By Dan O'Keefe, OnMilwaukee Intern   Published Dec 24, 2019 at 6:01 PM

Snuggle up with some holiday cheer as OnMilwaukee shares stories of everything merry and bright in the spirit of the season.

Brought to you by Noel Indoor Light Park & Christmas Market and MillerCoors

While the actual day may almost be here, it feels like the Christmas season has been going on forever. That's because of one thing: Christmas music.

Christmas music, along with Hallmark Christmas movies, have become the siren song of the season, creeping closer and closer to Halloween every year. Creeping may be the wrong word; it comes blaring, riding on the voice of Mariah Carey and the wings of all those angels we have heard on high, sweetly singing o'er the plains.

As OnMilwaukee's resident intern who refuses to write anything aside from rankings," I have been tasked with a herculean task: creating a ranking of Christmas songs. Nevertheless, I tackled the assignment with impunity and came up with this list. The criteria for the list was simple: Each song had to be a Christmas song, and only one version of the song could be included on the list. I also grouped some songs into tiers, because hey, why not?

Without further ado, here is the official ranking of the top 25 Christmas songs of all time:

25. "Happy X-Mas (War is Over)" – John Lennon & Yoko Ono

All good Christmas songs should make you feel terrible about yourself. "So this is Christmas, and what have you done?" is such an aggressive way to start a song, especially when followed up with "I hope you had fun." That's just ice cold sarcasm.

24. "Little Saint Nick" – The Beach Boys

This is nearly the same as "Little Deuce Coupe," also by these Beach Boys. "Little Deuce Coupe" is a good song, but it needed a little something extra to make it great. Apparently, the only thing that could bump the song up was ... singing about Santa's sleigh. Santa spends the entire year working on his sleigh, ignoring all his other duties? That's a damning accusation, Mr. Beach Boys.

23. "Christmas Wrapping" – The Waitresses

The "You Can Call Me Al" of Christmas songs: five and a half minutes of rambling, sometimes making sense, staying on two notes throughout, held together by a beat that simply slaps.

22. "I Want a Hippopotamus for Christmas" – Gayla Peevey
21. "All I Want For Christmas Is My Two Front Teeth" – The Chipmunks
20. "I Saw Mommy Kissing Santa Claus" – The Jackson 5

Oh, the joys of children. You want a hippopotamus? Are you up to the responsibility of caring for a living, breathing creature, especially one that can kill you at any moment? Oh, now you just want your two front teeth? What did you do with your last pair? I'm sorry, you saw your mother kissing who now? That's another damning accusation, kid. Don't go writing checks with your mouth that your facts can't cash. 

19. "Frosty the Snowman" – Gene Autry
18. "Rudolph the Red-Nosed Reindeer" – Gene Autry

Gene Autry has FIVE stars on the Hollywood Walk of Fame. He is the only person to have a star for every category, those being film, television, music, radio and live performance. He was one of the most popular performers of his day, and his Singing Cowboy persona had millions of fans nationwide. Now, he is merely known for singing a couple of Christmas songs. That's good! It's good that he's being remembered! He's doing a lot better than some of the other stars of his era. When was the last time you heard someone listening to a Patti Page song?

17. "Sleigh Ride" – Ella Fitzgerald

Ranked due to this scene from "Elf."

16. "What Christmas Means to Me" – Stevie Wonder

I have nothing flippant to say. This is just a banging track.

15. "Last Christmas" – Taylor Swift

A controversial ranking! Taylor Swift over George Michael, the cover version over the original! How dare I? Well, here's the thing: The Wham! version is overwrought and ill-fitting. It's so melodramatic that it doesn't make sense for an adult to sing it to another adult. When it's reframed as a teenage breakup song, it makes perfect sense. That's why the Taylor Swift version made the list: It fits with the era of life so much better.

14. "Christmas in Hollis" – Run DMC

I really wanted to put "Christmas Is" on the list, but it's way less known than Run DMC's other Christmas hit. Although nothing can truly beat a song that starts with "Ho, Ho, Hoin', don't you think on Christmas it be snowin'?" I might have to change my ranking ...

13. "Please Come Home for Christmas" – The Eagles

It's "I'll be Home for Christmas," but sung from the other side – sweet and melancholy. It is funny that Don Henley has decided that, if you can't make it back by Christmas, it would be great if you could make it back by New Year's Eve. He's giving you a six-day extension if you miss the first deadline. I wish I had that kind of time frame!

