My 400 Favorite Modern Christmas Songs, The Top 20!

Many of you are thinking that we are FINALLY diving into this guy’s Top 20 modern Christmas songs. It’s about time, since you made us suffer through 380 other songs by artists we still have no idea who they are. What can I say? I truly do dig all these different versions of the same song, song or hymn. Plus, I left off many other fun songs by artists, both known and obscure.

There are many great Christmas songs by the likes of Sting, Pet Shop Boys and Los Lobos, while my personal favorite seasonal novelty song was left off the list, the immortal “I Farted on Santa’s Lap” by the appropriately named The Little Stinkers. I undersold the holiday work of Elvis Presley, Johnny Cash and Dolly Parton, while I acknowledge that Mariah Carey is the Queen of Christmas music we all better not sleep on Kelly Clarkson who has recorded two terrific Christmas albums in the past decade or so.

Perhaps, the thing I wanted to point out most of all is that you, the avid music listener, do NOT have to listen to the same small playlist, albums or radio version of popular Christmas music. There are many absolutely wonderfully fun and moving recent pop songs of holiday music that are totally being overlooked by radio programmers and algorithms. And, I want to bring these songs into the daylight, so some of you might seek them out and include them in your current or future holiday playlists.

Now, it’s time to see just what holiday standards made my personal Top 20.

20. John Mellencamp – “I Saw Mommy Kissing Santa Claus” (2007). When he recorded this songs, Mellencamp was at his career peak. He and his band had perfected his Hoosier mix of Appalachian country/folk instrument and Rolling Stones crunch. John and his band find the missing rock and roll aspect of this holiday classic.

19. Dolly Parton – “Hard Candy Christmas” (1984). This song only seems to improve with age. No one, absolutely no one, writes broken-hearted songs like Dolly does, and she couples the sentiment with Christmas in this should-be-a-classic.

18. The Band – “Christmas Must Be Tonight” (1975). Can we all agree that Robbie Robertson knows his way around song narratives? This long-overlooked Christmas song needs to become a modern classic. Robertson just nails the Christmas story perfectly in three minutes that must ministers can’t make in a half-hour sermon.

17. Taylor Swift – “Christmas Tree Farm (Old Timey Version)” (2021). This song should have been all over radio when the original version was released two years ago. So, Taylor, whose been on a major roll re-recording back catalog, eschews the folky original to give this brilliant song a more traditional, Sixties-like production, turning the song into a timeless classic.

16. Band Aid – “Do They Know It’s Christmas?” (1984). This song is ground zero for the MTV generation’s obsession with, first, holiday songs, and, two, charity singles. By now, we all know how clunky and awkward the lyrics are, but everyone’s hearts were in the right place. So, emotion won out in the end. Let me give a shout out to one of my all-time faves, Paul Weller, for his contribution (Put The Jam in the Rock Hall!).

15. Bobby Helms – “Jingle Bell Rock” (1957). Helms was a budding country artist in the Fifties when he wrote and recorded this modern yuletide classic. Like Mellencamp and me, Helms is a Hoosier, all the while maintaining a modest lifestyle in southern Indiana. Yet, his Christmas classic is everywhere each December, which continues to keep his estate financially secure.

14. Brenda Lee – “Rockin’ Around the Christmas Tree” (1958). Here is yet another classic from the early days of rock and roll. The next time you listen to Brenda Lee’s Christmas tune, think about her being in her early teens when she recorded this song. Some people are simply blessed with a gift. Brenda was blessed with two: first, her voice and, second, this song.

13. Cheech & Chong – “Santa Claus and His Old Lady” (1971). When I was a kid, Cheech & Chong’s brand of drug-based humor was second only to Richard Pryor. But, their take on Santa’s story is brilliantly hilarious. Unfortunately, this might have become something of a relic in the post-“Just Say No” days. But, what can you say when you discover that Santa’s reindeer get their ability to fly from “magic dust.” “A little for the reindeer, a little for Santa, a little more for Santa, a little more for Santa…” The Seventies truly were a more innocent and much different time.

12. The Regrettes – “Marshmallow World” (2016). Just as Darlene Love’s version jumped from the mono car radio due to Phil Spector’s production in 1963, The Regrettes neo-New Wave take on this classic jumps out from my smart speaker. This version is so fun that it was used in a Target commercial a few years ago. See? I am NOT totally stuck in the 70s/80s/90s.

11. Dan Fogelberg – “Same Old Lang Syne” (1980). Once again, this song only mentions in the opening line that Fogelberg ran into a past flame in a grocery store on a Christmas Eve. So, technically, it’s probably not really a Christmas song. But, the holiday season is about reunions, so why not a couple of high school sweethearts getting reacquainted. It is a very touching song and just might be Dan’s best moment. By the way, did you know this is a true story? A year ago, I read an article about the girl in the song. Her story is pretty cool. Check out the story: https://www.pjstar.com/story/entertainment/music/2020/12/14/dan-fogelberg-same-old-lang-syne/6494479002/

10. Elton John – “Step into Christmas” (1973). Elton was the MAN when he recorded this song. Now, it’s become something of a modern Christmas classic. I will always associate this song with American Bandstand during their Christmas-themed shows during the 70s.

