1. Run DMC “Christmas in Hollis”
This is probably my favorite Christmas song of all time. Of course, I also consider Die Hard my favorite Christmas movie. So you know, there’s that.
2. John Denver and the Muppets: “Christmas Is Coming”
Miss Piggy singing. ‘Nuff said.
3. Frank Sinatra and Bing Crosby “Jingle Bells” (a jazzy movie version)
Ol’ Blue Eyes battles Bing to see who can swing cooler on a Christmas song while they sip on some holiday punch.
4. Darth Vader Conducts Flash Mob of the “Carol of the Bells”
During winter finals or midterms, Darth Vader shows up to a library/student hall wearing a red Santa hat, and he’s there to alleviate the holiday tension of stressed-out students. He pulls out an electric guitar and leads a flash mob in a version sung in-the-round of Carol of the Bells. It’s cute like a puppy.
5. Ella Fitzgerald “Sleigh Ride”
The First Lady of Jazz bounces along with that big beautiful voice of hers, and I don’t know about you but if she asks me I’m taking a sleigh ride with Ella.
6. Mariah Carey “All I Want for Christmas is You”
Rob Fee already said it. I totally agree. This is really the only song you need for your playlist. How could we forget it if we want this playlist to be holiday proper?
7. Elvis Presley “Santa Claus Is Back in Town & Blue Christmas” (Live ’68)
Not many can follow Mariah Carey. Especially, not after that particular song. But I think Elvis in black leather snarling in his rocknroll hound-dog rhythm through Christmas songs can maybe hold the stage.
8. James Brown “Soulful Christmas”
It’s now a proven scientific fact. Few can put more soul into Christmas than James Brown. Get on up!
9. Snoop-Dogg “Santa Claus Goes Straight to the Ghetto”
Snoop did a Christmas song? Yeah! Snoop does any and every muthafuckin’ thing. You should be saying, of course, Snoop did a Christmas song. I bet it’s fucking boss.
10. James Brown “Santa Claus Goes Straight to the Ghetto (original)”
But here’s where Snoop got the idea. James Brown. Apparently, he made a lot of Christmas music. You never can tell about a country boy from Macon, Georgia.
11. Stevie Wonder “What Christmas Means to Me”
Stevie always feels good. But around the holidays, he warms rooms with his unlimited sunny good cheer.
12. Jerry Lee Lewis “White Christmas”
The Killer slays Saint Nick with this high tempo stride piano version of the classic.
13. The Beach Boys “Little Saint Nick”
To bring some of that surf city vibe up into your Christmas, it’s the boys from the beaches of Southern California.
14. Chuck Berry “Run, Rudolph, Run”
Christmas once rocked! To prove it, Chuck Berry’s gonna duckwalk all over your day.
14. John Lennon “Happy Christmas (War is Over)”
This song is the “Imagine” of Christmas music.
15. Simon and Garfunkel “Comfort & Joy”
These sweet-voiced sensitive lads really put something angelic in the air with this one.
16. Wham! “Last Christmas”
Then there was these two lads, and the ‘80s Pop world they came from… well, they had this to offer to the canon of Christmas music. Seems kinda perfect.
17. Stevie Wonder “Someday at Christmas”
Just let Stevie warm it back up and smooth it out with some Christmas soul and sunny day Stevie Wonder goodness.
18. Otis Redding “White Christmas”
Another take on this holiday classic. I’m trying so hard to not say listen to Otis put some blackness into “White Christmas”… Damnit! I said it!
19. The Sex Pistols “Punk Rock Christmas”
You know we (okay, me… I) had to have a little punk rock… and who better to bastardize a Christmas song than Johnny Rotten?
20. U2 “Christmas (Baby Come Home)”
Some folks traditionally enjoy a Christmas ham. Well, here you go. Bono.
21. Sinead O’Connor “Silent Night”
Keeping it Irish for a moment, I don’t know if she recorded this back when she had a head that looked like a snowball, but either way, her voice is rad. Pristine.
22. Band-Aid “Do They Know It’s Christmas”
This is the other great addition from the ‘80s, given to the Christmas music canon by celebrities of the day. It’s always good for a laugh. You’re welcome, world!
23. Gene Autry “Here Comes Santa Claus”
Written and performed by the singing cowboy himself, this song’s another one you kinda just have to include. It’s so jangly!
24. Otis Redding “Merry Christmas, Baby”
Otis sweats soul. Even when it’s cold outside, Otis is in here sweating Christmas soul for you.
25. Frank Sinatra “The Christmas Waltz”
We had to go out with a classic. So hand the mic over to Ol’ Blue Eyes and he’ll keep it classy, Saint Nick.
KWANZAA BONUS: Elvis Christmas Album (The Full Album)
Maybe you and your roommate, or you and your friends, might get a grin from this one, or maybe you work in the sort office where folks might appreciate this lushness:a full length Elvis Christmas Album. But consider this Elvis like a Kwanzaa present. Seems kinda fitting.