21 Songs for Your Christmas Week Playlist

piano bear
And the count down to Christmas Day begins!  Happy weekend before Christmas music lovers!  I know most of you will spend it running around doing last minute prep for gifts, holiday soirees, and family visits.  Therefore, I present to you 21 songs to add to your Christmas week playlist to jazz it up a bit, and help keep you sane!  Some of these may be familiar, and others not so much. In no particular or ranking order, let’s get back to more cowbell and get this holiday playlist started!
I should tell you that this is probably one of my favorite holiday songs of all time. It is by far the most realistic depiction of what December means for a working class family, and the commitment and the toll that the holidays can take on the human spirit. This classic belongs on your playlist if for no other reason than to remind you to keep things in perspective.
And of course, let there be Wham! Because when was the last time you actually WATCHED this video? Come on…check it out. Heartbreaking lyrics and a pretty fantastic flashback to the 1980s circa  #1985.  OMG, look at that HAIR! It was like, totally awesome!

For those wishing you were on the beach right about now (or those who escaped and hit the beach for the holidays), and all you Jimmy Buffet genre fans, this one’s for you!

So apparently 1997 was THE year to purchase the yearly released compilation of holiday songs A Very Special Christmas Vol. 3 because every single song on that album is fantastic; therefore in my opinion making this one of the best in this series.  My favorite song on it by far being Blues Travelers Christmastime. The lyrics are especially insightful portraying John Popper’s initial indifference to Christmas, followed by his getting into the holiday spirit, then followed up by his excitement for Christmas the following year. It’s a well done salute to the season that gives a nod to all of the holidays being celebrated by various religions and cultures this time of year and it is truly a beautiful melody.

Blues Traveler- Christmastime (1997)

This won’t be the first time you will see this next band featured in this blog. I will certainly be revisiting them in the near future. Meet Blitzen Trapper, an indie band from the great city of Portland, Oregon. I am loving their sound and this song! It is the most recent addition to my holiday playlist.

Looking for a song that is fun, yet not the traditional Christmas carol, but somehow has the old school sound that is almost Beach Boys style?  I play this next song all the time and I never get tired of it.

XTC (Three Wise Men)- Thanks for Christmas (1983)

Let’s face it. Annie Lennox has an incredible voice. It’s hard to believe that this version has been around since 1987.

The Eurythmics- Winter Wonderland (1987)

And in honor of the fact that for many, the holidays bring all sorts of dysfunctional family dynamics to the surface, here’s a classic from one of my favorite Texas country artists.  Just keepin’ it real ya’ll!

Robert Earl Keen- Merry Christmas from the Family (1994)

It’s been 23 years since Home Alone 2 hit the big screen, and I’m grateful for the fact that it gifted us this holiday hit! Originally penned by Steve Van Zandt featuring members of Bruce Springsteen’s E Street Band as well as members of the Miami Horns, here is Darlene Love singing her heart out!


Because everyone needs a little Billy Corgan in their holiday mix, and because I have absolutely loved this song since its release (in 1997)…it is a must on my holiday playlist.

Smashing Pumpkins- Christmastime (1997)

Now here is a country legend, and classic singing a song whose lyrics are amongst the most clever in the mix of holiday songs. And for those of us who started to catch on, as we started to get a little older, to who Santa Claus really was…this will bring back some fond memories and make you smile.

Santa looked a lot like daddy… or daddy looked a lot like him…

If you’ve never seen this band live, you’re missing out on an incredible musical experience. I featured their latest holiday album Blood Oranges in the Snow in my Thanksgiving weekend blog post: Over the Rhine. Here is an emotionally raw and soul baring song that was released on one of their previous holiday albums. I’ve chosen a link to a live performance because Karin Berquist has an amazing voice and this band sounds even more incredible live. Here’s a song for the more melancholy moments during this holiday week.

If you have been following my blog for a while, then you are already aware that I love this band.  Why not countdown the days with their version of Carol of the Bells? This is by far one of the most unique versions of this carol.

The Bird and The Bee- Carol of the Bells (2007)

Feel like rocking out? Feeling stressed out to the point of being argumentativ? Why not channel that negative energy, belt out this song, and dance it out!

The Ramones- Merry Christmas I Don’t Want to Fight Tonight (1989)

Are you a fan of Zooey Dechanel? (I am!) How about this tune up on a classic?

And just because I can. Because I never leave this song off my holiday playlist since its release….it’s no wonder that it just replaced Mariah Carey’s All I want for Christmas..for the first time ever, as the most played Christmas song of the season! I love The Shins cover of Paul McCartney’s Wonderful Christmastime! (Sorry kiddos, no this is not the original).

I am a big fan of anything written and sung by Joni Mitchell. She just had such an incredible way with words. There are 432 recorded covers of her classic song River. It is the second most covered song in her repertoire. In her honor and as a tribute, here is Sarah McLachlan’s version of River. This is such an incredible piece of music and her version does it justice. It is absolutely beautiful. It brings tears to my eyes.

Sarah McLachlan- River (2006)

No Christmas week playlist would complete without Feliz Navidad!  Here is a more romantic, softer version featuring these two incredible crooners:

Michael Buble & Thalia- Mis Deseos/Feliz Navidad (2011)

Put on the sneakers and get groovin’…let’s get this party started with…

Run- DMC- Christmas in Hollis (1987)

No doubt, I’m a big fan of Gwen Stefani. Remember when she covered The Vandals’ and brought some joy to the world with this rocking ska like masterpiece? The Vandals’ guitarist, Warren Fitzgerald, produced this version for them. In case you missed it, here it is.

No Doubt- Oi to the World (1997)

Last, but far from least, allow me to introduce this incredible version of this timeless classic by a band that I adore. For all of you indie music lovers (and for those in the DC, MD, VA area who remember this incredible local band- they now reside in Portland, Oregon), and all lovers of this traditional song, here is a pretty amazing version of Silent Night. You are going to want to listen to it throughout this coming week and you will never tire of it. Check out these Montgomery County, Maryland natives, and talented human beings that I’ve had the pleasure of meeting and getting to know! Watch Blaine Heinonen and Sarah Wolff sing their hearts out in this living room recording of Silent Night. You can download this great version: HERE!

Pretty Gritty- Silent Night (2011)

And on that note, here’s hoping your Christmas is Merry and Bright! May it be filled with love, joy, and happiness wherever this post may find you.

Merry Christmas music lovers! Thanks for listening!

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