39. Aimee Mann, 'One More Drifter in the Snow'
For all its loving invocation of snow and mistletoe, "I'll Be Home for Christmas" is one of the saddest Christmas songs ever. The kicker is in the final lyric: "if only in my dreams." Naturally, it's the centerpiece of this forlorn 2006 album by Aimee Mann, where she kicks off with "Whatever Happened to Christmas?" and makes the notion of walking in a winter wonderland sound lonely and cold. This isn't a cup of holiday cheer – it's the bracing chaser.