I try not to bust out the Christmas music too early in the year, but now that we're past Thanksgiving and into December I think it's acceptable. My favorite holiday listening pleasures in recent years have included Ella [Fitzgerald] Wishes You a Swinging Christmas and Starbucks High-Fidelity Holiday. Charles got me the latter several years ago because it has a great Cocteau Twins version of "Winter Wonderland", but I also love Keb' Mo's "Jingle Bell Jamboree", Dean Martin's "Baby It's Cold Outside" and Robbie Robertson's "Christmas Must Be Tonight." That last one always brings tears to my eyes. I have no idea why.
But I think one of my all-time Christmas favorites has to be the Pogues' and Kirsty MacColl's "Fairytale of New York (Christmas in the Drunk Tank)". It's not the most uplifting of Christmas tunes, but it's one hell of a great song. RIP Kirsty.