We Made You a Winter Playlist

Here are eight songs that will help you get through, and actually enjoy, the coldest season.

Portland winters can be cold and depressing, with long nights and the “icy bike-chain rain” memorably described by poet and singer-songwriter David Berman. Yet it’s the season when the Pacific Northwest is at its most awe-inspiring, inundating residents with the presence of its ancient, vast landscape. Bundle up and enjoy this curation of songs intended for winter dreaming.

Kate Bush:

“Lake Tahoe”

Best enjoyed: Walking around a quiet residential neighborhood at night during a snowfall.

The English art-rock auteur’s 1985 song “Running Up That Hill” has been surging in popularity lately, but I would cast a dark-horse vote for the 2011 album 50 Words for Snow as her greatest work. On “Lake Tahoe,” she’s at the peak of her imaginative powers, using crystalline piano and sweeping orchestrations to tell the story of a spectral woman who emerges from the woods each night to look for her lost dog.

Vince Guaraldi Trio:

“Christmas Time Is Here (Vocal)”

Best enjoyed: In an armchair, inside, on a cold night with the lights dimmed.

In jazz pianist Vince Guaraldi’s astonishing A Charlie Brown Christmas soundtrack from 1965, you can feel both the comfort of a warm bed and the cold wind blowing outside. Tonally, there’s little else like it, and its centerpiece is “Christmas Time Is Here,” recorded both as a low-lying six-minute storm cloud and as a Christmas carol whose distant voices of children seem to have visited from the ancient past.

Pantha du Prince:

“Lay in a Shimmer”

Best enjoyed: Driving through a wintry landscape.

Listening to Pantha du Prince is like stepping into a fairy tale. The German producer’s 2010 album Black Noise conjures a slew of images straight out of a Brothers Grimm folk tale: magic woods, swan castles, trees coming to life. His style of techno deemphasizes the mechanical elements of the genre in favor of romantic gestures, and nearly all his work is surrounded by a swarm of bells that’s easy to imagine as a flurry of snowflakes.

Sufjan Stevens:

“Oh God, Where Are You Now? (In Pickerel Lake? Pigeon? Marquette? Mackinaw?)”

Best enjoyed: Looking out the bus window and pretending you’re in an indie movie.

2003′s Michigan rivals its big brother Illinois as Sufjan Stevens’ best album of the 2000s, alternating between proggy epics and hushed folk songs to evoke the icy majesty of the singer-songwriter’s home state. “Oh God, Where Are You Now?” combines the best of both worlds, a nine-minute evocation of a chilly landscape so severe and beautiful that it’s hard not to find echoes of God in it.

Willie Nelson:

“Moonlight in Vermont”

Best enjoyed: Deep in a dream.

Enriched by a brilliant arrangement from Booker T. Jones and a harmonica solo by Mickey Raphael that stings like a cold wind, Willie Nelson’s dusky 1978 version of the Great American Songbook standard “Moonlight in Vermont” astrally projects into the wilderness with visions of mountains and snowlight. It’s easy to dream along with him—especially after a glass of eggnog and/or some of Willie’s favorite herb.

Prince:

“Another Lonely Christmas”

Best enjoyed: When you’re so sad you actually kind of enjoy it.

Sad holiday songs are nothing new, but Prince’s wrenching 1984 song “Another Lonely Christmas” is one of the greatest of them all. Featuring an intro as violent as the one on Elvis’ “Blue Christmas” and some of the most striking images in his entire catalog of songwriting, the Purple One paints Minneapolis in winter as a landscape of beauty and despair while screaming, “You should be here!” as if raging against fate itself.

Tatsurō Yamashita:

“Christmas Eve”

Best enjoyed: At a joyous gathering where you have the AUX.

The Japanese lyrics are a bit of a bummer, but city-pop master Tatsuro Yamashita delivers them with such gusto and suavity that this 1983 song still feels celebratory. The English-language hook is as catchy as any Christmas standard, and the chords are just beautiful; this is a great example of how to capture both the Christmas spirit and the older, more primal connotations of winter in a single song.

Kath Bloom:

“Come Here”

Best enjoyed: Cuddling on a warm couch with someone you love (or with a pillow).

“There’s a wind that blows in from the north,” opens this exquisite 1984 folk-rock gem—and Kath Bloom, native to chilly Connecticut, knows a thing or two about cold winters. Maybe that’s why “Come Here,” best known for appearing in the 1995 romantic drama Before Sunrise, feels like a beacon of comfort. It’s the perfect song for moments when the whole world shrinks down to you and the person you’re holding.