My Favorite Christmas Songs

Recently, I posted my favorite fall/winter seasonal songs as I made the argument for separating seasonal and Christmas songs. For numerous reasons, Baby It’s Cold Outside, which is not even a Christmas song, will not be on this list. We can discuss it all you like, but I just don’t think it’s appropriate anymore. As I mentioned in the previous entry, I am curious to know in what year these songs were written, recorded, and released. Many of them are just flat-out timeless.

I, again, enjoy the original definitive version of these songs, and I really don’t care for any “new” Christmas music. I make one exception. Since we went early with the seasonal songs this year, we’ll post this now so you have plenty of time to get in the Christmas spirit.

Rockin’ Around the Christmas Tree

Brenda Lee recorded this song when she was all of 13 years old and it was released in 1958. I enjoy the rockabilly sound. One of the more popular Christmas tunes, it hit the Billboard charts more than once.

Silver Bells

When I was a kid, I loved the Bob Hope Christmas specials, mainly to see the Playboy (later Associated Press) college football all-star team. I eventually learned about Hope and his efforts to entertain the troops. I also learned to appreciate Hope’s humor and his legacy. On every Christmas special, Hope would perform a duet of Silver Bells. The song was written by Jay Livingston and Ray Evans and released in 1950.

It’s the Most Wonderful Time of the Year

It may as well be a Christmas anthem. Upbeat and festive, this song, made famous by numerous singers, heralds the arrival of the Christmas season. I couldn’t have this list without something from Mr. Christmas himself, Andy Williams. Williams made Christmas his own cottage industry in Branson, Missouri. He too was known for television Christmas specials.

Mistletoe

This is my one exception when it comes to newer Christmas music. Colbie Caillat co-wrote this with Mikal Blue and Stacy Blue in 2007. I love this tune. I am a fan of Caillat’s music and this song has a story and a touch of melancholy to it that I really like.

It’s Beginning to Look a Lot Like Christmas

Another Christmas anthem that rings in the season, this song was written in 1951 by Meredith Wilson. Numerous artists including Bing Crosby, Perry Como, Johnny Mathis, and more recently, Michael Bublé, have recorded versions of this classic. I’ll leave you with Bublé’s version. His Christmas album from a few years ago is a real treat.

Santa Claus and His Old Lady

When I was a disc jockey with Armed Forces Radio, we would start the season with one Christmas song an hour and build up the frequency as December 25 approached. I discovered Cheech and Chong’s Santa Claus and His Old Lady, played it for the first time and fell out of my chair. More spoken word performance than a song, it’s hilarious.

Christmas in Hollis

Okay, I lied. There’s another newer, original song I like. I grew up on hip hop music and one of the first groups of which I became a fan was Run DMC. And yes, they did a Christmas song. It has an infectious hook and a great beat. It’s different and a sign of the times, 1987 to be exact, the year I graduated high school.

Little Drummer Boy

I am not a big fan of this song, but Bing Crosby and David Bowie combined for an unexpected version of the song on Crosby’s last Christmas special, and I just had to include it. Katherine Kennicott Davis wrote the tune in 1940 and it was first recorded by the Trapp Family Singers in 1951.

Carol of the Bells

The song that everyone sets their computerized outdoor light display to, and the only song of its kind that I like.  Written by Mykola Leontovych and Peter J. Wilhousky in 1914, I prefer Trans Siberian Orchestra’s version.

The Christmas Song

Written in 1945 by Robert Wells and Mel Tormé (The Velvet Fog), this one has become an endearing Christmas classic. Covered by countless artists, this song evokes images of warm Christmas wishes. I prefer Nat King Cole’s version.

I’ll Be Home for Christmas

I spent 10 years in the United States Navy and I spent many a Christmas away from home. I also traveled quite a bit for the profession I spent 20 years in, and missed a few Christmases working. This song hits home for numerous reasons. Written by Kim Gannon and Walter Kent in 1943, it was recorded by Bing Crosby the same year. I like Frank Sinatra’s version.

