The 15 Coolest Holiday Songs

This is not the 20 best known songs, nor is it the 20 most musical. These are just the coolest holiday songs that should be on everybody’s playlist. Yes most of them are old, that is because to us something has to stand the test of time to be considered cool.

15. Leon Redbone and Dr. John – Frosty The Snowman

Just two of the coolest motherfuckers on the planet (three if you count Frosty)

14. Paul McCartney and Wings – Wonderful Christmas Time

Nobody does the trippy, easy listening, rhythm change combo like Paul.

13. Dean Martin and Frank Sinatra – Marshmallow World

Three words: Dean and Frank

12. Christina Auguilera and Dr. John – Merry Christmas Baby

Dr. John makes his second appearance and young Christina is just absolute fire here.

11. The Ramones – Merry Christmas (I Don’t Want To Fight Tonight)

You could be making any list of any cool things ever and it would have to include The Ramones.

10. The Brian Setzer Orchestra – Zat You Santa Claus?

Quite a few people have done this song well but Brian Setzer does it as good as any of them.

9. Bing Crosby and David Bowie – The Little Drummer Boy/Peace on Earth

An odd couple that mesh surprisingly well.

8. Adam Sandler – Hannukkah Song

Remember when Adam Sandler was cool? That was awesome.

7. The Beach Boys – Little Saint Nick

A Christmas surf song? Sure, why not?

6. Bruce Springsteen – Santa Claus Is Coming To Town


5. Nat King Cole and Frank Sinatra – The Christmas Song

Nat King Cole is imperative on a Christmas song list, and Frank should always be mentioned at least twice.

4. John Lennon – Happy XMas (War Is Over)

Only man to ever live who could turn a Christmas song into a protest song and not be annoying about it.

3. Run DMC – Christmas In Hollis

Go ahead and try to listen to this without bobbing your head.

2. The Jackson 5 – Up On The House Top

Does this really need an explanation?

1. The Pogues featuring Kirsty MacColl – Fairytale Of New York

A Christmas song about drinking, jail, and love that sours over the winter. It doesn’t get more Real Cape than that.

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