12 Great Songs – My Perfect Holiday Playlist

I love Christmas music.  You heard me! (copyright: Matthew Berry)

This time of year, the sounds of the season bring a bounce to my step and put a smile on my face. As a kid in the stone age of FM Radio, the arrival of the holiday season was doubly exciting because it meant the return of seasonal tunes.

I’m trying to pass on my love of holiday songs on to my girls. It’s a work in progress, so I’m constantly thinking about the right mix of Christmas cuts to play. You can’t go wrong with some holiday standards, but there are some newer songs that capture the mood just right.

My ideal holiday playlist has to include these 12 songs, in no particular order and because it’s a Christmas list, the number 12 is an obvious number.

For various reasons, these songs spark the holiday spirit in me. Got a favorite holiday song? Of course you do. Share it in the comments!

  1. Santa Claus Is Comin’ To Town –  
      It’s not Christmas time until I hear The Boss sing this one.
  2. Holly Jolly Christmas –  
     Stop-motion animated awesomeness, with a bouncy beat from the OG, Burl Ives.
  3. Peace On Earth/Little Drummer Boy – 
    I remember seeing this special with my mom when I was 6(!). The story behind this oddball collaboration is great — so is the fact that I’ve actually spoken to Bowie’s son, Duncan Jones, about being name-dropped in a song that’s now a holiday staple for so many people.
  4. Have Yourself A Merry Little Christmas – 
    – The Judy Garland version is my wife Cindi‘s favorite Christmas song, and in her words, the ONLY rendition of this song worth listening to (she’s a BIG Judy fan)
  5. Step Into Christmas – 
    For some reason, the rock music illuminati of the 1970s apparently had a vote and decided that they all needed to have a Christmas song in their catalog. Elton John’s song is the best of the bunch, and I will fight anyone who suggests otherwise. So Step into Christmas, the admission’s free!
  6. Do You Hear What I Hear – 
    Until recently, I had no idea that one of my favorite holiday tunes was actually created as a call for peace during the Cuban Missile Crisis. It only adds to the poignancy of the song. It’s one of the most covered Christmas songs ever — literally hundreds of artists have recorded versions — but I chose the Martina McBride version, because Martina’s version of any song is always the better version.
  7. A New York Christmas – 
    Do you have any idea how hard it is to create a new holiday standard? Rob Thomas’s new york ditty hits me right in the nostalgia. It came out shortly after we had moved to NYC. Every time I hear it, I picture myself walking through Central Park or down Sixth Avenue.
  8. Mary’s Boy Child – 
     When Cindi and I were dating a few lifetimes ago, this song came on the radio one night as we were driving home from somewhere. I remember her singing along and telling me how much she loved this song. I had never really paid much attention to this Christmas Carol before. But that night, and each time after, I paid attention to the lyrics, and its tender message. Like she has done many other times since, my future wife had shone a light on something new and something beautiful.
  9. Christmas in Hollis – 
    how many suburban white kids learned about the glory of chicken & collard greens from Run D.M.C.?  From the legendary first edition of “A Very Special Christmas” compilation album in 1987.
  10. I Saw 3 Ships – 
    I love, LOVE The Police. I hate, HATE solo Sting. Seriously. Bores me to tears. But his version of this song is perfect. Side Note: The “A Very Special Christmas” compilations have yielded a bonanza of great holiday songs.
  11. Father Christmas – 
    I’m usually a Christmas traditionalist. I love the sappy standards. But The Kinks’ twisted take on holiday songs is irresistible. Side note: I’ll keep this off the kids’ playlist for a few more years.
  12. Do They Know It’s Christmas? – 
    Not only a memorable song, but a great learning tool for young kids. Because there’s no better way to get your child to chill out with their ridiculous holiday wish list than showing them images of starving children in Africa.




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