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 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
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.