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10 Bittersweet Songs for Winter

Bon Iver, SYML, Keaton Henson, and More

Thanksgiving has come and gone, signaling the inevitable return of winter. With days full of family, friends, and happy memories, some nights all you want is to relax and unwind. So, whether it's cozying up by the fireplace or curling up on the windowsill to watch the snow, grab a blanket, a warm drink, and settle in to ten beautiful songs full of emotion.

"Above the Clouds of Pompeii" by Bear's Den

Whenever this song comes on, I want to take a drive up into the hills. If you don't listen to the lyrics, it almost sounds happy. This song has a deeply personal meaning to the artist, illustrating a conversation between him and his father. It's a piece on grieving and acceptance that will break your heart and piece it back together.

The line to listen for: 

"I was too young to understand the flowers slipping from your hands."

"You Don't Know How Lucky You Are" by Keaton Henson

I don't trust people that are dry-eyed by the end of this song. All of Henson's work is breath-taking and tragic, but this song blurs the line between personal experience and the universal emotion of heartbreak.

The line to listen for:

"Does his love make your head spin?"

"Fading Through" by Wafia, Vancouver Sleep Clinic

I had the chance to see Vancouver Sleep Clinic earlier this year, and what an experience it was. Tim Bettison's haunting voice compliments Wafia Al-Rikabi's angelic vocals perfectly. "Fading Through" is a song about missing someone dear, a feeling that often accompanies the holiday season.

The line to listen for:

"I'd climb on rooftops to catch a glimpse of the moona fading trail of you."

"Holocene" by Bon Iver

Okay, I could've put literally any song by Bon Iver. His songs are always full of layers and late-night introspection, but there's something special about snowy winter nights that lends to the feeling of accepted insignificance that Bon Iver explores in "Holocene."

The line to listen for:

"...And at once I knew I was not magnificent

Strayed above the highway aisle

(Jagged vacance, thick with ice)

I could see for miles, miles, miles."

"Where's My Love - Alternate Version" by SYML

The only thing more beautiful than the original is the alternative version, which swaps folksy guitar sound for a more heart-wrenching arrangement of piano and strings.

The line to listen for:

"Does she know that we bleed the same?"

"A Case of You" (Cover) by James Blake

Another song slowed down and set to piano. While the original by Joni Mitchell is irreplaceable, James Blake adds a new layer of depth and emotion to this classic.

The line to listen for:

"I could drink a case of you, darling, and I would still be on my feet."

"Winter" by Nieves

The combination of folk guitar and descriptive lyrics makes this song... not sad, exactly... but it definitely delivers a healthy dose of nostalgia. Not to mention the accent and style of the song gives it a sense of timelessness.

The line to listen for:

"You will migrate again I know it, but not to me."

"Michigan" by The Milk Carton Kids

Leaving behind something you used to love always creates a mixture of emotions. The Milk Carton Kids perfectly captures this dichotomy. "When it hurts most, it's the right thing."

The line to listen for:

"So when she calls, don't send her my way."

White Blood by Oh Wonder

If this song doesn't touch you, the backstory might. Written about a friend of the band who survived the removal of a cancerous brain tumor, it explores the human need for love and support.

This is the message posted on their official website:

"We wrote ‘White Blood’ to explore the idea of needing immunity from disease, sadness, hopelessness or fear, not only in the physical form of white blood cells, but also with simple human love and support. This song is for you, Steven and Wendi, and for anyone else out there that is dealing with difficult physical or mental health circumstances. We are all here for each other."

The line to listen for:

"Giving me your white blood, I need you right here with me."

Hopefully one of these songs made its way onto your winter soundtrack. I've linked my playlist of these songs and more here.