It’s hard to think of any time of year other than the holiday season that provides 24 hours worth of relevant songs.
I mean, summer has its songs, and each year we get the iconic “song of summer.” But it’s not really the same as this time – starting from around Thanksgiving and running through New Year’s – where day in and day out you can listen to all Christmas music, all the time.
It is probably no surprise to anyone that I go all in on this phenomena.
Do I want to listen to “I’ve Got My Love to Keep Me Warm” year-round? No, I do not. But on my holiday playlist, I have not just one, but several versions of that song, and I love them all.
As we wind down this holiday season, here are some of the songs I love, in no particular order, on my extensive holiday playlist, and why I love them. I highly recommend giving each a listen, and if you want to just borrow my holiday playlist on Spotify, the link is here.
1. “Last Christmas,” Wham! I know starting a holiday song list with a cheesy 80’s Christmas song is a bold move. But it was really this song that kicked off the incarnation of my playlist. I was listening to the radio 10 years ago or so, and they had this little jingle of “Christmas Classics!” And who was singing this retro tune? Bing Crosby? Dean Martin? Nope, George Michael! After I had a hearty laugh – Christmas classic! Are they for real?! – my childhood obsession with this song came back and has not left. As an added bonus, the music video is the ultimate 80’s ski trip along with some fabulous outerwear that I covet to this day.
2. “All I Want for Christmas Is You,” My Chemical Romance. Some of you might wonder: How could I slight Mariah like that? No slight to the Songbird, but My Chemical Romance takes her holiday song and makes it kick ass. It’s honestly what you’ve always wanted from the song and more.
3. “I Want an Alien for Christmas,” Fountains of Wayne. Let’s be real, there is probably a moment in life when each of us wanted a “little green guy about three feet high with 17 eyes who knows how to fly.” Fountains of Wayne was just strong and real enough to actually write about it. All kidding aside, this song is fun, silly, and totally rocks. My greatest musical disappointment in 2019 is that this song is no longer available on Spotify. I’m hoping that gets remedied in 2020.
4. “The Christmas Song,” The Raveonettes. It’s hard to break into the classic Christmas song world with a totally new song. But this song has become one of my favorites over the years. It has sweet, delicate harmonies that sweep into an interesting combination of a retro sound with some nice musical grit. Even lovelier, it catches that magical feeling of cuddling up with someone special when it’s cold out and not wanting to leave.
5. “Ner li,” Abigail Lapell and Laura Spink. This song is all that I love in any holiday song – simple harmonies and accompaniment, simple message. It’s a popular song in Israel and brings the message of Hanukkah that I love so much, that of light and how miraculous that one simple thing truly is. I wish this version was more widely available online, but I feel pretty lucky I get to listen to it anywhere.
6. “I’ve Got My Love to Keep Me Warm,” Billie Holiday. I think any day you get to listen to Billie Holiday is a day well spent. There is something especially magical in the romance of this time of year when it’s cold and you have that excuse to cuddle up. This song is the perfect soundtrack to some of the very best moments of winter in a way that only Lady Day could truly deliver.
7. “Christmas (Baby Please Come Home),” U2. The album “A Very Special Christmas,” which had Keith Herring’s art on the cover and so many incredible artists inside, made a whole generation rock out to holiday standards. But this song, covered by U2, pulls at your heart while really hitting you with strong vocals. Bono’s voice and the way he sings the lyrics gives us a space for the inevitable heartbreak of the season while giving us a great song to belt out in the shower.
8. “Goodnight My Baby,” Kingston Trio. The greatest Christmas album ever created is the Kingston Trio’s “Last Month of the Year.” It’s nearly criminal to have to pick just one song off the album, so I recommend pouring yourself an eggnog and listening to the whole thing end to end.
9. “Miracle,” Matisyahu. What I love about the religious side of this holiday season is the presence of miracles. Miracles are part of most religions and really, everyday life is pretty miraculous. I love the excuse to think about how incredible our world is and how lucky we are for so many things that just are. This song makes me look up with wonder.
10. “The Little Drummer Boy/Peace on Earth,” Bing Crosby and David Bowie. Getting to hear two breathtaking voices from two different eras harmonize is probably one of the greatest things ever. Really, listening to Bing Crosby and David Bowie harmonize is enough to put this song on any list. But some may argue the real greatness of this song is in the video in which Bowie pops over to the English estate next door to use Sir Percival’s piano (because clearly Bowie’s mansion couldn’t possibly contain a piano), meets the poor American relation and sings a duet with him. It’s like the Christmas carol version of a bad porn star plot.
11. “Santa Baby,” Eartha Kitt. Because, Eartha Kitt. If you need more reason for this song than that, then I think you need to reassess your priorities.
12. “Happy Xmas (War is Over),” Vanessa Carlton. I love this song because for me, it captures the introspection that comes at the end of the year. What have we done, what did we wish we did, how have we made our mark on the world in these 365 days, and the people that have made a mark in ours. While I love John Lennon and Yoko Ono’s original, this stripped down version by Vanessa Carlton really speaks to my heart and lets me find that space for introspection and thought that is so important as the end of the year draws near.