So, I didn’t really plan on my Top 25 Worst Christmas Songs list being as successful and as controversial as it ended up being. If I knew, like, a bunch of people were going to not only read it, but consider its contents, I would have put a lot more effort into it. I don’t mean that I’d change the order around or change what songs are on the list, but I’d probably write a little blurb for each one explaining why it sucks so much, and maybe a link to where you can listen to a version of it (if you’re THAT masochistic).
Well now you’re in luck! This is exactly what I’m doing with my much-asked-for 25 Best list which I’m presenting to you now. I will most likely go back and give similar treatment to my 25 Worst list, hopefully sometime before Christmas.

Finally, the good stuff.
THE TOP 25 CHRISTMAS SONGS OF ALL TIME
25. Blue Christmas
While the definitive version of this song was sung by Elvis in 1957, the song was actually recorded nine years earlier by Doye O’Dell, and made famous by Ernest Tubbs with his version in 1950. As an Elvis fan and as a fan of being lonely on Christmas, it’s almost always been a favorite of mine.
Ah, yes, the traditional English carols always get to me. This one’s from the 16th century and is actually taken from a play about the Gospel of Matthew, and is about the “massacre of the innocents”. What’s not to like?
While having all the haunting melodic structure of a traditional English carol, this one was actually written in 1933 in Appalachian North Carolina. It’s a true Christmas folk composition in every sense of the definition.
While the definitive version of the song is the Dean Martin version that he did for his Christmas album, the song’s been covered both successfully and unsuccessfully many, many times, and even won an Academy award when it appeared in MGM’s “Neptune’s Daughter” in 1949. Fun fact, in the original sheet music, it lists the two parts as “mouse” and “wolf”. Creepy.
How could I not like a song composed by Gustav Holst? Actually, Holst just did the music, whereas the “lyrics” were unsurprisingly a British Christmas poem written in 1872. Still, Holst.
20. We Three Kings Of Orient Are
Another British carol that’s really more of a hymnal–since it was written by a genuine reverend in the mid 19th century–beautifully contrasts minor and major melodies between the verses and chorus. It can be quite moving when not done at too fast a tempo.
Another ancient hymnal? Of course! Actually, the earliest that this one might date (both lyrics and music) as far back as the 8th century, but most realistically can be traced back to the 15th. Still, that’s pretty old, and was definitively finalized in the mid 19th, where all good music was finalized.
18. Please Come Home For Christmas
The original version of this is still the best, sung by Charles Brown in 1961, and easily satisfies both my love of depressing Christmas songs and the blues.
17. Away In A Manger
I didn’t realize this, but apparently this song has two completely different melodies, one written by Mueller and one by William Kirkpatrick. Both complement each other nicely, though, and collectively they get this song to #17.
Another traditional English carol, though much more upbeat than the others on my list. What’s nice about this one is that it’s more about the pagan winter tradition (both holly and ivy leaves are wiccan symbols of fertility) than the Christian themes usually displayed in the old English carols.
John Lennon’s message is pretty subtle, here; you might miss it if you’re not listening. I think what he’s trying to get across, is that screw war, seriously. Seriously people, it’s Christmas time, time to stop the war in ‘Nam. It’s actually just a really good song in general, though, and one of my favorites to listen to around the holidays.
14. Silver Bells
This classic was actually first sung by Bob Hope in the movie The Lemon Drop Kid, then later actually recorded by Christmas-master Bing Crosby. Favorite versions of mine include the Dean Martin and Sleeping At Last takes.
13. It Came Upon A Midnight Clear
Mid 19th century? Naturally, though the music to this one was written by Richard Storrs Willis, a composer who trained under Felix Mendelssohn, which is probably why it’s so good.
12. God Rest Ye Merry Gentlemen
Written in the style of a 15th century hymnal, this is one of those dark songs with positive lyrics that Charles Dickens hears and thinks, hey, I should reference this song in the book I’m writing. And so he did, in A Christmas Carol.
11. White Christmas
Irving Berlin’s 1941 song recorded first by Bing Crosby is not only a classic, but according to the Guinness Book of World Records, the best-selling single of all time. It’s one of those ones that can be over-played and covered in terrible ways, but it’s hard not to think of this as one of the simplest and celebrated Christmas tunes of all time.
Winter Wonderland is another one that’s been played to death and covered by lousy artists time after time, but is also still really good. The only Christmas-y lyric in the whole thing is the mention of “sleigh bells”, which is neat, and generally it’s the craftsmanship of the lyrics that sells me. With lines like “to face unafraid the plans that we’ve made”, how can you not be won over?
