Music has always been a huge part of my life. It surprises me that— in the 23 years I have occupied this weekly space— I have never written about music. I am such an ardent admirer of all genres of music I could have been writing a bi-weekly column for the past 23 years and would still have a mountain of songs, artists, and albums I haven’t covered yet.

I love Christmas and I love Christmas music. I break out the Christmas files immediately after Thanksgiving. It reminds me of all the fondest memories in my childhood. My son doesn’t like Christmas music. He says, “There are only two dozen songs covered by three dozen people.” Scrooge.

My response to that comment is, “But those songs must be good, or so many different people wouldn’t be singing them.” One thing you won’t see on this list is any song on the Chipmunks Christmas album. I loved it as a kid, and almost drove my grandfather to the mental hospital playing it. I’m not a fan today. I have become my grandfather (who loved a few songs on this list).

The following are my Top 20 Christmas Songs:

Honorable Mention: “Feliz Navidad,” Jose Feliciano— There’s something that is so festive about this Christmas song. I have been a Feliciano fan since he covered the Doors’ “Light My Fire.”

20.) “Wonderful Christmastime,” Paul McCartney— People have strong feelings about this song. Most of them are negative. I’ll admit it’s a little heavy on Linda’s synthesizer. But I was a radio station disc jockey in my pre-restaurant days, and I had to pull 12-hour shifts during the holidays because everyone wanted time off and I was a 15-year-old willing to work anytime if I could be on the air playing music. This was in heavy holiday rotation in those days. Plus, it’s Paul McCartney!

19.) “Santa Claus Is Coming to Town,” Bruce Springsteen— Such a great version of this song. Again, from the 1970s. It follows an entirely different beat structure than the original and is made better by Clarence Clemons adding the “ho, ho, hos.” I like the change in meter from the version I grew up with.

18.) “The Christmas Waltz,” Frank Sinatra— I could fill this entire list with Frank Sinatra Christmas carols. He nailed every one he ever sang.

17.) “Christmas in New Orleans,” Louis Armstrong— When I was a kid, my mother would take my brother and me to New Orleans to Maison Blanche to see Santa, shop for presents, and eat lunch at Galatoire’s. Two words: Mr. Bingle. If you know, you know. Satchmo owns this one.

16.) “Mary’s Little Boy Child,” Harry Connick Jr.— Another New Orleanian nailing a Christmas carol. The modern spiritual is given a New Orleans backbeat and is allowed a lot of space to get funky. I typically don’t like “funky” in my Christmas music, but it sure works here.

15.) “All I Want for Christmas Is You,” Michael Bublé— He owns this song more than Mariah Carey, thankfully.

14.) “Holly Jolly Christmas,” Burl Ives— I was a huge fan of the 1964 stop-motion version of the Rudolph the Red Nose Reindeer television special. It was an event every year in my childhood. 

13.) “The Christmas Song,” Nat King Cole— I am not a fan of roasted chestnuts, but I am a huge fan of the silky cool voice of Nat King Cole. He was an excellent— and underrated— pianist. Check out his instrumental album in the off season. 

12.) “Merry Christmas Darling,” The Carpenters— Again, this makes me think of late-night shifts alone in a radio station control room during the holidays in the 1970s. My wife is not a fan, so I only listen to it when she’s not around.

11.) “Merry Christmas from the Family,” Robert Earle Keane— Such a hilarious song. You can have “Grandma Got Run Over by A Reindeer.” Give me Robert Earle Keane every day.

10.) “That Spirit of Christmas,” Ray Charles— One of America’s most iconic voices signing Christmas songs? Sign me up. Plus, this song is in the only serious and touching scene in “National Lampoon’s Christmas Vacation.” The rest is hysterical.

9.) “O Come All Ye Faithful,” George Jones— Ol’ Possum does Christmas, and he sings this song so well, no one should ever attempt to sing it again.

8.) “The First Noel,” Jerry Vale— This is my favorite Christmas carol. Period. Close the hymnal. I’d rather hear it sung by a men’s chorus, but Vale does it justice with sufficient backing vocals and nice orchestration. Some songs don’t need to be jazzed up and need to be sung straight. This is one of them.

7.) “Winter Wonderland,” The Eurythmics— This song works well jazzed up. Annie Lennox and Dave Stewart do a great updated version. It has a very 1980s vibe, but it holds up in my opinion.

6.) “Sleigh Ride,” Boston Pops Orchestra— When our kids were young, we would take them to Disney World the week after Thanksgiving. It’s the best time to go because it’s one of the slowest weeks of the year for them, but it’s all “done up” for Christmas. This version plays often throughout the parks. It makes me think of my kids at Christmas. Is there a better thought, ever?

5.) “White Christmas,” Bing Crosby— It’s the best-selling song of all-time for a reason. I never cared for the movie, but no one sings this one like Bing.

4.) “Silver Bells,” Dean Martin— Like Sinatra, I could fill this list with 20 Dean Martin Christmas songs. He’s the king of cool, and around my house he’s the king of Christmas.

3.) “Rudolph the Red Nosed Reindeer,” Billy May— This came on a Christmas Cocktail/Lounge compilation CD I bought years ago. My kids love this song. Therefore, I love this song. Billy May wrote arrangements for Sinatra, Nat King Cole, and others. This is a fun, upbeat, mambo version of the Gene Autrey classic, and better than the original, by a mile.

2.) “Mistletoe and Holly,” Frank Sinatra— Again Sinatra made any song better. He was such a great crooner of Christmas songs, I have a file in my playlist library that is nothing but Dean Martin and Sinatra Christmas songs. He wasn’t a songwriter, but he wrote this one.

1.)“Do You Hear What I Hear,” Whitney Houston— Her legend grew when she sang the national anthem at the 1991 Superbowl. This version should be given equal respect. Houston takes this one to church. The entire arrangement is first rate, from the gospel chorus to Houston’s amazing voice in her prime. This is an amazing vocal performance. I would have loved to have seen her perform this live with an orchestra and choir.

There is a link to this playlist below.

Onward