River – Sarah Mclachlan
I’d only vaguely heard this song before I bought Sarah’s Christmas album. It’s melancholy but somehow not in a bad way. I don’t even know how that works. Her version of “O Little town of Bethlehem” is also worth a listen or twenty.
Gothic Christmas – Within Temptation
This song is cheesy and ridiculous, and I love every moment of it. Let’s talk about evil Santa and Rudolph (not Krampus). Let’s make everything sparkly and green
Leroy The Redneck Reindeer –Â Joe DiffieÂ
Speaking of cheesy, there’s this one that’s about 20 years old. It’s got that Christmassy feel but it’s totally got that dated 90s country sound, too. And it’s going on my iPod as I type!
Deck the Halls – SheDaisy
Slightly less redneck is SheDaisy’s version of “Deck the Halls,” which might be the only version I actually like. It sounds so grown up, and it’s crazy to think I first heard this when I was in high school!
Winter Dreams – Kelly Clarkson
Kelly Clarkson’s Christmas album is one of the better modern Christmas albums in my opinion. There are some classic covers, but the new songs manage to capture the feel of Christmas and the jazzy tempos match Kelly’s powerful voice so well. “Winter Dreams” could be my favorite Christmas song of all time, but “Underneath the Tree,” and “4 Carats” are excellent, too.
A Mad Russian’s Christmas – TSO
It’s all really hard for me to pick a single song by TSO that I like. I know that most people only like Christmas Eve in Sarajevo, and it’s good, but they’ve  got multiple Christmas albums! “Wizards in Winter” is a song that I keep on my iPod all year long, so I think that shows you how much I like it. But “A Mad Russian’s Christmas” ugh. It’s everything, guys!
Sufjan Stevens – Christmas In The Room
If you want coffee shop indie music, then this last track is the one for you. It’s not my favorite on this list, but it’s definitely enjoyable and festive/