Snow is starting to fall, the sun won’t stop setting earlier and earlier, and we are all just trying to make it through to winter break. While everyone loves the holidays and it’s advertised as the season of joy, it can also bring up those nostalgic, bittersweet feelings that make the sad Christmas music just hit the hardest. So, I thought I’d recommend my top playlist picks that are perfect for those cold walks to class in the snow or long drives back in your hometown when you’ve never gotten over anything, ever.
- “‘Tis the damn season” – taylor swift
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This is the most obvious pick for me because it is a song about being home for the holidays and rethinking every decision you’ve ever made. While this isn’t the best feeling, I think it’s pretty relatable for most girls coming home from college and being surrounded by reminders of the past and what could have been. This song captures the emotions of this situation perfectly and will have you feeling all the nostalgia of your teenage heartbreaks.
- “Merry Christmas, Please don’t call” – Bleachers
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I have had this song on repeat since it came out and can verify it is the perfect addition to any melancholy holiday playlist. This song is a new release this year but it has the same nostalgia and warm Christmas vibe of classics like “Last Christmas” by Wham! which has made me fall in love with it. If you haven’t listened to Bleachers before, this is a great song to get started with, and chances are you’ve already heard Jack Antonoff’s production style through his work with artists like Taylor Swift, Lorde, and Lana Del Ray.
- “holidays” – Conan gray
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This is another new release for this year and it is a beautiful song about missing the innocence and simplicity the holidays had when you were a kid. Gray references the naïveté of not knowing how quickly life would change, which is a common way to feel as you return to your hometown and see how everyone you grew up with has gotten yet another year older and outgrown the town you once shared.
- “Cindy Lou Who” – Sabrina Carpenter
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While every song from Sabrina Carpenter’s Fruitcake EP is obviously fitting for the winter season, “Cindy Lou Who” is the standout for me and the perfect addition to any sad winter playlist. The references to Cindy Lou Who and one of the very first lines being, “There’s red and green everywhere, but I’m so blue,” really set the tone of this sad, yet festive song.
- “if we make it through December” – Phoebe Bridgers
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Phoebe Bridgers has released a multitude of heartbreaking, yet somehow comforting, Christmas covers over the years and they could make up the entirety of this list, but for simplicity’s sake, I picked just one for today. I chose her cover of “If We Make It Through December,” originally by Merle Haggard, because Bridgers paints the story so beautifully and her voice provides the smallest bit of hope as she sings, “If we make it through December, we’ll be fine.” I also strongly recommend her songs “So Much Wine,” “Christmas Song,” and “Day After Tomorrow,” which are all equally, heartbreakingly, beautiful.
- “One Last Song About Christmas” – The Goo Goo Dolls
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This is a more hopeful, uplifting, take on the loneliness of the holiday season and how it can actually bring us together, which makes it an important addition to your holiday playlist. “We don’t need a reason to love one another again” repeats as the song describes coming back to town and reuniting with old friends for the night, bonding over the love that was once shared.
- “snow angel” – reneé Rapp
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This is another one of my absolute favorite songs for the winter season and the recurring sentiment being, “I’ll make it through the winter if it kills me,” seems all too fitting as we’re all suffering through finals. If you’ve never listened to Reneé Rapp, this is a great introduction as it’s one of her best songs in my opinion, and showcases her insane vocal and songwriting abilities.
- “Christmas makes me cry” – Kacey Musgraves
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This song shares Musgrave’s sentimental take on Christmas and how the expectation of it being the happiest time of year can also make it feel like the loneliest. It comments on the bittersweet feeling of trying to be happy and smile through the holidays even when you feel like “the only one whose broken heart still has broken parts, just wrapped in pretty paper.”
- “River” – Joni Mitchell
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This is obviously one of the great, classic, sad Christmas songs that pretty much everybody knows, but I just couldn’t not include it in this list. This song echoes the sentiment of many others on this list of not enjoying the holidays as you feel you’re supposed to, and wanting to escape the weight of the season. The festive melody combined with the vulnerability in her voice as she sings, “I wish I had a river I could skate away on,” is enough to bring anyone to tears, and proves this song should never be left off a melancholic Christmas playlist.
- “Every holiday” – Mt. joy
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This song is a portrait of how dark and heavy the holidays can feel as they are often reminders of loss and bring unnecessary pressures. The piano in the background and unique vocals make this a very special, touching song for when you’re feeling down around Christmas.
I hope this list of some of my all-time favorite Christmas songs has given you some inspiration to curate your own sad girl Christmas playlist to set the perfect vibe for this winter season. These songs serve as an important reminder that it is still okay to feel all your feelings, even when it seems like you should be nothing but happy during the holidays. Whether you’re feeling lonely, nostalgic, or just weighed down by the holiday season, these songs should prove you are nowhere near alone in these feelings and you can always turn to music for some comfort.