Holiday music playlist (indie/alternative/classic rock)?

Schedryk
Fairytale of New York – The Pogues
Suzy Snowflake – Soul Coughing (or, if you’re more traditional, Rosemary Clooney)
Peace on Earth – David Bowie/Bing Crosby

Those are just a couple of the more.. eclectic… songs that I must have on my holiday playlists.

I am also a sucker for goofy songs, like Dominic the Donkey, but that may be pushing it. :)

The Waitresses—Christmas Wrapping
The Kinks—Father Christmas
U2—It’s Christmas (Baby Please Come Home)
The Pretenders—2000 Miles

The Weepies—All That I Want
The Bird and the Bee—Carol of the Bells
Death Cab For Cutie—Christmas (Baby Please Come Home)
Zooey Deschanel and Leon Redbone—Baby, It’s Cold Outside
Tom Petty and the Heartbreakers—Christmas All Over Again
Barenaked Ladies—Green Christmas

This is the best rendition of Jingle Bells I have ever heard.

Playlist to follow.

I love the Phil Spector Christmas Album and Brenda Lee’s rockin around the Christmas tree is great too.

booo this q needs @jeffgoldblummsprivates thee wizard i miss him

Lots of great new items for the list! Thanks. Keep ‘em coming.

I love love love Brian Setzer’s Christmas albums Boogie Woogie Christmas and Dig That Crazy Christmas. Big-band, swing style – you can’t go wrong.
Also, I agree with @lonelydragon regarding Barenaked for the Holidays and Zooey Deschanel’s version of “Baby, It’s Cold Outside”... or Zooey’s version of anything, really.
There are also some fun renditions of classic Christmas songs on Bette Midler’s Cool Yule.

“Christmas is Going to the Dogs” by the Eels
“Last Christmas” by Jimmy Eat World
“Just Like Christmas” by Low
“The Christmas Song” by The Raveonettes

Those are a few off the OC Christmas soundtrack. But my all-time favorite is “Three Ships” by Sting.