My two favorite remain John Prine and Leon Redbone. After you hear Redbone do White Christmas, Bing sounds hyper. His rendition of Christmas Island is great too. Prine not only sings, but tells great stories.
Venom: "Black Christmas" -only one song, but I play it every year on Christmas Eve to celebrate the season!
also, there's a great Xmas collection from Esquivel (50's lounge orchestra hero) if you're a fan of "zoo-zoo" lyrics and early synths like the annoyovox and the irritatophone.
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