I had a friend who posted her top 10 classic Christmas songs, and I thought, "Hey! That's cool! I should do that, too!" So, just remember Kelly - copying is a form of flattery. ;-)
The following lists are not in any particular order, but rather as I come across them.
Riki's 5 Favorite "Traditional" Christmas Songs
Typical Christmas carols, with all the churchy goodness.
1) "O Holy Night" - There are a number of artists who have covered this song. I remember first falling in love with it when listening to Hanson's "Snowed In" Christmas CD when I was 13. I suggest the Trans-Siberian Orchestra's version of this song, but any will do.
2) "The Holly & The Ivy" - No idea what my favorite version of this song is. All I know is that I love it.
3) "Angels We Have Heard On High" - Again, no clue what my favorite version is. I know this is my mom's favorite Christmas song, though. I grew up knowing that, and I think it just slowly became one of my favorites, too.
4) "The Twelve Days of Christmas" - There have been some great versions of this. The only one I can listen to more than once a season, though, is John Denver & The Muppets ("Fiiiiiiive gooooooooold riiiiiings... Ba dum, dum, dum!"). Classic. <3
5) "Silent Night" - It's too classic not to be on my list. Instrumental versions can be just as beautiful as vocal ones, and no matter what, you'd recognize it as a traditional Christmas song.
Riki's 5 Favorite "Popular" Christmas Songs
The songs that everyone adores, but you probably wouldn't sing door-to-door.
1) "Sleigh Ride" - Doesn't matter which version; it always gets me bouncing along. Though, I do really enjoy the Boston Pops version (if for no other reason, than the whip noise they make).
2) "White Christmas" - My favorite version has to be The Drifters (a la "Home Alone"). What's more fun than singing, "I-yi-yi-yi'm dreaming of a white Christmas..."? Few things, my friends. Few things.
3) "Have Yourself A Merry Little Christmas" - I adore Judy Garland singing this song, but my true favorite comes from the John Denver & The Muppets Christmas special. John and Rowlf do this as a duet, and it melts my heart every time I hear it.
4) "Santa Baby" - Eartha Kitt's version is the only one worth listening to (sorry, Madonna).
5) "Feliz Navidad" - I just want to rock out to this every time I hear it. Kudos to you, Jose Feliciano!
Riki's 5 Other Favorite Christmas Songs
These are the songs that you probably have heard, but you might not even know they exist. Some of them could be put into the category above, but they get a special place because I love them so much.
1) "The Chipmunk's Christmas Song (Christmas Don't Be Late)" - Because every kid still wants a hoooooooola hooooooooop.
2) "I Want A Hippopotamus For Christmas" - Gayla Peevey had the original of this song. I believe it has since been re-done, but I still go for Gayla's version. :-)
3) "364 Days To Go" - One of my favorite Brad Paisley songs, this is a sweet song about waiting for Christmas.
4) "Song For A Winter's Night" - Sarah McLachlan does such a beautiful job with this song.5) "The Christmas Song" - Not the song you'd expect by the title, this is Weezer singing a fairly sad song that I can't help but love.
Now, you have to understand that I love probably 99% of all Christmas music, so this is just a sampling of the songs I truly enjoy each winter. There are TONS more songs that I could've included, but there's only so much time in the day, my dears.
Now go get your carol on!