Portland Monthly’s Essential Winter Playlist

Reimagined holiday classics, warm Americana, and rainy hip-hop by homegrown talent to keep you warm

By Conner Reed Published in the Winter 2020/2021 issue of Portland Monthly


hile we hunker down harder than we ever have this season, we're going to need reinforcements. Without a robust Netflix queue, a stacked Spotify library, and a strategic deployment of holiday sweets, we don't stand a chance. 

Portland Monthly doesn't have all the answers, but we do have some: once you've worn out our fall playlist, spin these warm, gentle tunes from Portlanders old and new—from The Decemberists to Y La Bamba to Rasheed Jamal and beyond—to pass the time a little more sweetly. (And be sure to follow us on Spotify for more mixes.)

“January Hymn,” The Decemberists

A dewy, calming cut from the Portland legends' R.E.M.-tinged LP The King Is Dead that includes such far-fetched lyrics as "maybe I should just let it be" and "on a winter Sunday I go to clear away the snow." 

“The Christmas Song,” Frankie Simone

A ghostly reimagining of the holiday classic, where Simone assures us "Santa's on her way / She and her bitches, queens, and baddies gonna slay." 

“Bet You Stay,” Reva DeVito

A smooth, rubbery R&B jam that radiates more heat than that half-assed porch heater ever will.

"Rain, Sleet, Snow," Paul Revere & The Raiders

This heavy original composition, from the ’60s novelty group's Christmas album, is a welcome reminder that they're good for more than just jangly Beatles/Beach boys redux. It's a scuzzy garage-rock gem, and maybe one of the best-ever songs about the mail. 

“Cinnamon Tree,” Esperanza Spalding 

The Grammy-winning jazz musician celebrates an essential winter spice in this sticky, irresistible number.

Esperanza Spalding

“Tell Me,” Johnny Jewel ft. Saoirse Ronan 

A tender lullaby penned by Portlander Johnny Jewel for the Ryan Gosling–directed film Lost River, in which four-time Academy Award nomine Saoirse Ronan plays a girl named Rat. 

“Winter’s Skin,” Y La Bamba

This seesawing waltz from the band’s 2010 release, Lupon, sounds like a bit like a big-band lullaby from outer space, which is to say it goes absolutely off.

“Ocho Kandelikas,” Pink Martini

The Portland stalwarts perform this Ladino Hanukkah song with fire, gusto, and just the right amount of cheese.

“Afternoon Rain,” Farnell Newton, Toranpetto, Tyrone Hendrix, and BrandonLee Cierley

A jazzy, spacey tune that makes lemonade from wet winter lemons and deserves a spot on every single writing/studying/chill-out playlist.

Old Records,” Cardioid

A raucous, bouncy cut from the deliberately unclassifiable rocker that calls to mind Mitski and Blondie at once. Perfect for a February bedroom singalong.

“Cookie Crumbles,” Fountaine

Leisurely piano-heavy hip-hop guaranteed to make you dream of summer.

Alela Diane

"Talk," Aminé feat. Saba

The Rose City rapper dropped a surprise deluxe edition of his late-summer album Limbo in early December, and this muscular track (with a feature from Chicago emcee Saba) is a bright spot—spare production puts Aminé's dexterous rhymes front and center where they belong.

You've Changed,” M. Ward

A rueful, lilting Billie Holiday cover from Ward's tribute album Think of Springit feels like he's whispering each word directly into your ear.

“Ether & Wood,” Alela Diane

A gorgeous lament from Diane's 2018 album Cusp; wise and wonderful Americana.

Scarred Up,” Daniyel

This cut from 18-year-old emo rapper's stunning March EP Madison High finds him in typically mournful spirits, with a fluttering guitar and crisp hi-hats that combine to evoke a well-stoked fireplace.

Manchild in Babylon,” Rasheed Jamal

The dizzyingly prolific Portland emcee put out two EPs and an album in 2020. This measured but confrontational track from The 3rd Idea effortlessly showcases his prodigious talent and benefits from the employment of lightly plucked strings.

Paul,” Tuesday Faust

Faust's October full-length Killed the Cat is brimming with playful, deceptively intricate songs, and "Paul," with its music box intro and lovestruck teenage lyrics, is one of the best. 

The Decemberists

Winter Machine,” Ezra Weiss

 A lively cut from the composer/pianist/PSU professor's 2006 album Persephone, full of brass and spirit.

Theme from The Valley of the Dolls,” k.d. lang

Speaking of don we now our gay apparel.... Lang's cover of the Dionne Warwick theme from the 1967 camp classic (canonically a Christmas movie) appeared on her 1997 record Drag, and that information would be enough to make it worth your time. Lucky for you, it's also super good: lush and tender, with a characteristically stunning vocal from Lang.

Living in Exile,” Sleater-Kinney

The all-time queens of "I can't believe this is happening and I'm gonna go ahead and scream about it" present a deeply relatable 9-months-deep-in-quarantine-and-counting mood. Parent album The Hot Rock's cover, a photo of the band crossing SW Broadway, makes this writer miss working downtown Portland ... a lot. 

Dance in the Rain,” A Strange Bird

Angelica Burdette, who performs as A Strange Bird, writes simple, gorgeous folk songs that she sings with breathless urgency. "I'll do whatever I need to get by / But I can't tell myself the world is dark, I need the sunshine," she croons here, extending flotation to anyone the winter threatens to drown.

Castleshell,” Dolphin Midwives

The electronic producer/harpist/delightful weirdo's 2019 full-length Liminal Garden is teeming with trippy, anxious soundscapes, and this is among the most exhilarating. It start beautiful, gets weird, then builds and builds until wrapping up with some ominous chimes. 

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