A Holly Jolly Christmas

I just had to have something from Burl Ives. Written by Johnny Marks in 1962 and included as part of Rudolph the Red-Nosed Reindeer, Ives recorded the definitive version. This is one of the more popular songs for current artists to cover.

White Christmas

I’ll end this list with what has become my favorite Christmas song. I don’t like musicals, and can’t stand them, but a few years ago I finally gave White Christmas a shot and I was hooked. The song, written by Irving Berlin, debuts in 1942’s Holiday Inn, but it became a staple when Bing Crosby’s hit musical of the same name took off in 1954. This is one of the most popular songs of all time. Here is Bing Crosby with Frank Sinatra.

My Favorite Seasonal Songs

Since everyone is so keen on starting Christmas so soon, and re-gifting is such a thing these days, I thought I would recycle a piece I wrote a couple of years ago. I will not succumb to Christmas Creep, but the temperature has dropped, the days are getting longer, and we’re on the backside of Halloween, so I guess we can start with SEASONAL songs.

Something struck me as odd a couple of years ago. I do love Christmas music and I prefer the traditional or definitive versions … and in many cases that means the original. I also started to wonder when some of these songs were written because of the myriad musical styles represented. I was listening to Holiday Traditions on SiriusXM in December 2019 and I realized that many songs we identify as “Christmas” songs are actually seasonal and have nothing to do with Christmas. That doesn’t mean I like them any less, they just deserve their own list.  So, I decided to split them up.

Here are my favorite fall/winter seasonal songs.

Winter Wonderland

Winter Wonderland, written in 1934 by Felix Bernard and lyricist Richard Bernhard Smith, has been recorded by countless artists over the years. It’s a fun, upbeat song that we all know and can sing by heart. I prefer Johnny Mathis performing this one.

My Favorite Things

I am not sure how this song, most famously performed by Tony Bennett, got to be associated with Christmas. Perhaps the visuals and references place it around Christmastime. It originated in 1961 with Julie Andrews on The Garry Moore Show’s Christmas special. Andrews also performed it in The Sound of Music, both on Broadway and in the film. Written by Rodgers and Hammerstein, this has become a seasonal jazz favorite.

Happy Holiday

This is another song that is commonly associated with Christmas although it was written for a movie that encompasses all holidays. Written by Irving Berlin and performed by Bing Crosby and Martha Mears in the 1942 film Holiday Inn (and yes, the hotel chain was named after the film), this version references the holiday-themed hotel Crosby’s character opens.

Sleigh Ride

This is another song that I really don’t know why it became associated with Christmas. It is my favorite fall/winter seasonal song and Johnny Mathis’ version is the one I prefer. This great tune has been recorded by countless artists as well. Written by Leroy Anderson in 1948, Sleigh Ride is considered an orchestra standard and it was first recorded by Arthur Fiedler and the Boston Pops in 1949. Mitchell Parish added the lyrics in 1950. I usually try to listen to this one first to kick off my holiday music listening season.

Jingle Bells

There’s a theme here. I have no earthly idea how this song became associated with Christmas either. It just might be the oldest seasonal song that surfaces during the holidays. Written by James Lord Pierpont in 1857, zipping along in a one-horse open sleigh might have been the preferred method of transportation during the winter months when the song was composed, although it was supposed to be a Thanksgiving song. Numerous variations of the lyrics have been recorded over the years, including what would be considered politically incorrect (by today’s standards) references and accents regarding winter in Mexico most notably recorded by the Glenn Miller orchestra. Let’s go with Ol’ Blue Eyes.

Marshmallow World

This song was practically tossed on the scrap head of forgotten seasonal songs until SiriusXM resurrected it, and when it was recently used in a commercial. Perhaps the best version was recorded by Dean Martin. Written in 1949 by Carl Sigman and Peter DeRose, the song celebrates simply playing in the snow. 

Let it Snow

Written by Sammy Cahn and Jule Styne in 1945, this song doesn’t exactly celebrate snow, rather extols the virtues of staying in and getting cozy. Since this list is pretty male heavy, let’s go with the great Doris Day for this one.