It's The Most Wonderful Music of the Year: A Guide to Christmas Music New and Old

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It’s the most wonderful time of the year, or something like that. With November now somehow in our rearview mirror, all of our attention has shifted to the holiday season, and it’s palpable. People are more cheerful, Christmas decorations are up, and most importantly, Christmas music is back in full force.

I know that my opinion – that Christmas music is the best thing about Christmas – isn’t universal, but you can’t deny the joy you feel when the right Christmas song comes on the radio, or is playing at the store, or is echoing down your snowy street. There’s just something magical about it.

I will admit, though, that I empathize with the disdain for this music. After all, we’ve been force fed the same Christmas carols and classics not only since Halloween, but pretty much our entire life. I can see how they can be a little stale, and trigger a Pavlovian-like response of disgust.

It is in light of this that I want to guide you through this seemingly monotonous season of holiday songs.


This is for those of you like me, who believe that there is no better Christmas music than the songs our parents and grandparents grew up with. The likes of Nat King Cole Bing Crosby, and Margaret Whiting, just to name a few, are the true soundtrack to this merry time and are likely to be heard at holiday markets, skating rinks, and centralized Christmas tree locations for the next month.

The weird thing about these songs is that they are so ubiquitous, yet I would guess that most people couldn’t tell you their names. Because of that, it’s not super easy to find the song you may be looking for, or the version you’re looking for. So instead of aimlessly searching, check out some of the playlists on Spotify, or YouTube. They are treasure troves of Christmas music and won’t leave you disappointed.


We just mentioned how it may not be super easy to locate the exact Christmas song you’re looking for. This can either be because you don’t know the actual name of the song, and a Google search is needed, or because there are so many covers of the classic, you don’t know which one you’re looking for.

Under normal circumstances, this would be classified as a major pain in the butt, but seeing as all (most) Christmas music is good Christmas music, this is a good problem to have.

Take, for example, the song “Have Yourself a Merry Little Christmas”. This song, originally sung by Judy Garland, is not only one of the most played Christmas songs, it’s one of the most covered songs, too. Frank Sinatra, Bing Crosby, and Ella Fitzgerald have all covered it, as have countless other artists.

Hell, Frank Sinatra, Bing Crosby, Dean Martin, Elvis Presley, and Nat King Cole, again, just to name a few, have entire albums dedicated to Christmas music. If you’re a fan of the classics but want to shake things up a bit, there’s more than enough to choose from.


The funny thing about Christmas music is that there is literally something for everyone. If you’re not into crooning, or big band music, or the general sound of the classics, chances are there is a band out there that has covered one of the classics in your preferred genre.

For example, Bela Fleck, a band that mixes jazz, bluegrass, and jam band sounds together, has one of my favorite versions of “Have Yourself a Merry Little Christmas”. There are no lyrics, but you will have absolutely no issue recognizing it and tapping your foot along with it. The same can be said for She & Him’s version of “Baby, It’s Cold Outside”.

It would be irresponsible for me to write a post about Christmas music and not include some of the newer tunes that this time of year has gifted us. Songs like Paul McCartney’s “Wonderful Christmas Time”, Wham’s “Last Christmas”, because there can never be too much synth, and of course, the best of the new bunch, “All I want For Christmas Is You” by the one and only Mariah Carey.

Don’t like Christmas music? You’re just not looking in the right place. There is something for everyone, you just gotta know where to find it.

Until next time – have yourself a merry little Christmas.

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When Arye isn't helping optimize your time, he is doing his part to ensure life is full of shenanigans.