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I must also go with Vince Guaraldi. Classic for folks my age.
However, December by George Winston is also one of my seasonal favorites. And I've somehow just gotten to
love the song "It Snowed (Last Night)" by Meaghan Smith, which was on an iTunes holiday sampler a couple years ago. So upbeat and cheery about snow, it could only have been sung by
a Canuck.
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We usually put on the Vienna Boy's Choir, or some german Christmas music from the 1950's and 1960's. It's a 32 year family tradition that we gather 'round the tree and sing "Stille Nacht". In German. OK, my wife and I sing it in German, the kids mumble along. We adopted almost all of my wife's family's Christmas traditions. Except I don't hit the Slivovits as hard as her dad usually did. Or complain about the food.
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Album...gotta go classic: Christmas With The Conniffs
Individual Song Category
White Christmas - Bing Crosby
Bruce Springsteen - Santa Claus Is Comin To Town
Red Peters - Holy Shit It's Christmas
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Holy smokes, 43 posts so far and still going strong! I'm going to spend tonight listening to the music listed here. I already bought one album based on these recommendations.
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Haven't listened to their album, but favorite live Christmas show is Celtic Woman.
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Late to the party but I love harmony (someone else mentioned Strait No Chaser, but I also love the Roches "We Three Kings" and Aliqua "All I Want"
Kate
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Can’t recommend this as classic Christmas music, and I enjoy a nostalgic trek by listening to at least one lot-time radio program. Here you can find “The Great Gildersleeve” episodes.
“Leroooooyyyy!”
http://www.greatgildersleeve.com/christmas.html