12. "Carol of the Bells" – Any church choir


11. "God Rest Ye Merry Gentlemen"/"We Three Kings" – Barenaked Ladies & Sarah McLachlan

The most recent song to make the list, this track takes two classic carols and mashes them up, turning them into a folk-rock jam that only the Barenaked Ladies could pull off. Sarah McLachlan's crooning doesn't hurt a bit, either. Unlike those ASPCA commercials. I'm just watching some "Matlock," then – BAM! – sad dogs.

10. "Christmas All Over Again" – Tom Petty and the Heartbreakers

Look, it's a Tom Petty song. I'm pretty sure he wasn't able to write a bad song. I'd listen to this song in August. Also, this song can serve as a warning to those who let the season sneak up on them. "Gotcha! You thought it was still fall? You thought you had until Thanksgiving? Think again, sucker! It's Christmas all over again, baby!"

9. "Rockin’ Around the Christmas Tree" – Brenda Lee

Brenda Lee was thirteen years old when she recorded this song. Thirteen! Do you know what I was doing when I was thirteen? Neither do I – but I can definitely say that I wasn't recording one of the best Christmas songs of all time, all while sounding like a world-weary 32 year old. On a different note, the saxophone solo is the third best saxophone solo in history, behind only "Baker Street" by Gerry Rafferty and another song on this list.

8. "White Christmas" – Bing Crosby

This is the best selling song of all time. According to Wikipedia, it's not even close, with "White Christmas" outselling "Candle in the Wind '97" by 17 million copies. This song came out 12 years before the film of the same name and was in fact written for a different film, "Holiday Inn" – which is the namesake for the Holiday Inn hotel chain. Not only is this the best selling song of all time, it also seems to be one of the most influential songs of all time, based on it's reach. That's pretty neat.

7. "Jingle Bell Rock" – Bobby Helms

I wanna go to a Jingle Hop. I don't even know what it is, but every time that Bobby Helms says that it has begun, I'm sad that I'm missing it.

6. "Christmas (Baby Please Come Home)" – Darlene Love

This is probably the best overall song on the list, due to the masterful production by Phil Spector, who has become a very problematic person in music history. Sticking to the track itself, the Wall of Sound has never sounded better, and Darlene Love's incredibly strong vocals push this song up into the upper echelon of Christmas tunes.

5. "Holly Jolly Christmas" – Michael Bublé

I had to put a Michael Bublé song on here, so I looked at the album listing, tried to pick one of them based off of merit, failed miserably and ended up randomly picking this song. It's a rockin' track, though, so I stand by it.

4. "All I Want for Christmas is You" – Mariah Carey

Everything that I could ever say about this song has already been said, so instead, enjoy Mariah Carey's new version of the music video, 25 years after the original release. I will choose to ignore the "SuperFestive" version, which features Justin Bieber, because it is not good.

3. "Santa Claus is Coming to Town" – Bruce Springsteen

Recently, I was riding in the car with my family, and this came on the radio. As it started, I began to recite the entire song, including the spoken word part at the beginning, the singing and the saxophone solo. I was given strange looks, and my family hasn't treated me the same since. No bother, though, because this is the saxophone solo that I mentioned earlier, and it is one for the ages. You guys know what time of year it is? Christmas time!

2. "A Charlie Brown Christmas" soundtrack – Vince Guaraldi Trio

What an incredibly large cop-out by me. Truth be told, had I not included the entire soundtrack as one listing, every single song would be listed individually. The album is twelve songs long, so half of the list would have been dominated by Charlie Brown. That would be no issue to me, but it would have been fair to the rest of the Christmas song canon. What can be said about "A Charlie Brown Christmas" that hasn't already been said? It's not only one of the best Christmas specials and albums of all time, but one of the best jazz albums of all time as well. Not too shabby for a blockhead.

1. "The Christmas Song (Chestnuts Roasting on an Open Fire)" – Nat King Cole

When I remember Christmas past, this is the song playing over my memories. Some people may not like how wistful the track is, but in my mind, it hearkens back to a time that we all wish existed, exists in our memories, but never truly existed. It's a time that we all wish had happened, a time that we all wish could happen again, but one that really never will happen. It's memories of a time that never went by, but one we wish could go by again. Of childhood innocence, of playing in the snow, of everything you could want at Christmastime. That's what this song represents. And it's the perfect representation of the spirit of Christmas.

With the big day almost upon us, the time to listen to Christmas music is coming to an end. Some say good riddance, others bid a fond farewell, but have no fear, the music will return next year. Probably sooner than you expect. Or want.