Right now, every Starbucks on every street corner in every city is piping Christmas music into your daily dose of caffeine. Cities appear to be alive and teeming with holiday cheer: Christmas tree lots are appearing, Salvation Army bell ringers are greeting you outside of Macy’s, and Fifth Avenue in New York City is sparkling with holiday displays. While the weather is unseasonably warm (nearly 70 degrees in D.C. at the end of November! ), now is still the time to curl up in front of a fireplace (or the TV Yule Log channel) and sip hot chocolate as you wait for rain, hail or snow to fall from the sky.

Tinsel and candy canes aside, December for me is more about the end of a year—the end of 12-months of laughter and tears, of dreams and failures. It’s a time to reflect on both the good and the bad, and to embrace all that we’ve endured as struggling, imperfect human beings.

Perhaps it’s depressing or morbid to be drawn to sad winter songs, but there’s something beautiful about the raw, emotional honesty in these songs and the way the artists dare to reveal such sadness during a time when we don’t want to think about sad things.


“River” by Joni Mitchell
Despite only minor references to the Christmas season (and a “Jingle Bell” intro), “River” has grown into one of the most popular songs you might hear at this time of year. It is largely a song about heartbreak and angst, and what better way to weather emotional turmoil during the holidays than with a little Joni? “River” is also one of Mitchell’s most covered tunes, with artists from Barry Manilow to Michelle Branch performing their own versions. The appeal of “River” lies in the melancholy imagery its lyrics evoke, with wishes of “a river I could skate away on” and trees being cut down from their natural homes to be taken indoors and loved in a new way.


“Winter Song” by Ingrid Michaelson and Sara Bareilles
If the song doesn’t make you think of snow and peppermint hot chocolate, then the music video will be enough to warm your heart. It’s a sweet and simple collaboration, with distinct harmonies and a sad story. “Winter Song,” like “River,” is another song about heartbreak around the holidays.


“Winter Bones” by Stars
The simple repetition of the instrumentals behind Amy Millan’s airy vocals strips away the traditional holiday cacophony of sleigh bells, carols and the “Auld Lang Syne” fanfare of the season. “The sun settles hard in the south, winter lives in my bones,” Millan sings. It’s as if Stars is begging us to embrace the hardships we’ve endured throughout the year so that we can prepare to begin anew.


“Winter” by Tori Amos
“Winter” is a nostalgic dedication to a father figure, and it’s something that I’m sure everyone can relate to (the desire to make somebody in their lives proud)—especially during the holidays, when everybody is taking the time to catch up with loved ones who’ve spent the year running around busy with work and school and life in general. But for me, there’s just something about Tori Amos’s voice that makes me want to curl up in bed with my unicorn PillowPet and read Holidays on Ice by David Sedaris. That’s really all I have to say about this song.