He'll make this December, the one you'll remember,
The best and the merriest you ever did have
Everybody's waitin' for the man with the bag
Christmas is here again! 
- The Man with the Bag, written by Dudley Brooks; Harold Stanley; Irving Taylor

I've developed a seasonal obsession with Yuletide seasonal music.  I've now got nearly 20 hours of eclectic music for this holiday season, from traditional Christmas to seasonal to even a few Hanukkah songs.  When I edit out duplicates and the ones I really don't like, I still have 240.

I think my obsession started several years ago when I was looking for a version of "Fairytale of New York", by the Pogues, and found it on the compilation Edge of Christmas, along with the Ramones, Kate Bush, Payola$, Queen, and more.  When I finally ripped all my CDs and used iTunes, it got worse. (I don't use iTunes anymore because it'll even encrypt your own CDs if you use it to rip. Evil!)

Every year different songs become favorites. Last year I tried Christmas Gumbo, and instantly fell in love with Art Neville's titular song. It sums up the season very well.  Before that, Amy Grant's "Most Wonderful Time of the Year", and is still high up in my regard. (I'm a sap, deal.)

This year's stand out is the forgotten classic, Kay Starr's "The Man with the Bag" with it's swinging big band and snappy vocals. It's one I inevitably start singing along with (good thing only the cats are around). 

We lived with my grandparents for a while when I was a kid, and my parents are early boomers, so the songs of the 40s and 50s were something I heard a lot of growing up. I admit I do have a fondness for a lot of them.  Bing Crosby's "White Christmas" and Perry Como's "Home for the Holidays" and Nat King Cole's "Christmas Song" were a given in any music being played in December. 

My collection is very eclectic with songs from the last 70 years or so.  I don't have a lot of recent pop songs, and you will never find jingle dogs or anything about matrons trampled by reindeer, even with the assortment of novelty songs. But I do have Thurl Ravenscroft's "You're a Mean One, Mr. Grinch, and Boris Karloff's "Welcome Christmas" which always makes me smile hearing dracula telling a christmas story. 

Thankfully, I don't listen to the radio much so "Christmas Wrapping" isn't spoiled for me. There's some Eagles, and U2, and Pat Benetar. The ultimate christmas song about the actual holy day is Steve Earle's "Nothing But a Child" that really deserved a lot more airplay.

I haven't completed my collection yet; I need to track down Nick At Nite: A Classic Cartoon Christmas, Too which has the Rankin Bass songs, including Heat Miser and Snow Miser. It's discontinued, so I want to find a copy under $20, which is not proving to be easy. And I'm still looking for the ultimate version of O Holy Night.  I may not be Christian but oh, that song makes my skin tingle, but every version I've heard is missing something.

Some suggestions to add to your collection:

Yuletide Songs You May Not Know But Should

All I Want for Christmas Is You by Olivia Olson 

Carol of the Bells by The Bird And The Bee

Christmas Gumbo by Art Neville

Christmas Is Coming by The Payola$

Donde Esta Santa Claus? by Guster )

Fairytale of New York by Kirsty MacColl/The Pogues

Father Christmas by The Kinks 

God Rest Ye Merry Gentlemen by Loreena McKennitt

Got To Get You Under My Tree by Sonny Landreth

I Saw Three Ships by Sting

I'd Like To Hitch A Ride With Santa Claus by The Andrews Sisters

I'm Sending A Letter To Santa Claus by Phyllis Robins 

The Man With the Bag by Kay Starr

Nothing but a Child, by Steve Earle. 

Zat You, Santa Claus? by Louis Armstrong & The Commanders

Yuletide Seaonal Albums that Should be in Your Collection

A Charlie Brown Christmas

A Winter Garden: Five Songs For The Season

Christmas Gumbo

The Edge of Christmas

The Merriest Christmas Album (3 CD set)

Now That's What I Call Christmas, Vol. 3

Wonderland: Cool December

Wonderland: Cool Yule