9. Stevie Wonder – “Someday at Christmas” (1967). This anti-war yuletide song has long been one of my all-time favorites as it combined socially-aware lyrics with Christmas themes. And Stevie was just beginning to discover his adult songwriter’s voice on this song.

8. Billy Squier – “Christmas Is the Time to Say ‘I Love You'” (1981). Squier was red-hot in 1981 and 1982. So, it was no wonder that he was invited to MTV’s second on-air Christmas bash. This classic was recorded live in front of a bunch of drunk members of MTV’s staff.

7. Bing Crosby & David Bowie – “Little Drummer Boy/Peace on Earth” (1977, released 1982). I remember hearing that Bing, my maternal grandfather’s favorite singer who had passed away just two years earlier, was singing a duet with one of my favorite artists on his Christmas special, I knew I had to watch. What I did not know was that Bowie didn’t want to sing “Little Drummer Boy,” so he and Bing worked up the arrangement of this medley an hour before recording it. This song may be the most sentimental holiday song for me because of my grandpa.

6. Harry Simeone Chorale – “Little Drummer Boy” (1958, 1965). As a young boy, my parents would try to send me to bed early on Christmas Eve. So, for the next couple of hours, I would listen to my GE AM-only bedroom radio while reading books. It seemed as though the local radio station’s last song every Christmas Eve night around their midnight sign-off would be this song. At first, I hated to hear it played, but as I got older I began to appreciate the vocal arrangements and this acapella hit began to grow on me. Now, it reminds me of those cold Christmas Eve nights as child anticipating Santa’s arrival.

5. Daryl Hall & John Oates – “Jingle Bell Rock (Daryl’s Version)” (1980). The duo was just beginning to exert their 80s dominance when they recorded two versions of this classic, with the versions sung by each man. When the songs were released, one version was pressed on red vinyl while the other one on green vinyl. Of course, since I am a HUGE fan of these guys, I own both. But, it is Daryl’s version that radio has played over the years. But, to my ears, the “rock ‘n’ soul” duo out-did the original, especially when coupled with its cheesy parody video. Classics are both.

4. John & Yoko with The Plastic Ono Band – “Happy Xmas (War Is Over)” (1971). It’s rare when a song works on multiple levels, but when someone can have a hit pop song that is a great protest song in addition to becoming a Christmas classic, you have a major piece of art. Lennon takes Wonder’s sentiments and raises the bar. This song is eternal.

3. Mariah Carey – “All I Want for Christmas Is You” (1994). Give Mariah credit. She wrote a monster song, not just a monster Christmas song. This song was a holiday classic from the moment is was released. It is a perfect song, not just a perfect Christmas song. It contains musical nods to Motown and the 80s all the while feeling totally fresh, even 30 years later. Plus, the song has shot to number one on Billboard‘s Hot 100 each of the past three years. No other song has done that.

2. The Ronettes – “Sleigh Ride” (1963). This song is from arguably the greatest Christmas album ever recorded (A Christmas Gift to You from Phil Spector). This song is just terrific, from the horse sound effects to the driving rhythm of the Wrecking Crew’s playing. Now, this album and song are considered to be classics. But, it did get off to an auspicious start as the album was released on the day that President Kennedy was assassinated. At least it has found an audience now.

1. Bruce Springsteen – “Santa Claus Is Coming to Town” (1975, released 1985). The Boss took the arrangement of The Crystals’ version from the Phil Spector album and distilled it through his Born to Run-era romantic period to marry Christmas to modern rock music. This is Christmas music at its very best while Bruce takes the song to a whole other level in concert. This one has brought me much joy over the past 45 years, that I have passed on to my boys and, now, my grandchildren who must hear it when they enter our home.

And, there you have it. I know, I ranked “White Christmas” and “Do You Hear What I Hear?” lower. Well, who do I knock out of my Top 20? See? It’ much harder than it looks.

Author: ifmyalbumscouldtalk

I am just a long-time music fan who used to be a high school science teacher and a varsity coach of several high school athletic teams. Before that, I worked as a medical technologist at three hospitals in their labs, mainly as a microbiologist. I am retired/disabled (Failed Back Surgery Syndrome), and this is my attempt to remain a human. Additionally, I am a serious vinyl aficionado, with a CD addiction and a love of reading about rock history. Finally, I am a fan of Prince, Cheap Trick, Tom Petty, R.E.M., Hall & Oates, Springsteen, Paul Weller & his bands and Power Pop music.

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