Sorry SZA, it’s not cuffing season for everybody. It’s hard being single in the winter, which is already the darkest time of year (see the play on words there?). But personally, I think there’s something to be said about the quiet, almost beautiful comfort of sadness. So, guess what! I’ve gathered a collection of my favourite melancholic tunes to accompany your late-night cry.
Of course, my little playlist can’t help you with everything, so if your bouts of sadness last longer than a few days then I advise you to consult a professional.
But if you’re someone who knows that your own emotions are healthily temporary and you’d like a reference for when those darker, lonelier moments do arrive, please return to this lovely compilation.
“Both Sides Now” by Joni Mitchell
This song will never fail to be one of my all-time favourites. Released in 1966, it’s a classic in the folk genre, and Joni Mitchell’s a legend, recently winning the prestigious Gershwin Prize for Popular Song from the Library of Congress. Mitchell’s raw, earnest vibrato and sheer honesty audible in the heart-wrenching lyrics of “Both Sides Now” resonate on a deep level. It’s a profound meditation on the realization that life and love are more complicated than what we first bargained for.
“The Giver” by Sarah Kinsley
I’m sorry in advance, this song will hit you really damn hard when you first listen to it. As much as Joni Mitchell is a master at musical honesty, Sarah Kinsley almost harshly paints the full picture of the desperation in a, dare I say, situationship. Amongst the simple guitar that eventually builds to a warm soundscape, Kinsley’s voice wails like a siren who’s just had her heart broken. Regardless of whether you can directly relate to the lyrics of unrequited love, it’s a perfect song for sad times.
“Don’t Know Why” by Norah Jones
Norah Jones is also a fantastic go-to for a chill Sunday morning, but her most popular song is popular for a reason! As much as “Don’t Know Why” sounds like a light, jazzy tune on the surface, it’s actually addictively depressing. Jones’s breathy, flowing vocals detail a story of a lover she lost, or rather, one who left her when she “didn’t come”. If you also have some work to do in terms of taking a leap of faith and committing to relationships (like me), I’d recommend putting this song on repeat.
“cardigan – the long pond studio sessions” by Taylor Swift
We’re all Swifties here, so I know you know this one. In my opinion, the acoustic version of “cardigan” brings out the quietest, most intimate aspects of the song. Swift sounds more delicate in her storytelling with the sole accompaniment of a piano and a few subtle effects. And of course, the classic story of boy meets girl, boy betrays girl, boy and girl get back together is especially well told in “cardigan” from the perspective of a young, hopeful teenager. Although it’s technically happier than the other songs, “cardigan” is too pretty to exclude from this list.
“It Doesn’t Matter Anymore” by Eva Cassidy
“It Doesn’t Matter Anymore” is actually quite an old song. It was first recorded by Buddy Holiday in 1958, but Cassidy covers it with a newfound simplicity, which I think conveys the song’s message of an emotional break-up much more genuinely. Cassidy, unfortunately, passed in 1996 at the early age of 33, but her reputation as a songbird with natural technical skill lives on in her diverse jazz, blues and folk repertoire. Her melancholic, acoustic music has a particularly special place in my heart and this song is no exception.
“Let You Break My Heart Again” by Laufey
I discovered the jazz-inspired, Chinese-Icelandic singer Laufey this past summer, and she has held me in a chokehold ever since. Dreaming of love, nostalgia and heartbreak, Laufey has released some of the most beautiful songs that I’ve heard in the past few years. “Let You Break My Heart Again” is one such piece, blending her splendid vocals with an orchestral backing. It sounds as if you’re immersed in a Disney princess soundtrack, except for the fact that you’ve found yourself harbouring unrequited feelings (again).
“Waiting Room” by Phoebe Bridgers
I’ve saved the best for last. Suffice it to say, I’ve had Phoebe on repeat for the past month. It was her young, teenage self that wrote “Waiting Room”, and her youth is evident in the fervent vulnerability and relatability of the lyrics. In a song spanning over six minutes, Bridgers returns to the same phrase again and again: “I know it’s for the better”. It’s a tragic reminder to let fate work its path, despite how our emotions may plead otherwise.
While feeling heartbroken does undeniably suck, remember that it isn’t the end of the world. These songs reminded me of that and I hope they can help you too.