Tom Pacheco's Christmas on Times Square (Jimmy the Fiddler) to be found on Woodstock Winter or Swallowed up in the Great American Heartland, is a heart rending song. Both albums are still available.

Loudon Wainwright's Christmas Morning from Social Studies is shocking. I was dumbstruck when I first heard it.

Fairy Tale in New York still packs a punch despite being belovrd of the Christmas compilation album compilers.

On the traditional front, The Mistletoe Bough which recalls the oft told tale of a bride getting locked in a trunk during a game of Hide and Seek, is pretty hard hitting too. The version I know is on Calennig's excellent A Gower Garland.