As before, plus:
'So Much Wine' (The Handsome Family) - I can't believe I forgot this one, as any song that begins 'I had nothing to say on Christmas day, when you threw all your clothes in the snow' deserves pride of place on anybody's Christmas album. It's got that Del Amitri-esque trick of balancing lyrics of relentless despair with a chirpy tune, too ('Listen to me, butterfly: there is only so much wine you can drink in one life, but it will never be enough to save you from the bottom of your glass'), which would surely fit somebody's Christmas, but I was just listening to it while reading a blog post on the MLA convention, which gave it a whole new twist. Good luck, brave souls.
'When The Water Gets Cold And Freezes On The Lake' (Herman Dune) - Herman Dune are a French band my brother's crazy about, but I could take them or leave them, this song excepted. Good breakup songs are difficult to pull off this simply ('I love the smell of your hair and the blue of your eyes / But you're far too complicated, and you tell a lot of lies'), and the return to a freezing lake as a point of resolution is something sharp. This should be the other bookend of a mix CD that begins with Joni Mitchell's 'River'.
'Christmas In Washington' (Steve Earle) - which has very little to do with Christmas or winter or anything related, really, but earns its way onto every such playlist simply by virtue of being really, really good.
'Through December' (Laura Viers) - Haunting, mournful, sounds like the concept of 'bleak' set to music, but it's gorgeous. (On a related note, I had this playing on repeat when I was marking my last batch of undergraduate essays.)
'Christmas In Nevada' (Willard Grant Conspiracy) - I can't, by any rhetorical charades, make the lyrics here look like anything festive, but I can say that it's so musically upbeat that by the time the singer hits 'I'll take my pay and buy a gun / Steal a car and hope it runs / Find a place to make my name', it's up there with 'God bless us, every one!'
As before, plus: