When I hear the name Judy Garland, two songs come to mind: “Somewhere Over The Rainbow” and “Have Yourself a Merry Little Christmas”. Many versions of both songs have been done but none supersede Judy’s versions. Especially “Have Yourself a Merry Little Christmas”.

This song was written in 1943 by Hugh Martin and Ralph Blane for the 1944 musical film “Meet Me in St. Louis”, which of course stars Judy Garland. There’s a scene in the film where the family is getting ready to move to New York from St. Louis and Esther, Judy’s character, sings the song to her distraught sister Tootie, played by Margaret O’Brien to brighten her spirits.

AFI ranks it at number 76 out of 100 top songs in North American cinema.

I don’t think I’ve ever heard a bad version of this song but Judy’s is special because it’s the only one that has made me cry. Maybe it’s because I recall the scene from the film when I hear it and how sad that seems to me or maybe it’s just the song itself.

What can be said about “White Christmas” that hasn’t already been said? It’s one of the most iconic Christmas songs, with the Bing Crosby version being the best-selling single (in terms of sales of physical media) with estimated sales in excess of 50 million physical copies worldwide.^[3] When the figures for other versions of the song are added to Crosby’s, sales of the song exceed 100 million. (per Wikipedia).

Here I’m going to talk about Crosby’s version because, although countless others have covered the song, in my opinion, his version is the only one that matters.

It’s not clear on where or when Irving Berlin wrote the song but the Jewish immigrant wrote it for the 1942 Bing Crosby film “Holiday Inn”. It went on to win the Academy Award for Best Original Song. The song would also go on to be synonymous with the other Crosby Christmas film classic “White Christmas”.

In 1974 the song was inducted into the Grammy Hall of Fame and per Wikipedia the recording was broadcast on Armed Forces Radio on April 30, 1975, as a secret, pre-arranged signal precipitating the U.S. evacuation from Saigon.

The reason this song is included in my top 25 is because it’s iconic. I find the lyrics very picturesque and sentimental and I enjoy both films the song is featured in. It would be wrong for me to NOT include it on this list. If it weren’t for one other song that hits me harder, this song would be my number one. But it isn’t and I  felt where I put it on my list was a good number for it.

Although this song may not be considered a “traditional” Christmas song, I still feel it IS a Christmas song because it does mention Christmas Eve. I consider it one of my faves because of its bittersweet story. The story just so happens to be true.

Singer/songwriter Dan Fogelberg wrote this and it was released as a single in 1980. It tells the story of a man who runs into his old flame at a grocery store on Christmas Eve and they reminisce about old times over a few beers in her car.

As the story goes, in 1975 Fogelberg had returned home to Peoria, IL to visit family at Christmas. While there he went to a store and ran into his old high school girlfriend Jill Anderson. The two did sit in her car and split a six pack while chatting for two hours.

Imagine Jill’s surprise five years later when she hears “Same Old Lang Syne” on the radio at Christmas. She has said in interviews that she is so glad to have known Dan Fogelberg.

My favorite line from the song is

“She said she saw me in the record stores
And that I must be doing well
I said, “The audience was heavenly
But the traveling was hell”

Which is something I’m sure more than one musician has felt over time.

If anything I feel this song doesn’t get nearly it’s due at Christmas. It really isn’t played as often as it should be.

It just wouldn’t be Christmas without “A Charlie Brown Christmas” and along with it, the opening song “Christmas Time Is Here”.

The song, written by Vince Guaraldi and Lee Mendelson in 1965 was originally written as an instrumental but Mendelson decided it needed lyrics. Add in the children’s choir at St. Paul’s Episcopal Church in San Rafael and you have yourself a standard Christmas hit.

Why I love it: I’m a huge Peanuts fan, especially Snoopy. I have the soundtrack and listen to it even when it isn’t Christmas. Shit, I watch “A Charlie Brown Christmas” even when it isn’t Christmas. And the music makes me happy. It’s jazzy. It’s Christmasy. It’s a great combination.

We all know “River” was written and originally sung by Canadian icon Joni Mitchell in 1971.

But do you know about my favorite version of this song sung by Robert Downey, Jr. in 2000? Yes, Iron Man can sing. And he performs this song so well.

Downey performed the song while a cast member on the hit TV show “Ally McBeal”. His version appears on the “Ally McBeal: A Very Ally Christmas” soundtrack.

So why is this my favorite version? Well, it’s Robert Downey, Jr. A man who has overcome so much in his 59 years and has proven time and time again how talented he is, not just in acting but in singing. This song isn’t the only music Downey has ever recorded. There’s many more. Do yourself a favor and scan Spotify or any music streaming service for his tunes. You won’t be disappointed.