing on the Die Hard question and Love Actually can eat shit.)

24. Louis Prima — “What Will Santa Claus Say? (When He Finds Everybody Swinging)

There’s a reason some holiday standards are standards. A number of them show up further down the list.

23. The Waitresses — “Christmas Wrapping”

This song’s seen a resurgence in the past few years, but it’s still one of the most underplayed holiday tracks.

22. Cracker — “Merry Christmas Emily”

Fun fact! The best holiday songs don’t appear on holiday-themed albums. This one’s from Cracker’s 2002 record Forever.


21. Deja Voodoo — “Bottlestore Galactica Xmas Special”

This track is from a New Zealand-only compilation titled Christmas On The Rocks. I don’t know why I own a copy, as I can barely find any reference to it at all on the Internet.

20. Kay Starr — “(Everybody’s Waiting For) The Man With The Bag”

Again, there is a reason this song is currently playing in every Macy’s across the United States.

19. Count Floyd — “Reggae Christmas Eve In Transylvania”

Count Floyd was an SCTV character, the one who wasn’t Guy Caballero. Leave it to Canadians to find the true meaning of Christmas.

18. Louis Armstrong — “Cool Yule”

This song is aspirational, insofar as you will never be as hip as anyone involved in this recording, but you can try!

17. “Weird” Al Yankovic — “The Night Santa Went Crazy”

“Merry Christmas to all, now you’re all gonna die!” Can anything capture the spirit of the season better?

16. June Christy — “The Merriest”

Here’s a reminder that back in 1961, pop music could sound weird, atonal, and in irregular meter.

15. Squirrel Nut Zippers — “Santa Claus Is Smoking Reefer”

Somebody bet Squirrel Nut Zippers they couldn’t record the worst Christmas song ever. But Squirrel Nut Zippers were so awful, they accidentally recorded the 15th-best Christmas song ever.

14. Dean Martin — “I’ve Got My Love To Keep Me Warm”

The more popular Dino choice this time of year is the capital-P Problematic “Baby, It’s Cold Outside.” But “I’ve Got My Love To Keep Me Warm” has a lot more of what made Dean Martin such a perfect personality. Also, Dean Martin died on Christmas. If Hell is a never-ending karaoke night, as many of the demons who haunt my dreams report, I’ll sing this tune for eternity.

13. Wesley Willis — “Merry Christmas”

Yes, there was an official video for this song.

12. Ralph Marterie & His Orchestra — “Dig That Crazy Santa Claus”

Something lacking in modern pop music is the attempt to tie the holidays into contemporary trends and lingo. You see this throughout some of the standards—see #24 above, too—and we’re all worse off for lack of songs about Santa Claus being hyphy or dropping the NaeNae.

11. Da Yoopers — “Rusty Chevrolet”

This also, inexplicably, has an official video. (That this didn’t make the top ten is a tragedy, but there really are ten better holiday songs!)

10. Tom Waits — “Christmas Card From A Hooker In Minneapolis”

The Neko Case version is probably better, but you can argue about that in the comments.

9. The Blind Boys Of Alabama — “Last Month Of The Year”

Jesus was not, actually, born in the last month of the year, but this song is far from the most egregious offender of this misunderstanding of history. That title goes to “The Snow Lay On The Ground,” which not only gets the date wrong but claims it was snowing in Bethlehem—a particularly rare event, even in December (which is not when Jesus was born).

8. Benny Goodman — “Santa Claus Came In The Spring”

Here we have Santa actually arriving at a more appropriate historical time for the Savior’s birth, though the narrator of this track seems to be experiencing a particularly vivid opium dream.

7. Les Brown & His Band Of Renown — “Let It Snow! Let It Snow! Let It Snow!”

Like some of the above tracks, this one’s a standard for good reason.

6. Dar Williams — “The Christians And The Pagans”

A fine allegory for your Trump-voting relatives. (We recorded a version about Bernie Kosar & Boomer Esiason ten years ago.)

5. Peggy Lee — “Ring Those Christmas Bells”

Another undisputed classic, even though the lyrics are sub-Wiggles quality. (Our K7 remix is... a thing that exists.)

4. James Brown — “Hey America”

AHH NO! TOO FUNKY! (It also briefly and inexplicably breaks into Hava Nagila.)

3. Kevin Bloody Wilson — “Hey Santa Claus You Cunt”

I understand at least half the words in this song.

2. Ben Folds — “Lonely Christmas Eve”

These lists almost always include “You’re A Mean One, Mr. Grinch” which is unfortunate as that song reeks of anti-Grinch bigotry. Here’s a version much more sympathetic to the green-hued creature. It would be the best holiday song ever recorded, except for its association with the very bad 2000 film version.

1. Andy Dick & The Bitches Of The Century — “Santa’s Yule Log”

Across the country, families gather around the fireplace to sing this touching tale of a boy meeting Santa. It’s the Reason For The Season.

Timothy Burke is formerly Deadspin's Video Director.