09. O Tannenbaum
Christmas trees were usually erected undecorated in celebration of the Germanic god Yule, then was later decorated with lights and changed to represent Christmas time, though the marriage of pagan and Christian themes was what inspired the writing of this song way back in the mid 17th century. The actual translation, by the way, isn’t “how lovely are your branches”, but rather a much more festive “your branches green delight us!” Indeed.
08. The First Noël
There are a lot of truly terrible versions of this song out there, much like with a couple other certain Christmas songs, sung in outlandishly diva-esque fashions that take attention away from the subtleties of the melody and focus it unjustly on the singer. Really the stirring melody presented in this (ahem) mid 19th century Cornish carol are what sell it.
07. Hark! The Herald Angels Sing
So, the lyrics to this were actually written in the mid 18th century as a traditional carol/hymnal/poem, but the music was actually written by one of my favorite composers, Felix Mendelssohn. Sure, Mendelssohn might’ve written the music to celebrate the advent of the printing press, but that’s pretty easy to forget when you combine it with the text of the pre-written poem.
A Charlie Brown Christmas is easily my favorite holiday movie (if you can even constitute something less than a half hour as a movie), and this is easily my favorite piece off of the album. It’s become a tradition to play Vince Guaraldi Trio pieces around the holidays solely because of their contributions on the soundtrack to this movie, and it’s no wonder why when you have fantastic pieces such as this.
05. Adeste Fideles
Otherwise known as “O Come All Ye Faithful”, this is one of the more powerful of the religiously-themed Christmas songs that I’ve come to enjoy. The traditional Latin is the only way to go with this one, and fortunately most 20th century artists agreed, including Bing Crosby, Frank Sinatra, and Perry Como.
04. I’ll Be Home For Christmas
This is quite possibly the most genuinely sad Christmas songs ever composed, and naturally one of my most dearly cherished. Actually composed by Jewish-American Walter Kent to reflect the soldiers’ attitudes during WWII (and one of the few good original songs to come off of Bing Crosby’s Christmas album), the song was almost destroyed completely when Josh Groban did a horrendous version of it in 2007. Seriously Josh, stop trying to kill Christmas.
03. Have Yourself A Merry Little Christmas
Another famous WWII Christmas tune, this song has been one of my favorites since childhood. It’s passionate, sad, and quietly hopeful. Originally written for the film Meet Me in St. Louis, the lyrics were much darker than when Frank Sinatra ordered a re-write on a few of the lines. “We’ll just have to muddle through somehow” was changed to “hang a shining star upon the highest bow” and so on, but all versions are fine by me.
02. O Holy Night
O Holy Night is by far my favorite religious Christmas song for a myriad of reasons. It singularly commands the reverence and powerful tradition of the holiday with a grand and hallowed sense of songwriting that isn’t seen in any of the other religious-type carols I’ve included on my list. The lyrics are superbly written, and even the terrible and over-played versions of these songs can be tolerable most of the time. Again, divas and folks like Josh Groban use this as an opportunity to stretch their vocal chords, but it’s completely unnecessary and detracts from the song itself. Perry Como’s version, in which he doesn’t try for hitting a high note at the end of the piece may be my favorite.
Sometimes referred to as “Chestnuts Roasting On An Open Fire”, this is pretty easily my favorite non-religious holiday song. Written by Mel Tormé (the Velvet Fog, as it were) and Bob Wells (composer of films like From Here To Eternity) in 1944, it represents all that was good about Christmas music in the WWII era of Christmas songs. Its message is simple, heartwarming, and hard to mishandle. Nat King Cole was the first to record it and his version is great, but so many versions of this song are great that it’s almost unprecedented in the genre, which is all the more reason why it’s not only stood the test of time, but remains my favorite Christmas song (of all time).

If you play this, then you are most certainly not a monster.
Hopefully it’s much easier for you to agree with what I consider to be “the best songs” as opposed to “the worst”, but something tells me that’s not going to happen.
#15 Happy XMAS? thought this was already discussed..grew up liking Nate King Cole one of grandpa’s favorite singers….but “my” #1 most disliked Christmas song is “Santa Baby” which haunts me everywhere I go….
“Happy Xmas” is verbatim what John Lennon titled it, just so we’re clear, I’m didn’t abbreviate it, he did.
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