Christmas Playlist

Hey everyone! It’s Ryan with another monthly installment of the Playlist Challenge. This should be a fun one so hopefully you guys want to participate on this one. As always, here are the rules. I will post a 20-song playlist on a certain topic complete with explanations for each song. I challenge each of you, Brent included, to do the same. Once you see this, shoot us an email at and put “Playlist Challenge December” in the subject line.



The time is upon us once again! It’s my favorite holiday, and we’re going to explore the best music of the season. This is a tough playlist. Christmas music typically stays the same for a long time, but it would surprise you just how many hidden gems of the holidays there are out there. I’m adding one additional rule to this playlist. You can only have one version of any given holiday song on your list. I better not see 20 versions of Silent Night here. Anyways, without further ado…


The Playlist:


1. God Rest Ye Merry Gentlemen/We Three Kings- Barenaked Ladies and Sarah McLachlan

You’ve already heard me rave about this song. It’s without a doubt one of my very favorites of the season. The only bad part about this upbeat, jazzy number is that it knocks two potential songs off my list. Oh well, it’s worth it.


2. Christmas At Ground Zero- Weird Al Yankovic

If you don’t like this song, then I hope you get mauled by a mutant. This blend of dark humor, Cold War paranoia and festive spirit is one of the best non-parody works Weird Al has ever done. It’s a refreshing change of pace to hear a dark Christmas song which will explain a couple of my choices on this list.


3. The Little Drummer Boy- Bob Seger and the Silver Bullet Band

This song is really easy to fuck up. Too often artists will over-sing the “ruppa-pum-pums” in an attempt to show off their soulfulness and it comes off as stupid. Soulfulness has always been a strong suit of one Bob Seger though, so naturally his version would strike the right balance. Seger actually took his inspiration from Mo-Town Christmas albums here and it shows in the use of back-up singers on the track. All in all, Seger succeeds where many others fail.


4. Christmas Wrapping- The Waitresses

There aren’t many Christmas songs that deal with the idea of Christmas as the end of the year, much less the end of a stressful year. That narrative thread carries through this song and it creates exactly the kind of story you’d expect from this new wave ensemble. It’s got a good groove to it too.


5. Christmas Card From a Hooker in Minneapolis- Tom Waits

This bourbon-swilling ballad reads a Christmas card sent to a man named Charlie from a former lover detailing her life since he left. There isn’t a whole lot of yuletide festivity in this song, but it does deal with feelings of sadness that a lot of people feel over the holidays. It’s a very Waits song. In fact, it just may be the perfect Waits song. It’s an interesting addition to any Christmas playlist though…unless your parents are around.


6. Step into Christmas- Elton John

It’s an upbeat party song about relaxing at the end of the year. It’s also Elton John, so if that doesn’t sell you on it then I can’t help you. This has been a holiday favorite since its release in 1973 and it still rocks today.


7. Thank God It’s Christmas- Queen

Freddie Mercury singing a Christmas song that isn’t “Do They Know It’s Christmas?” In immediately.


8. O Come, O Come Emanuel- Rob Halford

Sometimes it’s hard to be both a metal fan and a Christian…but this song makes it easier. Rob Halford is amazing as always on this song and this entire album is quite fantastic. If you find yourself bored with the typical Christmas offerings and want something festive to headbang to, Halford has you covered.


9. This Christmas Day- Trans-Siberian Orchestra

It’s hard not to go with TSO’s signature tune “Christmas Eve/Sarajevo” but this track is just too powerful to ignore. Its placement in their live show is a culmination of emotion and symphonic wizardry and even outside of that context it hits like an atom bomb of good feelings.


10. Loving Time of the Year- Travis Tritt

This won’t be the last country track. Forewarned is forearmed. That being said, Travis Tritt gives us a great song about the positive feelings associated with Christmas. One of the reasons why I love this time of year so much is that all of my family comes together to celebrate it. I love the feeling of closeness that Christmas brings and much like in the song, I wish I could have this feeling every day.


11. There’s a New Kid in Town- Kathy Mattea

Kathy Mattea’s “Good News” is my favorite Christmas record of all time. It’s a beautifully performed album of very worshipful material. For those of you who are religiously inclined, this album is a must-listen. I used to favor the George Strait version of this song, but over the years this version has eclipsed it for me.


12. Do You Hear What I Hear- Any Version

This is one of the most undeniably beautiful Christmas songs of all time. Literally any version will do. I like the Celtic folk flavor of this version, but you can replace it with Whitney Houston, Carrie Underwood, Bing Crosby, or anyone.


13. White Christmas- Bing Crosby

Bing has to make this list. No doubt about it. So let’s place him on the list with the song he made famous in two different Irving Berlin musicals. Of the two, I prefer “White Christmas” personally, but that’s a different subject matter altogether.


14. Auld Lang Syne- Any Traditional Arrangement

Speaking of needing a Celtic flavor, let’s throw New Years standard, Auld Lang Syne on the list. Dougie MacLean has a good arrangement, but there are several acceptable versions out there.


15. Jingle Bells- Jimmy Buffet

This song can be absolutely infuriating this time of year, but I find Jimmy Buffet’s reggae version of the worn-out cliche endlessly endearing. Is it offensive? Of course not! If you’re offended by Jimmy Buffet then you need more adversity in your life.


16. The 12 Days of Christmas- Straight no Chaser

This is one of those rare situations where someone combined two things I hate and made something I love. Make no mistake, the 12 Days of Christmas is dogshit and a capella is a waste of time…but these guys seamlessly combine talent and humor to create a very fun listen. the ending is a great payoff too.


17. You’re a Mean One, Mr. Grinch- Thurl Ravenscroft

Can’t beat the classics. Especially when the classics consist of Tony the Tiger singing a song written by Dr. Seuss himself.


18. A Miser Brothers’ Christmas- The Miser Brothers

Fuck you, I love these songs! I watch this movie ever year (sometimes a few times) and I sing these songs all the time. You’re lucky I didn’t split this entry in two.


19. Christmas All Over Again- Tom Petty & The Heartbreakers

It’s a classic. You all probably knew it was coming. Yet another showcase of how talented Tom Petty was.


20. Father Christmas- The Kinks

A very sharp and even depressing Christmas song about a group of kids mugging Santa Claus. Christmas goes punk and I love it.