I thought there’d be some sort of thread for this already, but since there isn’t (at least not an active one), I’m going to count down mine this week, intending to finish up on Christmas Day. Feel free to add your own, or tell me how wrong I am. 
First up, Perry Como’s “It’s Beginning to Look a Lot Like Christmas” at #25. Bing Crosby released a fine version around the same time, and Michael Buble did a nice recent update as well; but I just love the weird little laugh Como lets out from 1:21-1:25, so that sealed the deal.
My #24 is from Frank Sinatra, whose 100th birthday was celebrated last week. Here he croons “Have Yourself A Merry Little Christmas”. Ol’ Blue Eyes famously asked to have the “muddle through somehow” lyrics changed to make them less gloomy, which is how we got the alternate version “hang a shining star up on the highest bough”.
My #23 song is Brenda Lee’s “Rockin’ Around the Christmas Tree”, which managed to seem to me as a kid, even decades after it was released, at least mildly transgressive for its genre. It’s now nearly six decades old, recorded when Lee was only 13 years old; but it still has an edgy sound IMO. Those swingin’ sax riffs are hot!
Also “rockin’” the holiday season a year earlier than Lee (in 1957) is “Jingle Bell Rock” from Bobby Helms, coming in at #22 on my countdown. It’s not as saucy as Lee’s song, but still has a nice groove to it that I’ve never tired of. I think the song really hits its stride and earns its spot on my list about halfway through, at the 55 second mark.
The first four holiday songs in my countdown were all recorded in the 1950s (three of them in '57 or '58), so of course this one, #21 and my last for tonight, is from…1981. The Waitresses’ “Christmas Wrapping” may not feature virtuosic crooning, but it’s funny and just plain cool.
Continuing the holiday music countdown.
At #20, we’ve got what is really more of a spoken word performance from Johnny Cash. But it’s such a powerful tale of childhood poverty (the kind of poverty that just doesn’t really exist in this country any more), generosity and goodwill toward neighbors, and family togetherness. And it’s apparently a true story, unless Cash was making it all up, which I doubt.
My #19 is sort of surprising even to me. I’m generally resistant to Burl Ives and his talk-singing. I don’t think any of his other songs are even on my broader list of hundreds of Xmas tunes, because I find them irritating. But there’s something about this one that I just find an essential part of the season.
Cheesy though I know it is, I just had to have an Elvis Presley song on the countdown. It was between this one and “Blue Christmas”, but that one is kind of ruined by the overly loud and poorly sung “woo hoo hoo” background vocals, sadly. So this one it is, at #18.
Also knew I had to have a Vince Guaraldi Charlie Brown song on the list, and this one is my favorite, simple as that. #17
#16: I probably listen to more Bing Crosby at Christmastime than any other single artist. I couldn’t narrow my Bing selections down to just one, so I chose one sort of serious, classic “carol” and one more lighthearted, modern tune. This, obviously, is the representative of the former category. Bing really sings his heart out on this one, and the backing choir and orchestra sound great too.
My #15 holiday song is “Santa Baby”, from Eartha Kitt. Great *sounding *song, and still cracks me up every year. So many great lines, but I like the “platinum mine” and “ring” requests the best.
#14 is from the Jackson 5. You’re not going to find many holiday songs with more energy than this one.
#13 is this holiday classic from Andy Williams. It belongs to the category of Xmas songs that is probably my favorite, which could be called “meta-holiday” tunes. That is, songs not about Jesus, not about Santa Claus, but just about the holiday season and the holiday spirit. Not that these make up the majority of my list, necessarily, but if there were more of these that were so well done, they would dominate the list. (I would probably have this in my top 5, but I feel like it has to be played before Christmas Day.)
At #12, I am not necessarily wedded to this rendition of the classic carol “Silent Night”. I just wanted to make sure I got some version of it up on Xmas Eve(ish), and a search of candidates turned this one up, at least as a placeholder for now.
My #11, I had never heard until my wife played me the movie “Love Actually” eight or so years ago. I still prefer this version to Mariah Carey’s.
Top Ten tomorrow…