Have you ever gone and looked through the holiday albums on iTunes? I think the best word is “disturbing”. There’s something called “The Ultimate Christmas Album” with everyone from Randy Travis to Elvis to Wham! to Gary Glitter to Bing Crosby, to Gloria Estefan, Weird Al Yankovic, and ABBA.. Bob Dylan now has a Christmas album. (Presumably his Zimmerman grandparents are rolling in their graves, if they haven’t worn to a nub already.) If you ever wanted to hear Dylan singing Buffet, this is your chance, since it’s got “Christmas Island”. Johnny Cash has three, from 1963, 1980, and 2003; you can just hear his voice disintegrating or being honed to its essence, however you want to think of it. Andrea Bocelli has a collaboration with the Mormon Tabernacle Choir immediately followed by a duet with Mary J. Blige, and three songs after that he’s singing with the Muppets.
I do like the review of “James Taylor at Christmas” that calls the album “as inoffensive a collection of seasonal classics as one could hope for … makes absolutely no impression on the listener.”
I go back and forth about Johnny Cash, young Cash was far more melodic, but the elder version had grit and heart. But since I like his story songs best of all, it’s rather moot. Since the story songs are spoken/chanted more than they are sung.
There’s an interesting article in the Times I think you’ll enjoy. Along the line of Dylan and Christmas songs.
http://www.nytimes.com/2009/12/18/opinion/18feinstein.html?_r=1&scp=1&sq=whose%20christmas&st=cse